Analyzing the synthesis route of 3-Chlorobenzo[d]isothiazole

With the synthetic route has been constantly updated, we look forward to future research findings about 3-Chlorobenzo[d]isothiazole,belong isothiazole compound

As a common heterocyclic compound, it belong isothiazole compound,3-Chlorobenzo[d]isothiazole,7716-66-7,Molecular formula: C7H4ClNS,mainly used in chemical industry, its synthesis route is as follows.,7716-66-7

EXAMPLE B4 A mixture of 3,4-dihydro-7-methoxybenzofuro[2,3-c]pyridine-2(1H)-butanamine (0.0055 mol), 3-chloro-1,2-benzisothiazole (0.0089 mol) and NaHCO3 (0.01 mol) was stirred for 1.5 hour at 120¡ã C. (melt). 1-Butanol (0.5 ml) was added. The reaction mixture was cooled, then dissolved in CH2Cl2 and purified by column chromatography over silica gel (eluent: CH2Cl2/(CH3OH/NH3) 98/2). The desired fractions were collected and the solvent was evaporated. The residue was dissolved in 2-propanone and converted into the hydrochloric acid salt (1:2) with HCl/2-propanol. The mixture was stirred at room temperature. The precipitate was filtered off and dried, yielding 1.60 g of N-(1,2-benzisothiazol-3-yl)-3,4-dihydro-7-methoxybenzofuro[2,3-c]pyridine-2(1H)-butanamine monohydrochloride monohydrate (61percent) (compound 55).

With the synthetic route has been constantly updated, we look forward to future research findings about 3-Chlorobenzo[d]isothiazole,belong isothiazole compound

Reference£º
Patent; Janssen Pharmaceutica N.V.; US6495555; (2002); B1;,
Isothiazole – Wikipedia
Isothiazole – ScienceDirect.com

 

The important role of 7716-66-7

With the complex challenges of chemical substances, we look forward to future research findings about 3-Chlorobenzo[d]isothiazole

Name is 3-Chlorobenzo[d]isothiazole, as a common heterocyclic compound, it belongs to isothiazole compound, and cas is 7716-66-7, its synthesis route is as follows.,7716-66-7

Preparation 3 3-(1-Piperazinyl)-1,2-benzisothiazole ¡¤ hydrochloride Anhydrous piperazine (49.4g, 0.57 mol) and t-butanol (10 mL) were added to a dry, 300 mL round bottom flask equipped with a mechanical stirrer, thermometer, condenser topped with a nitrogen inlet, and pressure-equalizing dropping tunnel. After the flask was purged with nitrogen, it was heated to 100C in an oil bath. A solution of 3-chloro-1,2-benzisothiazole (19.45g, 0.11 mol) in t-butanol (10 mL) was added to the addition tunnel, and then slowly added to the reaction flask over 20 minutes to moderate an exothermic reaction (112 – 118C). Once addition was complete the yellow solution was heated to reflux (121C) and then maintained at reflux for 24 hours. Thin-layer chromatography showed that the reaction was complete. The reaction mixture was cooled to 85C and 120 mL of water was added. The hazy solution was filtered and the filter cake rinsed with 60 mL of t-butanol/water (1:1) solution. The pH of the combined filtrate and wash was adjusted to 12.2 with 50% aqueous caustic. The aqueous solution was extracted with toluene (200 mL), the layers were separated, and the aqueous layer was extracted with fresh toluene (100 mL). The combined toluene layers were washed with water (75 mL), and then the toluene solution was concentrated in vacuo at 48C to 90 mL. Isopropanol (210 mL) was added to the concentrate and then the pH was slowly adjusted to 3.8 with 7.6 mL of concentrated hydrochloric acid. The resulting slurry was cooled to 0C, granulated for 45 min, and then filtered. The filter cake was washed with cold isopropanol (50 mL) and then dried in vacuo at 40C to afford 23.59g (80% yield) of 3-(1-piperazinyl)-1,2-benzisothiazole hydrochloride as an off white solid.

