Flexible application of (S)-4-Hydroxy-2-(3-methoxypropyl)-3,4-dihydro-2H-thieno[3,2-e][1,2]thiazine-6-sulfonamide 1,1-dioxide in synthetic route

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. 154127-42-1, We look forward to the emergence of more reaction modes in the future.

A balanced equation for a chemical reaction indicates what is reacting and what is produced, but it reveals nothing about how the reaction actually takes place. The reaction mechanism is the process, or pathway, by which a reaction occurs.154127-42-1, name is :(S)-4-Hydroxy-2-(3-methoxypropyl)-3,4-dihydro-2H-thieno[3,2-e][1,2]thiazine-6-sulfonamide 1,1-dioxide. An updated downstream synthesis route of 154127-42-1 as follows.154127-42-1

Step H: 4(R)-ethylamino-3,4-dihydro-2-(3-methoxypropyl)-2H-thieno[3,2-e]-l,2- thiazine-6-sulfonamide- 1,1 -dioxide (I); To a solution of IX (41 g, 0.12 moles) and triethylamine (33 ml. 0.24 moles) in anhydrous tetrahydrofuran (615 ml) cooled to 0 to 5 C was added a solution of tosyl chloride (44 g, 0.24 moles) in tetrahydrofuran (205 ml). The mixture was allowed to warm to room temperature and stirred for 18 hours. The reaction mixture was cooled to 0 to 50C and ethylamine gas was purged from its 70% aqueous solution (365 ml) below 10C. Reaction mixture was allowed to attain ambient temperature and stirred for 36 hours. The reaction mixture was concentrated and ethyl acetate (615 ml) was added to it. Further the organic layer was washed with water (410 ml). The concentrated ethyl acetate layer and MDC (615 ml) was added followed by cooling to temperature 0 to 50C and 6M hydrochloric acid (600 ml) was added. The reaction mixture was stirred for 1 h at 15 to 20C. Aqueous layer was washed with MDC (205 ml). pH of the aqueous solution was adjusted to 8 using sodium bicarbonate solution causing white solid to precipitate which was extracted with ethyl acetate (2 x 410 ml). The ethyl acetate layer was evaporated to dryness to yield crude Brinzolamide (29g, 66%). Material was recrystallized from ethanol. [Purity: greater than 99.5%, m.p. 125-1270C], 154127-42-1

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. 154127-42-1, We look forward to the emergence of more reaction modes in the future.

Reference£º
Patent; USV LIMITED; WO2008/62463; (2008); A2;,
Thiazine – an overview | ScienceDirect Topics
Thiazine | C4H5NS – PubChem

 

Little discovery in the laboratory: a new route for 92-39-7

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it, 92-39-7.

Rate laws may be derived directly from the chemical equations for elementary reactions. This is not the case, however, for ordinary chemical reactions.92-39-7, name is :2-Chloro-10H-phenothiazine, below Introduce a new synthetic route.. 92-39-7

(1) Dehydration reaction: 2-chlorophenothiazine, cuprous cyanide, catalyst, quinoline, p-toluenesulfonyl chloride according to moleThe ratio is 1:1.25:0.15:5:0.1 is added to the reactor, and the temperature is raised to 120 C for dehydration reaction, the reaction is 1 hour, and the water is dehydrated to a moisture content of less than 0.1%;The catalyst is a mixture of sodium iodide and lithium iodide, and the molar ratio of sodium iodide to lithium iodide is 1:0.3;(2) Preparation of crude 2-cyanophenothiazine: the temperature of the reactor was raised to 230 C, and the reaction was carried out for 15 hours;(3) Separation of crude 2-cyanophenothiazine: the reactor temperature was lowered to 90 C, and 8 times was added to the reactor.The total amount of moles of the starting material is water, the solid is precipitated and filtered, and the product is extracted with ethyl acetate and concentrated to dryness to give a crude 2-cyanophenothiazine;(4) Purification of 2-cyanophenothiazine: a crude 2-cyanophenothiazine is placed in a mixed solvent of toluene and methanol,The volume ratio of toluene to methanol in the mixed solvent was 1:0.15, the temperature was raised to 120 C for 30 minutes, and the mixture was cooled to 20 C, and the precipitated solid was filtered to obtain 2-cyanophenothiazine.After testing, the yield of 2-cyanophenothiazine prepared in this example was 92.6%, and the purity of the product was 99.61%.The content of the amide was 0.03%.

