Day: August 26, 2020

A common heterocyclic compound, the thiazines compound, name is 3,4-Dihydro-2H-benzo[b][1,4]thiazine,cas is 3080-99-7, mainly used in chemical industry, its synthesis route is as follows.

In a manner similar to the method described in Example 1-1, using 3,4-dihydro-2H-benzo[1,4]thiazine in place of 1,2,3,4-tetrahydroquinoline, 239 mg (yield: 63%) of the captioned compound was obtained.1H-NMR (ppm) (300 MHz, CDCl3) 6.98 (1H, dd, J = 1.8, 7.9 Hz), 6.86 (1H, ddd, J = 1.8, 7.3, 8.5 Hz), 6.78 (1H, d, J = 8.2 Hz), 6.69-6.65 (2H, m), 6.61-6.5 (1H, ddd, J = 1.2, 7.6, 8.5 Hz), 4.61 (1H, d, J = 8.2 Hz), 3.85 (3H, s), 3.60-3.51 (3H, m), 3.14-2.96 (4H, m), 2.55-2.50 (1H, m), 2.41 (3H, s), 2.38-2.32 (1H, m), 2.23-2.12 (2H, m), 1.91-1.47 (5H, m), 1.12-1.00 (1H, m) IR (cm-1) (KBr) 2924, 1735, 1606, 1584, 1483, 1438, 1373, 1338, 1275, 1257, 1176, 1148, 1112, 1079, 1047, 1006, 937, 907, 891, 854, 793, 744

As the rapid development of chemical substances, we look forward to future research findings about 3080-99-7

Reference£º
Patent; TORAY INDUSTRIES, INC.; EP1555266; (2005); A1;,
Thiazine – an overview | ScienceDirect Topics
Thiazine | C4H5NS – PubChem

A common heterocyclic compound, the thiazines compound, name is 1,2-Thiazinane 1,1-dioxide,cas is 37441-50-2, mainly used in chemical industry, its synthesis route is as follows.

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).

As the rapid development of chemical substances, we look forward to future research findings about 37441-50-2

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

A common heterocyclic compound, the thiazines compound, name is Methyl 4-hydroxy-2H-thieno[2,3-e][1,2]thiazine-3-carboxylate 1,1-dioxide,cas is 98827-44-2, mainly used in chemical industry, its synthesis route is as follows.

EXAMPLE 6 A solution of 4-hydroxy-3-methoxycarbonyl-2H-thieno-[2,3-e]-1,2-thiazine 1,1-dioxide (0.7 g) and 2-aminotropone (0.341 g) in xylene (7 ml) was refluxed for 21 hours and the reaction mixture was allowed to stand at ambient temperature. The crystalline precipitates were collected by filtration, washed with toluene and recrystallized from tetrahydrofuran to give 4-hydroxy-N-(1-oxo-2,4,6cycloheptatrien-2-yl)-2H-thieno[2,3-e]-1,2-thiazine-3-carboxamide 1,1-dioxide (0.47 g). mp: 230 C. (dec.). IR (Nujol): 3260, 1550, 1500, 1450, 1400, 1340, 1180 cm-1 NMR (DMSO-d6, delta): 7.00-7.47 (5H, m), 7.57 (1H, d, J=5 Hz), 8.17 (1H, d, J=5 Hz), 8.89 (1H, d, J=9 Hz), 10.53 (1H, brs).

As the rapid development of chemical substances, we look forward to future research findings about 98827-44-2

Reference£º
Patent; Fujisawa Pharmaceutical Co., Ltd.; US4563453; (1986); A;,
Thiazine – an overview | ScienceDirect Topics
Thiazine | C4H5NS – PubChem

A common heterocyclic compound, the thiazines compound, name is 1,2-Thiazinane 1,1-dioxide,cas is 37441-50-2, mainly used in chemical industry, its synthesis route is as follows.

To a mixture of 2,4-difluorobenzonitrile (10.0 g, 72 mmol) and 1,1-dioxo-1lambda6-[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) delta 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.