With the complex challenges of chemical substances, we look forward to future research findings about 3-Chlorobenzo[d]isothiazole

Reference£º
Patent; PFIZER INC.; EP790236; (1997); A1;,
Isothiazole – Wikipedia
Isothiazole – ScienceDirect.com

 

Downstream synthetic route of 3-Chlorobenzo[d]isothiazole

With the complex challenges of chemical substances, we look forward to future research findings about 3-Chlorobenzo[d]isothiazole,belong isothiazole compound

As a common heterocyclic compound, it belongs to quinuclidine compound,Quinuclidine-4-carboxylic acid hydrochloride,40117-63-3,Molecular formula: C8H14ClNO223,mainly used in chemical industry, its synthesis route is as follows.,7716-66-7

3-Chloro-1 ,2-benzisothiazole (147 mg, 0.87 mmol) was added to a solution of the piperidine of preparation 60 (200 mg, 0.72 mmol) in acetonitrile (20 mi). 1 ,8-Diazabicyclo[5.4.0]undec-7-ene (111 mul, 0.72 mmol) was added, and the reaction mixture was then stirred at room temperature for 48 hours. It was then concentrated under reduced pressure and the crude product was purified by EPO column chromatography on silica gel using dichloromethane/methanol/aqueous ammonia as eluant (90:10:1 v/v/v) to yield the title compound (290 mg, 98percent) as a solid.1H NMR (400MHz, CD3OD): delta 1.80-1.85 (m, 2H), 2.00-2.10 (m, 2H), 2.23 (s, 3H), 2.57 (m, 1 H), 2.85-2.91 (m, 2H), 3.23-3.28 (m, 2H), 7.32 (t, 1 H), 7.43 (d, 2H), 7.61-7.68 (m, 4H), 7.74 (d, 1 H); LRMS APCI+ m/z 410 [MH]+.

With the complex challenges of chemical substances, we look forward to future research findings about 3-Chlorobenzo[d]isothiazole,belong isothiazole compound

Reference£º
Patent; PFIZER LIMITED; WO2006/114706; (2006); A1;,
Isothiazole – Wikipedia
Isothiazole – ScienceDirect.com

 

The important role of 7716-66-7

With the complex challenges of chemical substances, we look forward to future research findings about 3-Chlorobenzo[d]isothiazole

Name is 3-Chlorobenzo[d]isothiazole, as a common heterocyclic compound, it belongs to isothiazole compound, and cas is 7716-66-7, its synthesis route is as follows.,7716-66-7

To a solution of 3-chlorobenzo[d]isothiazole (0.5 00 g, 2.941 mmol) in sulphuric acid (5 mL) was added potassium nitrate (272 mg, 2.69 mmol) portion wise at 0-5¡ãC. The reaction mass was stirred at rt for 12 h. The reaction mass was quenched with water and the precipitate obtained was filtered. The precipitate was purified by column chromatography to afford 220 mg of the title product. 1H NMR (300 MHz, CDC13): delta 8.59 (d, J = 7.8 Hz, 1H), 8.40 (d, J = 7.8 Hz, 1H), 7.76 (t, / = 7.8 Hz, 1H).

With the complex challenges of chemical substances, we look forward to future research findings about 3-Chlorobenzo[d]isothiazole

Reference£º
Patent; GLENMARK PHARMACEUTICALS S.A.; GHARAT, Laxmikant Atmaram; BANERJEE, Abhisek; PAWAR, Mahesh Yashwant; KHAIRATKAR-JOSHI, Neelima; KATTIGE, Vidya Ganapati; WO2013/38308; (2013); A1;,
Isothiazole – Wikipedia
Isothiazole – ScienceDirect.com

 

The important role of 7716-66-7

With the complex challenges of chemical substances, we look forward to future research findings about 3-Chlorobenzo[d]isothiazole

Name is 3-Chlorobenzo[d]isothiazole, as a common heterocyclic compound, it belongs to isothiazole compound, and cas is 7716-66-7, its synthesis route is as follows.,7716-66-7

Ethylenediamine (45 mL) was heated to 80 0C. A room temperature solution of 3-chlorobenzo[d]isothiazole (12g, 70.7 mmol) in ethylenediamine (5 mL) was added to the heated ethylenediamine dropwise. The resulting solution was heated at 80 0C for 3 h. The reaction mixture was cooled to room temperature and water (75 mL) was added. The aqueous mixture was extracted with ethyl acetate twice and the ethyl acetate layers were separated. The combined organic layers were dried over anhydrous sodium sulfate, filtered and the filtrate concentrated under reduced pressure to yield N1-(benzo[d]isothiazol-3-yl)ethane-l,2-diamine as a light yellow solid (8 g). 1H-NMR (300 MHz, CDCl3): 7.79-7.64 (m, 2H), 7.52 (t, IH), 7.34 (t, IH), 5.60 (broad s, IH), 3.62 (t, 2H), 3.08 ppm (t, 2H).