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Reference£º
Patent; Ningbo Jinuo Chemicals Co., Ltd.; Peng Zhigang; Yue Mingxin; Qu Qiangzheng; (8 pag.)CN105175355; (2018); B;,
Thiazine – an overview | ScienceDirect Topics
Thiazine | C4H5NS – PubChem

 

Fun Route: New Discovery of 1,2-Thiazinane 1,1-dioxide

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand 37441-50-2 reaction routes.

The major producers of chemicals have been the Europe, Japan and China. Due to the growing call for a cleaner, 37441-50-2, greener environment, people will have to find innovative ways to maintain their relevance. Here is a downstream synthesis route of the compound 37441-50-2, name is :1,2-Thiazinane 1,1-dioxide

8-HYDROXY- [1, 6] naphthyridine-7-carboxylic acid methyl ester 1A. 4 (WO 0230930 A2, p. 171) is reacted with one molar equivalent of N-bromosuccinimide in dichloromethane, to yield 5-BROMO-8-HYDROXY- [1, 6] NAPHTLIYRIDINE-7-CARBOXYLIC acid methyl ester, 1A. 5. The phenol is then reacted with p-toluenesulfonyl chloride and triethylamine in CHLOROFONN, FOR example as described in WO 02 30931 A2 p. 72, to give 5-bromo-8- (toluene-4-sulfonyloxy)- [1, 6] naphthyridine-7-carboxylic acid methyl ester 1A. 6. The product is then reacted with [1, 2] thiazinane 1, 1-dioxide 1A. 7 and cuprous oxide in pyridine at reflux, for example as described in WO 0230931 A2, p. 73, to produce 5- (1, 1-DIOXO- 1,2] thiazinan-2-yl)-8- (toluene-4-sulfonyloxy)- [1, 6] naphthyridine-7-carboxylic acid methyl ester 1A. 8. Deprotection, for example by reaction with methanol sodium methoxide in DIMETHYLFORMAMIDE, as described in WO 0230931 A2 p. 74, then affords the phenol 1A. 9., 37441-50-2

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand 37441-50-2 reaction routes.

Reference£º
Patent; GILEAD SCIENCES, INC.; WO2005/28478; (2005); A1;,
Thiazine – an overview | ScienceDirect Topics
Thiazine | C4H5NS – PubChem

 

Derivation of elementary reaction about (S)-4-Hydroxy-2-(3-methoxypropyl)-3,4-dihydro-2H-thieno[3,2-e][1,2]thiazine-6-sulfonamide 1,1-dioxide

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154127-42-1. Rate laws may be derived directly from the chemical equations for elementary reactions. This is not the case, however, for ordinary chemical reactions.154127-42-1, name is :(S)-4-Hydroxy-2-(3-methoxypropyl)-3,4-dihydro-2H-thieno[3,2-e][1,2]thiazine-6-sulfonamide 1,1-dioxide, below Introduce a new synthetic route.

Step J: (+)-4-Ethylamino-3,4-dihydro-2-(3-methoxy)propyl-2H-thieno[3,2-e]-1,2-thiazine-6-sulfonamide-1,1-dioxide hydrochloride To a solution of the product from Step I (2.4 g, 6.74 mmol) and triethylamine (3.8 mL, 27 mmol) in anhydrous tetrahydrofuran (20 mL) cooled to -20 C. was added tosyl chloride (2.6 g, 13.5 mmol); this mixture was allowed to warm to room temperature and stirred for 18 hr. The reaction mixture was cooled to -60 C. and ethylamine (10 mL) was added and the mixture was again allowed to warm to room temperature. After 18 hr the reaction mixture was diluted with ethyl acetate (200 mL), washed with a saturated aqueous solution of sodium bicarbonate (3*50 mL), dried (MgSO4), and evaporated to give the crude product which was purified by column chromatography [silica; CH3 OH/CH2 Cl2 (20:1)] to give 1.3 g (52%) of the desired amine. The free base was dissolved in ethanol (5 mL) and treated with a 2M solution of hydrochloric acid in ethanol (4 mL) at room temperature. Evaporation of the solvent provided a solid which was recrystallized from methanol: methylene chloride to give 950 mg (34%) of the desired product; mp 175-177 C.; [~]D +10.35 (C=1.00, H2 O). Analysis. Calculated for C12 H22 ClN3 O5 S3: C, 34.32; H, 5.28; N, 10.00 Found: C, 34.26; H, 5.23; N, 9.92.