As the rapid development of chemical substances, we look forward to future research findings about 37441-50-2

Reference£º
Patent; Bristol-Myers Squibb Company; US2007/111984; (2007); A1;,
Thiazine – an overview | ScienceDirect Topics
Thiazine | C4H5NS – PubChem

A common heterocyclic compound, the thiazines compound, name is 1,2-Thiazinane 1,1-dioxide,cas is 37441-50-2, mainly used in chemical industry, its synthesis route is as follows.

solution of 2-(3-chloro-4-fluorobenzyl)-8-ethyl-4-fluoro-10-methoxy-6-methyl-7,8- dihydropyrazino[l’,2′: 1,5]pyrrolo[2,3-d]pyridazine-1,9(2H,6H)-dione (0.10 g, 0.23 mmol; Example 139), 1,2-thiazinane 1,1-dioxide (45 mg, 0.33 mmol), and cesium carbonate (0.15 g, 0.46 mmol) in anhydrous DMSO (9.5 mL) was heated in an oil bath at 50 C for 5 hours. The product mixture was filtered through a pad of Celite and the filtrate was subjected to purification on reverse phase preparative HPLC purification. Collection and lyophilization of appropriate fractions afforded the title material. Analytical HPLC indicated that the product is a 1:1 mixture of two isomers that arose from the relative stereochemistry of the 6-methyl group and restricted rotation between the sultam ring and the tricyclic core. ?H NMR (400 MHz, CDCI3) No. 7.48 (m 1H), 7.28 (m, 1H), 7.11 (t, J = 8.5 Hz, 1H), 5.17 (d, J = 14.2 Hz, ?H), 5.34 (in, 1/2 H), 5.29 (d, J = 14.2 Hz, (at)H), 5.23 (d, J = 14.2 Hz, ?H), 5.09 (d, J = 14.2 Hz, ?H), 5.07 (m, ?H), 4.18 (s, 1.5H), 4.16 (s, 1.5H), 4.12-3.17 (m), 2.58-2.00 (m), 1.57 (d, J = 6.6 Hz, 1.5H), 1.42 (d, J = 6.8 Hz, 1.5H), 1.23 (t, J = 6.8 Hz, 1.5H), 1.22 (t, J = 7.1 Hz, 1.5H). ES MS M+1 = 552

As the rapid development of chemical substances, we look forward to future research findings about 37441-50-2

Reference£º
Patent; MERCK & CO., INC.; WO2005/110414; (2005); A2;,
Thiazine – an overview | ScienceDirect Topics
Thiazine | C4H5NS – PubChem

A common heterocyclic compound, the thiazines compound, name is (S)-4-Hydroxy-2-(3-methoxypropyl)-3,4-dihydro-2H-thieno[3,2-e][1,2]thiazine-6-sulfonamide 1,1-dioxide,cas is 154127-42-1, mainly used in chemical industry, its synthesis route is as follows.

Prepare a 1L three-vial bottle equipped with a mechanical stirrer, a constant pressure low liquid funnel, and an ice water bath.Add compound of formula A (100 g, 0.28 mol) and acetonitrile (400 mL),Under N2 protection, stirring and cooling to 5 ~ 10 C,Then drop itTrimethyl orthoacetate(77.3g, 0.64mol),The rate of addition is such that the stability of the system does not exceed 15C.After the addition, remove the cooling and continue the reaction for 1 hour.TLC detected the disappearance of the starting material, creating a slightly more polar new point.Concentrate at normal pressure, recover the solvent and add the residue to DCM.Swirling to replace desolvation, and finally high vacuum drying for 1 hour,The residue is a compound of formula B-1Can be directly used in subsequent reactions without purificationThe reaction gave the crude product B-1 in equivalent yield.

