Day: October 21, 2020

92-30-8 A common heterocyclic compound, 92-30-8,2-(Trifluoromethyl)-10H-phenothiazine, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route.

After dissolving 2-(trifluoromethyl)-10H-phenothiazine (2.0 g, 7.48 mmol) in N,N-dimethylformamide (2 mL), 60% sodium hydride (149.70 mg, 3.74 mmol) and 1-bromo-4-chlorobutane (1.16 mL, 10.10 mmol) were added at 0 C. The reactants were heated at 100 C. for 12 hours under reflux. After the reaction was completed, the reaction solution was extracted with ethyl acetate and the organic layer was dried with magnesium sulfate, filtered under reduced pressure and then concentrated under reduced pressure. The target compound (1.52 g) was obtained with a yield of 56.72% by separating the residue by chromatography (ethyl acetate/n-hexane=1/20). 1H NMR (400 MHz, CDCl3): delta 1.89-2.00 (4H, m, 2CH2), 3.40 (1H, t, J=6.02 Hz, CH), 3.54 (1H, t, 6.18 Hz, CH), 3.94 (2H, t, 6.02 Hz, CH2), 6.89 (1H, d, J=8.12 Hz, CH), 6.96 (1H, t, 7.44 Hz, CH) 7.03 (1H, s, CH), 7.13-7.17 (2H, m, 2CH), 7.21 (2H, t, 8.16 Hz, 2CH).

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 92-30-8 reaction routes.

Reference£º
Patent; Korea Institute of Science and Technology; Roh, Eun Joo; Jeon, Bo Ra Mi; Lee, Chang Joon; Hong, Jin Pyo; Jeong, Joo Yeon; Kang, Sang Soo; (28 pag.)US10035795; (2018); B1;,
Thiazine – an overview | ScienceDirect Topics
Thiazine | C4H5NS – PubChem

3939-23-9, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact.3939-23-9,3-Bromo-10H-phenothiazine, it is a common compound, a new synthetic route is introduced below.

2, under nitrogen protection will be prepared in step 1 p-phenylenediamine and phenothiazine derivatives according to 1:1 molar ratio was added to toluene, while adding potassium tert-butyl alcohol and palladium acetate as a catalyst,The reaction was heated to 80 C for 3 hours and then cooled to room temperature. The reaction was filtered,The filtrate was washed with dichloromethane and then the solvent was evaporated to dryness. The crude product was repeatedly washed with methanol and acetone,The product is obtained after purification by column chromatography.

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 3-Bromo-10H-phenothiazine reaction routes.

Reference£º
Patent; Changchun Hai Purunsi Technology Co., Ltd.; Guo Jianhua; (12 pag.)CN106831645; (2017); A;,
Thiazine – an overview | ScienceDirect Topics
Thiazine | C4H5NS – PubChem

37441-50-2,Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps,and cheap raw materials.37441-50-2,A new synthetic method of this compound is introduced below.

A stirred mixture of methyl 6-BROMO-3-HYDROXYPYRIDINE-2-CARBOXYLATE (6.15 g, 26.5 mmol), 8-sultam (described in WO 02/30931-A2, Merck & Co. , Inc. , 2002) (3. 98 g, 29.4 mmol) and copper (I) oxide (5.75 g, 40.2 mmol) in anhydrous pyridine (100 mL) was heated at 130 C, under argon, for 6 h. The mixture was cooled, and the pyridine removed under reduced pressure. The residue was treated with CH2C12 (400 mL) and EDTA (0.35 M in H20, 300 ML, 105 mmol) and air was bubbled into the mixture for 18 h. The mixture was filtered through a pad of celite and the aqueous layer was saturated with solid NACI and extracted with CH2CLZ (4 x 250 mL). The combined organic extracts were dried (NA2S04), filtered, and concentrated in vacuo to afford a crude oil. The oil was dissolved in MEOH (400 mL) and conc. H2S04 (2 ML) and heated to reflux for 18 h, then allowed to cool to ambient temperature. Most of the solvent was removed in vacuo and the residual mixture was partitioned between CHZCLX (400 mL) and saturated NAHCO3 (400 mL). The aqueous layer was extracted further with CH2Cl2 (2 x 250 mL) and the combined organic extracts were dried (NA2S04), filtered, and concentrated in vacuo to afford a crude sample of the product. This crude product was partially purified by silica gel chromatography, eluting with a gradient of CH2C12 : MEOH-100 : 0 to 95: 5 to give a yellow solid that was crystallized from MEOH to afford the title compound as a pale yellow solid of sufficient purity for use in the next step. MS: FALZ = 287 (M + 1).