With the complex challenges of chemical substances, we look forward to future research findings about 3-Chlorobenzo[d]isothiazole

Reference£º
Patent; RIGEL PHARMACEUTICALS, INC.; WO2006/91858; (2006); A1;,
Isothiazole – Wikipedia
Isothiazole – ScienceDirect.com

 

Extracurricular laboratory: Synthetic route of 7716-66-7

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 reaction routes of 3-Chlorobenzo[d]isothiazole, 7716-66-7

7716-66-7, 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. 3-Chlorobenzo[d]isothiazole, cas is 7716-66-7,the isothiazole compound, it is a common compound, a new synthetic route is introduced below.

An eggplant type flask was charged with 3-chloro(1,2-benzisothiazole) (14 g, 200 mmol) and piperazine anhydride (6.8 g, 40 mmol) and heated at 125 ¡ã C. for 24 hours. After completion of the reaction, 52 ml of ice- In addition, quench, add 3.2 g of 50percent NaOH solution, stir for 5 min, extract with CH 2 Cl 2 50 ml * 3, wash the organic layer with 50 ml each of ice water * 2, 50 ml * 2 of saturated brine * 2 and anhydrous MgSO4 To give 4- (1,2-benzisothiazol-3-yl)piperazine.

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 reaction routes of 3-Chlorobenzo[d]isothiazole, 7716-66-7

Reference£º
Patent; JIANGSU HENGYI PHARMACEUTICAL COMPANY LIMITED; SHANGHAI INSTITUTE OF PHARMACEUTICAL INDUSTRY; Li, JIANQI; PENG, SHAOPING; CAI, WANGPING; GAO, KAI; (39 pag.)JP5714152; (2015); B2;,
Isothiazole – Wikipedia
Isothiazole – ScienceDirect.com

 

Some tips on 3-Chlorobenzo[d]isothiazole

With the complex challenges of chemical substances, we look forward to future research findings about 7716-66-7,belong isothiazole compound

As a common heterocyclic compound, it belongs to isothiazole compound, name is 3-Chlorobenzo[d]isothiazole, and cas is 7716-66-7, its synthesis route is as follows.,7716-66-7

Synthesis of 5-Bromo-3-chlorobenzo[d]isothiazole. 3-Chlorobenzo[d]isothiazole (10 g, 59.0 mmol) was added to a solution of bromine (3.2 mL, 62.0 mmol) and silver sulfate (19.6 g, 63.0 mmol) in sulfuric acid (200 mL). The resulting brown mixture was allowed to stir at room temperature for 2h under nitrogen. The color slowly faded to pale yellow as a white precipitate formed. The precipitate was collected by vacuum filtration and triturated with hexanes to yield 5-bromo-3-chlorobenzo[d]isothiazole as a white solid (3.8 g). 1H NMR (300 MHz, CDCl3): 8.18 (s, IH), 7.8 (d, IH), 7.64 ppm (d, IH).; 3-Chlorobenzo[d]isothiazole (10 g, 59.0 mmol) was added to a solution of bromine (3.2 mL, 62.0 mmol) and silver sulfate (19.6 g, 63.0 mmol) in sulfuric acid (200 mL). The resulting brown mixture was allowed to stir at room temperature for 2h under nitrogen. The color slowly faded to pale yellow as a white precipitate formed. The precipitate was collected by vacuum filtration and triturated with hexanes to yield 5-bromo-3-chlorobenzo[d]isothiazole as a white solid (3.8 g). 1H NMR (300 MHz, CDCl3): 8.18 (s, IH), 7.8 (d, IH), 7.64 ppm (d, IH).

With the complex challenges of chemical substances, we look forward to future research findings about 7716-66-7,belong isothiazole compound

Reference£º
Patent; RIGEL PHARMACEUTICALS, INC.; WO2006/91858; (2006); A1;,
Isothiazole – Wikipedia
Isothiazole – ScienceDirect.com

 

The important role of 7716-66-7

With the complex challenges of chemical substances, we look forward to future research findings about 3-Chlorobenzo[d]isothiazole

Name is 3-Chlorobenzo[d]isothiazole, as a common heterocyclic compound, it belongs to isothiazole compound, and cas is 7716-66-7, its synthesis route is as follows.,7716-66-7