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Reference£º
Patent; Alcon Laboratories, Inc.; US5378703; (1995); A;,
Thiazine – an overview | ScienceDirect Topics
Thiazine | C4H5NS – PubChem

 

Derivation of elementary reaction about 2-Chloro-10H-phenothiazine

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92-39-7. Rate laws may be derived directly from the chemical equations for elementary reactions. This is not the case, however, for ordinary chemical reactions.92-39-7, name is :2-Chloro-10H-phenothiazine, below Introduce a new synthetic route.

Step: Step 1, the reaction system azeotropic water removal: To the reaction kettle with argon gas was added 50 kg of N-methylpyrrolidone at room temperature, 2-chlorophenothiazine 50 kg, cuprous cyanide 23 kg, lithium iodide 0.23 kg, potassium iodide 3.55 kg and cyclohexane 25 kg, Stirring up to 85C , boiling a total of boiling water, about 40min, measured water 0.04wt.% (Moisture ? 0.05wt.%). Step 2: Preparation of 2-cyanophenothiazine by refluxing reaction: The reaction system after the removal of water continued to warm to 112 C, Atmospheric distillation distillation system in the cyclohexane, cyclohexane can be recycled recycling, Continue to heat up to the reflux state (T = 218 ), insulation reaction 10h, To obtain a reaction product; Step 3, the reaction product after treatment and extraction: After the reaction, the temperature was lowered to 75 C, To the reaction system was added sodium thiosulfate solution (sodium thiosulfate 33 kg and water 250 kg mixed dissolved) Stirring for 2h, cooling to 5 , filtering, the first filter cake and the first filtrate, The first filter cake was dried at 90 C to a moisture content of ? 4 wt.%. The first filter cake was extracted with acetone, The dried cake and acetone 700L, heated to reflux 30min, down to 50 , The second filter cake and the second filtrate were filtered and the second filtrate was concentrated at atmospheric pressure to give 500 L of acetone to give a concentrate, The concentrated liquid for low temperature precipitation, the specific process is to concentrate the solution to 0 , filtration, Dried 2-cyanophenothiazine crude 45kg, 98% purity, amide impurity 0.9%.Step 4: Purification of crude 2-cyanophenothiazine: 2-cyanophenothiazine crude 45kg and acetone 36kg heated to reflux, reflux insulation 30min. Cooled to 0 C, filtered and dried to give 4-cyano phenothiazine 43.2 kg, purity ?99% Amide impurities ? 0.1%, yield: 90.0%This example gives an industrial preparation method of an environment-friendly 2-cyanophenothiazine, The method of other processes and implementation Example 1 is the same, the difference is only: In the third step, the mass of the dried first filter cake and the ratio of the second organic solvent acetone used in the first filter cake Was adjusted to 1:15 from 1: 8 of Example 1. The yield of 2-cyanophenothiazine was 90.2% based on 2-chlorophenothiazine

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Reference£º
Patent; Xi’an Caijing Optoelectric Technology Co., Ltd.; Gao Aiai; Zhao Qunxing; Zhou Bugao; Fan Jia; Bie Guojun; Yan Xiaoliang; Lan Aihu; Guo Chuang; Li Jian; Xu Lei; Zhang Weijie; Wang Li; (11 pag.)CN106946811; (2017); A;,
Thiazine – an overview | ScienceDirect Topics
Thiazine | C4H5NS – PubChem

 

Flexible application of Methyl 3-oxo-3,4-dihydro-2H-1,4-benzothiazine-6-carboxylate in synthetic route

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An elementary termolecular reaction involves the simultaneous collision of three atoms, 188614-01-9, molecules, or ions. Here is a downstream synthesis route of the compound 188614-01-9, name is :Methyl 3-oxo-3,4-dihydro-2H-1,4-benzothiazine-6-carboxylate