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, 1,2-Thiazinane 1,1-dioxide.

Reference£º
Patent; MERCK & CO., INC.; WO2005/9962; (2005); A1;,
Thiazine – an overview | ScienceDirect Topics
Thiazine | C4H5NS – PubChem

In the chemical reaction process,reaction time,type of solvent,can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product.An updated downstream synthesis route of 37441-50-2,1,2-Thiazinane 1,1-dioxide, as follows.37441-50-2

To a mixture of 2,4-difluorobenzonitrile (10.0 g, 72 mmol) and 1,1-dioxo-1?6-[1,2]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 C. 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) ? ppm: 7.70 (1H, dd, J=8.8, 5.8 Hz), 7.30 (1H, dd, J=8.8, 2.4 Hz), 7.15-7.12 (1H, 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.

According to the analysis of related databases, 1,2-Thiazinane 1,1-dioxide, the application of this compound in the production field has become more and more popular.

Reference£º
Patent; Naidu, B. Narasimhulu; Banville, Jacques; Beaulieu, Francis; Connolly, Timothy P.; Krystal, Mark R.; Matiskella, John D.; Ouellet, Carl; Plamondon, Serge; Remillard, Roger; Sorenson, Margaret E.; Ueda, Yasutsugu; Walker, Michael A.; US2005/267105; (2005); A1;,
Thiazine – an overview | ScienceDirect Topics
Thiazine | C4H5NS – PubChem

In the chemical reaction process,reaction time,type of solvent,can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product.An updated downstream synthesis route of 37441-50-2,1,2-Thiazinane 1,1-dioxide, as follows.37441-50-2

A flask was charged under nitrogen with 1,1-dimethylethyl 3-bromo-5-iodobenzoate (D7)(1 g, 2.6 mmol, 1 equiv), Cs2CO3 (1.26 g, 3.9 mmol, 1.5 equiv),tris(dibenzylideneacetone)dipalladium(0) (12 mg, 0.013 mmol, 0.005 equiv), Xantphos (22 mg, 0.038 mmol, 0.015 equiv) and toluene (20 ml). Tetrahydro-2H-1,2-thiazine 1,1-dioxide (D6) (350 mg, 2.9 mmol, 1.1 equiv) was then added and the resulting mixturewas stirred at 100C for 16 h then cooled to room temperature and diluted with AcOEt.The organic phase was washed with saturated aqueous NaHCO3 solution, dried overMgSO4 and concentrated in vacua. The residue was triturated with Et2O to give 1,1-dimethylethyl 3-bromo-5-(1,1-dioxidotetrahydro-2/-/-1,2-thiazin-2-yl)benzoate (D8) (590mg, 58%) as a white solid.

According to the analysis of related databases, 1,2-Thiazinane 1,1-dioxide, the application of this compound in the production field has become more and more popular.

Reference£º
Patent; GLAXO GROUP LIMITED; WO2004/111022; (2004); A1;,
Thiazine – an overview | ScienceDirect Topics
Thiazine | C4H5NS – PubChem

92-30-8, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact.92-30-8,2-(Trifluoromethyl)-10H-phenothiazine, it is a common compound, a new synthetic route is introduced below.

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

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps,and cheap raw materials.154127-42-1,A new synthetic method of this compound is introduced below.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.