General procedure for synthesis of 3-(piperazin-1-yl)benzo[d]isothiazole The compound 3-chloro-1, 2-benzisothiazole (1 mmol) was allowed to react with piperazine (1.2 mmol) in Ethanol at 80 ¡ãC for 36 h. Then reaction mixture was concentrate and RM was dissolved in ethyl acetate and washed with water. Ethylacetate layer dried with Na2SO4 and concentrate them and get 3-(piperazin-1-yl)benzo[d]isothiazole. White solid, 85percent yield, mp 215-217 ¡ãC, 1H NMR (400 MHz, CDCl3): delta = 7.42 (t, J = 7.2 Hz, 1H), 7.29 (m, 3H), 4.14 (t, J = 4.8 Hz, 4H), 3.15 (t, J = 4.8 Hz, 4H); 13C NMR (100 MHz, DMSO+CDCl3): 166.8, 156.2, 135.8, 128.5, 127.6, 125.2, 124.9, 119.8, 53.6, 49.2, 46.6, 45.1, 7.1. MS calcd for C19H20N4OS2: 219.31. Found: 220.33, (M+); Anal. Calcd for C19H20N4OS2: C, 60.24; H, 5.97; N, 19.16; S, 14.62; Found: C, 60.25; H, 5.99; N, 19.13; S, 14.61.

With the complex challenges of chemical substances, we look forward to future research findings about 3-Chlorobenzo[d]isothiazole

Reference£º
Article; Reddy, Kummetha Indrasena; Srihari, Konduri; Renuka, Janupally; Sree, Komanduri Shruthi; Chuppala, Aruna; Jeankumar, Variam Ullas; Sridevi, Jonnalagadda Padma; Babu, Kondra Sudhakar; Yogeeswari, Perumal; Sriram, Dharmarajan; Bioorganic and Medicinal Chemistry; vol. 22; 23; (2014); p. 6552 – 6563;,
Isothiazole – Wikipedia
Isothiazole – ScienceDirect.com

 

Some tips on 3-Chlorobenzo[d]isothiazole

With the complex challenges of chemical substances, we look forward to future research findings about 7716-66-7,belong isothiazole compound

As a common heterocyclic compound, it belongs to isothiazole compound, name is 3-Chlorobenzo[d]isothiazole, and cas is 7716-66-7, its synthesis route is as follows.,7716-66-7

(a) A mixture of 32 parts of ethyl 1-piperazinecarboxylate, 17 parts of 3-chloro-1,2-benzisothiazole and 45 parts of N,N-dimethylacetamide was stirred for 0.5 hours at 150¡ã C. After cooling to 50¡ã C., the reaction mixture was poured into ice water. The aqueous layer was decanted and the oily layer was stirred in water. The product from the oil layer was extracted with trichloromethane. The extract was dried, filtered and evaporated. The residue was purified by column chromatography over silica gel using a mixture of trichloromethane and methanol (95:5 by volume) as eluent. The pure fractions were collected and the eluent was evaporated, yielding 13 parts (44percent) of ethyl 4-(1,2-benzisothiazol-3-yl)-1-piperazinecarboxylate as a residue (int. 3).

With the complex challenges of chemical substances, we look forward to future research findings about 7716-66-7,belong isothiazole compound

Reference£º
Patent; Janssen Pharmaceutica N.V.; US4957916; (1990); A;,
Isothiazole – Wikipedia
Isothiazole – ScienceDirect.com

 

Some tips on 3-Chlorobenzo[d]isothiazole

With the complex challenges of chemical substances, we look forward to future research findings about 7716-66-7,belong isothiazole compound

As a common heterocyclic compound, it belongs to isothiazole compound, name is 3-Chlorobenzo[d]isothiazole, and cas is 7716-66-7, its synthesis route is as follows.,7716-66-7

A solution of 3-(4-(4-fluorophenyl)-1-piperidyl)-1-propanol (10 g) in dry toluene (150 ml) was treated portionwise with a 50percent xylene suspension of sodium hydride (3 g). A solution of 3-chloro-1,2-benzisothiazole (3.6 g) in dry toluene (30 ml) was added dropwise at room temperature followed by stirring for 1.5 h at room temperature. Ice was added, the phases separated and the aqueous phase extracted with ether. Drying of the combined organic phases over magnesium sulfate and removal of solvents in vacuo gave an oil which was applied to column chromatography (silica gel, eluent:ethyl acetate/heptane/triethyl amine=50:50:4). The title compound 21 crystallized from a mixture of isopropyl ether/heptane. Yield: 1.5 g, mp: 91¡ã-92¡ã C.

With the complex challenges of chemical substances, we look forward to future research findings about 7716-66-7,belong isothiazole compound

Reference£º
Patent; Lundbeck; H.; US5665725; (1997); A;,
Isothiazole – Wikipedia
Isothiazole – ScienceDirect.com