A. 3-Oxo-3,4-dihydro-2H-benzo[1,4]thiazine-6-carboxylic acid. To a solution of 3-oxo-3,4-dihydro-2H-benzo[1,4]thiazine-6-carboxylic acid methyl ester (1.5 g, 6,7 mmol) in a THF/H2O mixture (1:1, 63 mL) was added 4 N LiOH (8.0 mL, 32 mmol) and the resulting solution was stirred at RT for 24 h. The solution was partially concentrated and diluted with H2O (50 mL). The solution was acidified using concentrated HCl and a solid precipitated. The solid was collected via filtration, washed with H2O and dried in vacuo to provide 0.79 g (60%) of the title compound as a white solid. MS (ESI): exact mass calculated for C9H7NO3S, 209.01; m/z found, 210.2 [M+H]+. 1H NMR (500 MHz, CD3OD): 7.65-7.61 (m, 2H), 7.40 (d, J=8.1, 1H), 3.48 (s, 2H).

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Reference£º
Patent; Allison, Brett D.; Gomez, Laurent; Grice, Cheryl A.; Hack, Michael D.; Morrow, Brian J.; Motley, S. Timothy; Santillan, Alejandro; Shaw, Karen J.; Schwarz, Kimberly L.; Tang, Liu Y.; Venkatesan, Hariharan; Wiener, John J. M.; US2006/223810; (2006); A1;,
Thiazine – an overview | ScienceDirect Topics
Thiazine | C4H5NS – PubChem

 

Little discovery in the laboratory: a new route for 188614-01-9

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand 188614-01-9 reaction routes.

We know that the rate of many reactions can be accelerated by catalysts. A catalyst speeds up the rate of a reaction by lowering the activation energy; in addition, the catalyst is regenerated in the process. 188614-01-9, name is :Methyl 3-oxo-3,4-dihydro-2H-1,4-benzothiazine-6-carboxylate, below Introduce a new synthetic route.. 188614-01-9

Step 1. Borane-tetrahydrofuran complex solution (1 M in tetrahydrofuran, 45 mL, 45 mmol) was added at 0 C. to a suspension of methyl-3-oxo-3,4-dihydro-2H-1,4-benzothiazine-6-carboxylate (2.00 g, 8.96 mmol) in tetrahydrofuran (20 mL). The ice bath was removed, the homogenous solution stirred at room temperature for 2 h, then excess reagent was destroyed by careful addition of methanol (42 mL) at 0 C. After evaporation of volatile material, the residue was taken up in 5% methanolic sulfuric acid solution (25 mL) and the solution was heated at reflux over 80 min. After cooling, the reaction mixture was partitioned between ethyl acetate and water, the organic layer was dried (MgSO4) and evaporated to produce 3,4-dihydro-2H-benzo[1,4]thiazine-6-carboxylic acid methyl ester (1.79 g, 96%). Light yellow solid, MS (ISP)=210.1 (M+H)+., 188614-01-9

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand 188614-01-9 reaction routes.

Reference£º
Patent; Ackermann, Jean; Bleicher, Konrad; Ceccarelli, Simona M.; Chomienne, Odile; Mattei, Patrizio; Sander, Ulrike Obst; US2007/191603; (2007); A1;,
Thiazine – an overview | ScienceDirect Topics
Thiazine | C4H5NS – PubChem

 

The effect of 2-(Trifluoromethyl)-10H-phenothiazine reaction temperature change on equilibrium

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A heterogeneous catalyst is a catalyst that is present in a different phase than the reactants. Such catalysts generally function by furnishing an active surface upon which a reaction can occur. 92-30-8, name is :2-(Trifluoromethyl)-10H-phenothiazine, introduce a new downstream synthesis route as follows. 92-30-8

Compound 21; 10-(4-chlorobutyl)-2-trifluoromethylphenothiazine; To a stirred solution of 2-trifluoromethylphenothiazine 1 (4.Og, 15 mmol), sodium hydride (1.2g, 24 mmol) in dry toluene (40 mL), 1-bromo 4- chlorobutane (3.0 g, 17.6 mmol) was added. The reaction mixture was stirred for 18 hours at 110 C under an atmosphere of argon. The solution was cooled to room temperature and poured into an ice-water mixture. The crude product was extracted with ethyl acetate (3chi50mL) and the organic phase was dried over sodium sulphate. Final purification was performed by column chromatography (9: 1 hexane: ethyl acetate) on silica gel to give 21 (3.5 g, 65% ) as an oil., 92-30-8

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Reference£º
Patent; IMMUNE CONTROL, INC.; WO2008/27521; (2008); A1;,
Thiazine – an overview | ScienceDirect Topics
Thiazine | C4H5NS – PubChem

 

Derivation of elementary reaction about 92-30-8

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand 2-(Trifluoromethyl)-10H-phenothiazine reaction routes.

