Month: August 2020

Methyl 4-hydroxy-2H-thieno[2,3-e][1,2]thiazine-3-carboxylate 1,1-dioxide, cas is 98827-44-2, it is a common heterocyclic compound, the thiazines compound, its synthesis route is as follows.,98827-44-2

260 kg of 4-hydroxy-2H-thieno [2,3-e] -1,2-thiazine-3-carboxylic acid methyl ester 1,1-dioxide were dissolved in500kgDMF, add potassium carbonate 150kg, warmed to 140 C, and dropping 120kg of dimethyl carbonate, 2h drop end, after the dropwise addition, the reaction was continued for 5h, then add 140kg of potassium carbonate, dropping 300 kg of 2 – aminopyridine in dimethylformamide (DMF) (120kg 2-aminopyridine dissolved in 180 kg DMF), 2h addition was complete, the reaction was continued for 5h. After the reaction, cooling and filtering to remove potassium carbonate, the filtrate was recovered under reduced pressure most of the DMF, the residue was added mass concentration of 3% sodium hydroxide alkaline water, activated carbon bleaching, filtration, the filtrate was purified hydrochloric acid to pH = 3 -4, precipitated yellowish solid, centrifuged, the material was washed until neutral, dried, to give a yellow solid 276kg, yield 83%, product purity 99.85%.

With the rapid development of chemical substances, we look forward to future research findings about Methyl 4-hydroxy-2H-thieno[2,3-e][1,2]thiazine-3-carboxylate 1,1-dioxide

Reference£º
Patent; Jiangsu Engineering Polytechnic College; Yan Bin; Feng Chengliang; Guo Liqiang; (5 pag.)CN106916169; (2017); A;,
Thiazine – an overview | ScienceDirect Topics
Thiazine | C4H5NS – PubChem

Methyl 4-hydroxy-2H-thieno[2,3-e][1,2]thiazine-3-carboxylate 1,1-dioxide, cas is 98827-44-2, it is a common heterocyclic compound, the thiazines compound, its synthesis route is as follows.,98827-44-2

5.3 g of TNXK-3 and 20 ml of methanol were added to a reaction flask. Stir at room temperature. Separately add dimethyl sulfate 3.7 g methanol (5 ml) solution and 50% sodium hydroxide solution (5 ml). After the completion of the dropping, room temperature reaction 3 hours, cooling to 10 degrees, the water 50 ml dilution, use 10% hydrochloric acid to the PH is 3. Filtering, the filter cake after the water washing, drying, recrystallization with methanol, 60 degrees decompression drying, getting white solid 4.8 g, yield 86%.

With the rapid development of chemical substances, we look forward to future research findings about Methyl 4-hydroxy-2H-thieno[2,3-e][1,2]thiazine-3-carboxylate 1,1-dioxide

Reference£º
Patent; Jiangxi Yong Tong Technology Co., Ltd.; Liu Zhongchun; (13 pag.)CN107141308; (2017); A;,
Thiazine – an overview | ScienceDirect Topics
Thiazine | C4H5NS – PubChem

As a common heterocyclic compound, it belong thiazines compound,(S)-4-Hydroxy-2-(3-methoxypropyl)-3,4-dihydro-2H-thieno[3,2-e][1,2]thiazine-6-sulfonamide 1,1-dioxide,154127-42-1,Molecular formula: C10H16N2O6S3,mainly used in chemical industry, its synthesis route is as follows.,154127-42-1

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.

With the synthetic route has been constantly updated, we look forward to future research findings about (S)-4-Hydroxy-2-(3-methoxypropyl)-3,4-dihydro-2H-thieno[3,2-e][1,2]thiazine-6-sulfonamide 1,1-dioxide,belong thiazines compound

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

As a common heterocyclic compound, it belong thiazines compound,1,2-Thiazinane 1,1-dioxide,37441-50-2,Molecular formula: C4H9NO2S,mainly used in chemical industry, its synthesis route is as follows.,37441-50-2

4-Fluoro-2-(l ,1-dioxo-l lambda -[l,2]thiazinan~2-yl)bemonitrile. To a mixture of2,4-difluorobenzonitrile (10.0 g, 72 mmol) and l,l-dioxo-llambda6-[l,2]thiazin-2-ane (8.84 g, 65.4 mmol) in 1:1 tetrahydrofuran/dimethylformamide (40 mL) was added potassium carbonate (9.0 g, 65.4 mmol). The mixture was stirred at 90 0C for 18 h then filtered and concentrated. The residue was purified by flash chromatography (SiO2) eluting with 10%-50% ethyl acetate/hexanes followed by recrystallization from hot ethyl acetate/hexane to give the title compound as white needles (0.537 g, 3% yield). 1H NMR (500 MHz, CD3OD) 5 ppm: 7.70 (IH, dd, J= 8.8, 5.8 Hz), 7.30 (IH, dd, J= 8.8, 2.4 Hz), 7.15-7.12 (IH, m), 3.27 (2H, t, J= 5.3 Hz), 3.33 (2H, t, J= 6.1 Hz), 2.40-2.35 (2H, m), 2.05-2.01 (2H, m). LCMS (M+H) calcd for C11H16N2OF: 255.06; found: 255.19.