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, (S)-4-Hydroxy-2-(3-methoxypropyl)-3,4-dihydro-2H-thieno[3,2-e][1,2]thiazine-6-sulfonamide 1,1-dioxide.

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

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. Methyl 3-oxo-3,4-dihydro-2H-1,4-benzothiazine-6-carboxylate,188614-01-9, This compound has unique chemical properties. The synthetic route is as follows.,188614-01-9

3-QxQ-3, 4-dihydro-2H-benzo [1, 48thiazine-6-carboxylic acid methyl ester (6.74g) was suspended in tetrahydrofuran (lOOmL) and 2M sodium hydroxide (30mL) was added followed by water (20mL). The solution was stirred for 2.5 hours, evaporated to half volume and acidified with 2M hydrochloric acid. The product was collected, washed with water and dried in vacuo, to give a white solid (6.2g). MS (-ve ion electrospray) m/z 208 (M-H)-

While traditionally a conservative industry, chemical producers will need to modernize their PR strategies to stay relevant.we look forward to future research findings about 188614-01-9.

Reference£º
Patent; SMITHKLINE BEECHAM P.L.C.; WO2003/87098; (2003); A1;,
Thiazine – an overview | ScienceDirect Topics
Thiazine | C4H5NS – PubChem

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact.3939-23-9,3-Bromo-10H-phenothiazine, it is a common compound, a new synthetic route is introduced below.3939-23-9

In a nitrogen-flushed 250 mL round-bottom flask with a magnetic stir bar and septum 3-bromo-10H-phenothiazine (4.95 g, 17.8 mmol) was dissolved in dry THF (50 mL) under nitrogen. The colorless solution was deaerated by a constant stream of nitrogen through a syringe for 10 min and cooled to 0 C (ice bath/water). Potassium tert-butanolate (2.40 g, 21.4 mmol) was added to the reaction mixture under nitrogen and the reaction mixture was allowed to come to room temperature and then stirred for 1 h. To this solution 1-bromo hexane (3.00 mL, 21.4 mmol) was slowly added by syringe and stirring at room temp was continued for 16 h. The solvents were removed in vacuo and the residue was adsorbed onto celiteand purified by chromatography on silica gel (n-hexane) to give 5.83 g (90%) of 3-bromo-10-hexyl-10H-phenothiazine (1a) as a yellow resin, Rf (n-hexane) = 0.43. The NMR spectra were in excellent agreement with the literature. 1H NMR (300 MHz, acetone-d6): delta = 0.84 (t, 3J = 7.1 Hz, 3 H), 1.23-1.33 (m, 4 H), 1.44 (dt, 3J = 7.2 Hz, 3J = 6.8 Hz, 2 H), 1.77 (dt, 3J = 7.5 Hz, 3J = 7.5 Hz, 2 H), 3.92 (t, 3J = 7.0 Hz, 2 H), 6.95 (d, 3J = 8.7 Hz, 2 H), 7.03 (dd, 3J = 8.2 Hz, 4J = 0.9 Hz, 1 H), 7.14 (dd, 3J = 7.6 Hz, 4J = 1.4 Hz, 1 H), 7.21 (ddd, 3J = 8.2 Hz, 3J = 7.3 Hz, 4J = 1.6 Hz, 1 H), 7.27 (d, 4J = 2.2 Hz, 1 H), 7.32 (dd, 3J = 8.6 Hz, 4J = 2.3 Hz, 1 H). -13C NMR (75 MHz, acetone-d6): delta = 14.2 (CH3), 23.2 (CH2), 27.0 (CH2), 27.4 (CH2), 32.1 (CH2), 47.9 (CH2), 114.7 (Cquat), 116.9 (CH), 118.1 (CH), 123.6 (CH), 124.7 (Cquat), 128.1 (Cquat), 128.1 (CH), 128.6 (CH), 130.0 (CH), 130.9 (CH), 145.7 (Cquat), 145.9 (Cquat).

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles. 3939-23-9, other downstream synthetic routes, hurry up and to see.