As the rapid development of chemical substances, we look forward to future research findings about 154127-42-1

Reference£º
Patent; Shanghai Bo Shirui Life Technology Co., Ltd.; Wang Dong; Wang Fangdao; Wang Meng; Cai Maojun; (16 pag.)CN107722043; (2018); A;,
Thiazine – an overview | ScienceDirect Topics
Thiazine | C4H5NS – PubChem

A common heterocyclic compound, the thiazines compound, name is 2-Cyano-phenothiazine,cas is 38642-74-9, mainly used in chemical industry, its synthesis route is as follows.

2-cyanophenothiazine (0.74 g, 3.30 mmol) was dissolved in 10 mL of anhydrous DMF. The mixture was cooled to 0 C and 60 % NaH (0.40 g, 9.90 mmol) was added. The dark mixture was stirred at 0 C for an additional 15 mm and Di-tert-butyl dicarbonate (0.90 g, 3.96 mmol) was added. The mixture was stirred at room temperature for 3 h and was diluted with 50 mL of brine. The aqueous layer was extracted with three 25 mL portions of ethyl acetate. The combined organic extract was dried over anhydrous MgSO4 and concentrated under diminished pressure. The crude was purified on a silica gel column (10 cm x 2 cm). Elution with ethyl acetate-hexane (1:9) gave 1 as a pale yellow solid: yield 1.07 g (100%); silica gel TLC R10.26 (ethyl acetate-hexane 1:9); ?HNIVIR (CDC13) 51.49 (s, 9H), 7.16-7.20 (m, 1H), 7.28-7.33 (m, 2H), 7.40 (s, 2H), 7.49 (d, 1H, J= 8.4 Hz) and 7.80 (s, 1H); ?3CI?IvIR 28.1, 83.1, 110.2, 118.2, 126.6, 127.2, 127.3, 127.5, 128.1,129.1, 130.3, 130.6, 137.7, 139.0, 139.1 and 151.8; mass spectrum (APCI), m/z 325.1017 (M+H) (C18H17N202S requires m/z 325.1011).

As the rapid development of chemical substances, we look forward to future research findings about 38642-74-9

Reference£º
Patent; ARIZONA BOARD OF REGENTS ON BEHALF OF ARIZONA STATE UNIVERSITY; HECHT, Sidney; KHDOUR, Omar; CHOWDHURY, Sandipan, Roy; BANDYOPADHAY, Indrajit; (85 pag.)WO2016/133995; (2016); A1;,
Thiazine – an overview | ScienceDirect Topics
Thiazine | C4H5NS – PubChem

The thiazines compound, cas is 92-39-7 name is 2-Chloro-10H-phenothiazine, mainly used in chemical industry, its synthesis route is as follows.

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

With the rapid development of chemical substances, we look forward to future research findings about 92-39-7

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

2-Methoxyphenothiazine, cas is 1771-18-2, it is a common heterocyclic compound, the thiazines compound, its synthesis route is as follows.

EXAMPLE 5 Reaction of 5-methyl-2-pyrrolidinone, 2-methoxyphenothiazine and phosphorus oxychloride in 1,2-dichloroethane according to the procedure of Example 4 affords 2-METHOXY-10-[5-METHYL-1-(5-METHYL-1-PYRROLIN-2-YL)-2-PYRROLIN-2-YL]PHENOTHIAZINE HYDROCHLORIDE (8.6% yield), m.p. 236.5-238.5 C. (corr.), from ethanol-ether.

With the rapid development of chemical substances, we look forward to future research findings about 1771-18-2

Reference£º
Patent; Mead Johnson & Company; US3946004; (1976); A;,
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.

3-Oxo-3, 4-dihydro-2H-benzo [1, 4] thiazine-6-carboxylic acid methyl ester (6.74 g) was suspended in tetrahydrofuran (100 ml) and 2M sodium hydroxide [(30] ml) was added followed by water (20 ml). 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 (6.2 g). MS (-ve ion electrospray) [L} L/Z] 208 (M-H)-

With the rapid development of chemical substances, we look forward to future research findings about 188614-01-9

Reference£º
Patent; GLAXO GROUP LIMITED; WO2004/2992; (2004); A1;,
Thiazine – an overview | ScienceDirect Topics
Thiazine | C4H5NS – PubChem