With the synthetic route has been constantly updated, we look forward to future research findings about 1,2-Thiazinane 1,1-dioxide,belong thiazines compound

Reference£º
Patent; BRISTOL-MYERS SQUIBB COMPANY; WO2007/64316; (2007); A1;,
Thiazine – an overview | ScienceDirect Topics
Thiazine | C4H5NS – PubChem

As a common heterocyclic compound, it belong thiazines compound,3,4-Dihydro-2H-benzo[b][1,4]thiazine,3080-99-7,Molecular formula: C8H9NS,mainly used in chemical industry, its synthesis route is as follows.,3080-99-7

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.

With the synthetic route has been constantly updated, we look forward to future research findings about 3,4-Dihydro-2H-benzo[b][1,4]thiazine,belong thiazines compound

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

As a common heterocyclic compound, it belong thiazines compound,3-Bromo-10H-phenothiazine,3939-23-9,Molecular formula: C12H8BrNS,mainly used in chemical industry, its synthesis route is as follows.,3939-23-9

In a 250 ml three-necked flask, 0.01 mol of raw material A1, 0.012 mol of raw material B1, 150 ml of toluene were added under a nitrogen atmosphere, and the mixture was stirred and mixed.Then, 0.03 mol of sodium t-butoxide, 5 ¡Á 10 -5 mol of Pd 2 (dba) 3, 5 ¡Á 10 -5 mol of tri-tert-butylphosphine was added, and the mixture was heated to 105 C, and refluxed for 24 hours.The sampling point plate shows that no raw material A1 remains, the reaction is complete; it is naturally cooled to room temperature, filtered, and the filtrate is steamed to a non-fraction (-0.09 MPa, 85 C) under reduced pressure, and passed through a neutral silica gel column to obtain an intermediate B1.HPLC purity 99.2%, yield 75.2%;

With the synthetic route has been constantly updated, we look forward to future research findings about 3-Bromo-10H-phenothiazine,belong thiazines compound

Reference£º
Patent; Jiangsu March Optoelectric Technology Co., Ltd.; Tang Dandan; Zhang Zhaochao; Li Chong; Zhang Xiaoqing; (44 pag.)CN108218853; (2018); A;,
Thiazine – an overview | ScienceDirect Topics
Thiazine | C4H5NS – PubChem

As a common heterocyclic compound, it belongs to quinuclidine compound,Quinuclidine-4-carboxylic acid hydrochloride,40117-63-3,Molecular formula: C8H14ClNO255,mainly used in chemical industry, its synthesis route is as follows.,3939-23-9

Tri-tert-butylphosphine (4.4 mL of a 1.0 M solution in toluene, 1.48 g, 0.05 mmol), palladium acetate (0.4 g,1.83 mmol) and sodium tert-butoxide (52.7 g, 549 mmol) were added to 2-6-a (20.423 g, 73.42 mmol) and 2-6-c(11.53 g, 73.42 mmol) a solution in degassed toluene (500 mL), and the mixture was warmed under reflux for 2 hr.The reaction mixture was cooled to room temperature, diluted with toluene and filtered over EtOAc. Dilute the filtrate with water and use aThe benzene was extracted and the organic phases were combined and evaporated under vacuum. The residue was passed through silica gel (heptane / dichloromethane)Filtration was carried out and crystallized from isopropanol. Obtaining 2-6-b 19.51 g, yield 75%; the resulting bromide 2-6-b(7.89 g, 20 mmol), pinacol borate (6.22 g, 24 mmol), 1,1′-bis(diphenylphosphino)-ferrocene-palladium dichloride(II) dichloromethane complex (0.49 g, 0.6 mmol), potassium acetate (5.90 g, 60 mmol) and 79 ml of toluene were reacted under refluxAfter 16 hours, cool, add 26 ml of water and stir for 30 minutes.The organic phase is separated and filtered through a short bed of diatomaceous earth, followed by organicThe solvent was distilled off and the crude product was recrystallized from heptane / toluene.The compound 2-6 was obtained in an amount of 6.58 g, yield 82%.

With the synthetic route has been constantly updated, we look forward to future research findings about 3-Bromo-10H-phenothiazine,belong thiazines compound

Reference£º
Patent; Changchun Hai Purunsi Technology Co., Ltd.; Zhang Hong; Cai Hui; (36 pag.)CN108530418; (2018); A;,
Thiazine – an overview | ScienceDirect Topics
Thiazine | C4H5NS – PubChem

As a common heterocyclic compound, it belongs to quinuclidine compound,Quinuclidine-4-carboxylic acid hydrochloride,40117-63-3,Molecular formula: C8H14ClNO32,mainly used in chemical industry, its synthesis route is as follows.,188614-01-9

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).

With the synthetic route has been constantly updated, we look forward to future research findings about Methyl 3-oxo-3,4-dihydro-2H-1,4-benzothiazine-6-carboxylate,belong thiazines compound

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

Methyl 3-oxo-3,4-dihydro-2H-1,4-benzothiazine-6-carboxylate, cas is 188614-01-9, it is a common heterocyclic compound, the thiazines compound, its synthesis route is as follows.,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)+.

With the synthetic route has been constantly updated, we look forward to future research findings about Methyl 3-oxo-3,4-dihydro-2H-1,4-benzothiazine-6-carboxylate,belong thiazines compound

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

As a common heterocyclic compound, it belongs to quinuclidine compound,Quinuclidine-4-carboxylic acid hydrochloride,40117-63-3,Molecular formula: C8H14ClNO364,mainly used in chemical industry, its synthesis route is as follows.,188614-01-9

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).

With the synthetic route has been constantly updated, we look forward to future research findings about Methyl 3-oxo-3,4-dihydro-2H-1,4-benzothiazine-6-carboxylate,belong thiazines compound

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