Reference£º
Article; Urselmann, Dominik; Deilhof, Konstantin; Mayer, Bernhard; Mueller, Thomas J. J.; Beilstein Journal of Organic Chemistry; vol. 12; (2016); p. 2055 – 2064;,
Thiazine – an overview | ScienceDirect Topics
Thiazine | C4H5NS – PubChem

154127-42-1, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact.154127-42-1,(S)-4-Hydroxy-2-(3-methoxypropyl)-3,4-dihydro-2H-thieno[3,2-e][1,2]thiazine-6-sulfonamide 1,1-dioxide, it is a common compound, a new synthetic route is introduced below.

Compound B (50.0 g, 140.7 mmol) was added to 450 mL of acetonitrile, trimethyl orthoacetate (27.0 g, 225.1 mmol) and triethylamine (1.4 g, 14.0 mmol) were added with stirring, and the mixture was heated to 78C. , stirring for 5h,HPLC monitoring showed complete reaction and the HPLC monitoring results are shown in Table 1 (see FIG. 1).Cool to 40C, distill off under reduced pressure, and concentrate to a minimum volume.Compound C crude product was obtained.The crude compound C was dissolved in 180 mL of tetrahydrofuran, cooled to -10 DEG C, triethylamine (31.3 g, 309.5 mmol) was slowly added dropwise at a drip rate of 1 d/s, and the addition was completed at a drip rate of 3 d/s. 4- A solution of tosyl chloride (53.5 g, 280.6 mmol) in 70 mL of tetrahydrofuran. After the addition, the temperature was controlled at -4C, and the reaction was complete after about 3 hours.At a controlled temperature of 10 C. or less, a 70% aqueous solution of ethylamine (361.0 g, 5.6 M) was slowly added dropwise at a rate of 5 d/s. After the addition, the temperature was kept stirring at 12C and the reaction was complete after about 15 hours.The mixture was concentrated under reduced pressure to 70-80 mL, and the temperature was lowered to 0C. The temperature was controlled below 30C, and concentrated hydrochloric acid (12 mol/L) was added dropwise to adjust the pH to 1 to 2, and then about 14 mL of concentrated hydrochloric acid (12 mol/L) was added. The mixture was stirred at room temperature for 1 hour. The reaction was extracted twice with methyl tert-butyl ether (2*250 mL). The organic phases were combined and extracted once with dilute hydrochloric acid (1 mol/L, 100 mL). Combine the aqueous phases, slowly add sodium bicarbonate solids, adjust the pH to 5-6, add 150 mL of water, and adjust the pH to 7-8 with 7% sodium bicarbonate solution. After adjustment, stir at room temperature for 15 h and slowly crystallize. After filtration, the filter cake was rinsed with 30 mL of water and the cake was dried to obtain 35.4 g of product with a purity of 98.3%.Add 250 mL of dichloromethane, 25 mL of methanol to the filter mother liquor, stir, extract, separate, and concentrate the organic phase to dryness4.6 g of yellow viscous material was added and 10 mL of ethyl acetate was added. Heat to 70 ~ 75 C dissolved, slowly dropped to 0 ~ 10 C, stirring 1 ~ 2h, precipitation of a white solid, continue stirring 3 ~ 4h, filtration, with 3mL water filter cake, filter cake drying,Obtained product 2.4g, purity 97.3%.Combined, the purity was 98.1%, the total yield was 65.3%, the ignition residue was 0.08%, and the chiral purity was 99.7%.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles. 154127-42-1, other downstream synthetic routes, hurry up and to see.

Reference£º
Patent; Shandong Weizhi Pharmaceutical Co., Ltd.; Shanghai Weizhi Pharmaceutical Technology Co., Ltd.; Wang Jianhua; He Yigang; Wei Yanjun; Xing Yanping; Zhao Tianchang; (27 pag.)CN107759618; (2018); A;,
Thiazine – an overview | ScienceDirect Topics
Thiazine | C4H5NS – PubChem