Rate laws may be derived directly from the chemical equations for elementary reactions. This is not the case, however, for ordinary chemical reactions.92-30-8, name is :2-(Trifluoromethyl)-10H-phenothiazine, below Introduce a new synthetic route.. 92-30-8

Compound 13; 10-[3-(N-Boc-4-piperidyl)propyl]-2-trifluoromethylphenothiazine; To a stirred solution of 2-trifluoromethylphenothizine 1 (400 mg, 1.5 mmol), sodium hydride (100 mg, 2 mmol) in DME (10 mL) at 90 C was added N- Boc-4-(3-bromopropyl)piperidine 12 (380 mg, 1.24 mmol) dropwise under an atmosphere of argon. The reaction mixture was stirred for 12h at reflux. The reaction mixture was filtered and the filtrate was concentrated under vacuum. The residue was partitioned between ethyl acetate (25 mL) and brine (1OmL). The organic layer was dried over anhydrous sodium sulphate, filtered, and evaporated. The resulting residue was purified by silica gel column chromatography (8:2 hexane : ethyl acetate) on silica gel to give phenothiazine derivative 13 (425 mg, 70percent) as a solid. MS(ESI): m/z493 (M+H).

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand 2-(Trifluoromethyl)-10H-phenothiazine reaction routes.

Reference£º
Patent; IMMUNE CONTROL, INC.; WO2008/27521; (2008); A1;,
Thiazine – an overview | ScienceDirect Topics
Thiazine | C4H5NS – PubChem

 

Research on new synthetic routes about 3,4-Dihydro-2H-benzo[b][1,4]thiazine

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3080-99-7, A balanced equation for a chemical reaction indicates what is reacting and what is produced, but it reveals nothing about how the reaction actually takes place. The reaction mechanism is the process, or pathway, by which a reaction occurs.3080-99-7, name is :3,4-Dihydro-2H-benzo[b][1,4]thiazine. An updated downstream synthesis route of 3080-99-7 as follows.

To a round bottom flask charged with compound 16-1 (151 mg, 1.0 mmol) and methyl 4-(bromomethyl)benzoate (228 mg, 1.0 mmol) in DMF (5 mL) was added K2CO3 (276 mg, 2.0 mmol). The resulting mixture was allowed to stir for 2 h at 80 C. The mixture was cooled to room temperature and after addition of water (15 mL) extracted with EtOAc (3 x 15 mL). The combined organic extracts were washed with brine (20 mL), dried over sodium sulfate, and concentrated under vacuum. The crude product was purified by flash chromatography (0 – 50% EtOAc/hexanes) to afford as colorless oil (110 mg, 37%).1H NMR (CDCI3) delta 8.00, 7.33 (AlphaAlpha’ChiChi’ multiplet, AX + J AX = 8.4 Hz, 4H), 7.08 (dd, / = 7.7 Hz, 1.5 Hz, 1H), 6.90 (incompletely resolved ddd approaching dt, average of two larger / = 7.8 Hz, additional / = 1.1 Hz, 1H), 6.63 (incompletely resolved ddd approaching dt, average of two larger / = 7.5 Hz, additional / = 0.8 Hz, 1H), 6.54 (dd, 7 = 8.3 Hz, 0.7 Hz, 1H), 4.57 (s, 2H), 3.90 (s, 3H), 3.69, 3.08 (AlphaAlpha’ChiChi’ multiplet, AX + J AX = 10.4 Hz, 4H). 13C NMR (CDCI3) delta 166.9, 143.8, 143.4, 130.1 (2C), 129.1, 128.0, 126.6 (2C), 126.1, 118.0, 117.8, 113.2, 56.3, 52.1, 50.6, 25.9. ESI LRMS: [M+H]+, mlz 300.2., 3080-99-7

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Reference£º
Patent; THE BOARD OF TRUSTEES OF THE UNIVERSITY OF ILLINOIS; KOZIKOWSKI, Alan; SHEN, Sida; BERGMAN, Joel; (100 pag.)WO2017/142883; (2017); A1;,
Thiazine – an overview | ScienceDirect Topics
Thiazine | C4H5NS – PubChem