March 12, 2021 - Heterocyclic Building Blocks-Isothiazole

7716-66-7, 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.,7716-66-7 ,3-Chlorobenzo[d]isothiazole, other downstream synthetic routes, hurry up and to see

It is a common heterocyclic compound, the isothiazole compound, 3-Chlorobenzo[d]isothiazole, cas is 7716-66-7 its synthesis route is as follows.

Preparation Example 20: 3-(4-(Benzo[d]isothiazoI-3-yl)piperazin-l- yl)propan-l-amine dihydrochloride; A mixture of piperazine (10.2 g, 0.118 mmol) and 3-chloro-l ,2- benzisothiazole (4.0 g, 0.024 mmol) in t-BuOH (4 mL) was refluxed overnight. The reaction mixture was poured into water (100 mL) and extracted with toluene (200 mL). The organic phase was dried over MgSO4 and evaporated until about 20 mL remained, under vacuum. The resulting suspension was cooled at 0-5 0C overnight. The precipitate was filtered and dried under vacuum to provide 3-(piperazin- l-yl)benzo[d]isothiazole as an intermediate (3.36 g, 15.4 mmol, 65 percent). MH+ 220A mixture of 3-(piperazin-l-yl)benzo[-i]isothiazole (1.75 g, 8.0 mmol), N-(3-bromopropyl)-phthalimide (1.96 mmol, 7.3 mmol) and K2CO3 (2.21 g, 16.0 mol) in DMF (10 mL) was stirred at 80 0C for 3 hours. The reaction mixture was poured into water (100 mL) and extracted with ethyl acetate (150 mL). The organic phase was dried over MgSO4 and evaporated under vacuum. The residue was further purified by flash column chromatography to provide 2-(3-(4- (benzo[d]isothiazol-3-yl)piperazin-l-yl)propyl)isoindoline-l ,3-dione as an intermediate (1.49 g, 3.67 mmol, 50 percent).To a solution of 2-(3-(4-(benzo[y]isothiazol-3-yl)piperazin-l- yl)propyl)isoindoline- l ,3-dione (1.49 g, 3.67 mmol) in EtOH (25 mL) was added Hydrazine monohydrate (2.5 mL). The mixture was stirred at 80 0C for 1-2 hours and cooled to room temperature. The reaction mixture was poured into water (100 mL) and extracted with DCM (150 mL). The organic phase was dried over MgSO4 and evaporated under vacuum. The residue was redissolved in ether (20-30 mL) and HCl solution (3 mL, 2M in ether) was added to the solution. The resulting precipitate was collected on a filter funnel and dried under vacuum to provide the title compound as HCl salt form (1.1 g, 3.15 mmol, 86 percent).1R NMR (400 MHz, CD3OD3) delta 8.04 (d, J = 8.4 Hz, IH), 7.94 (d, J = 8.0 Hz, IH), 7.55 (t, J = 7.2 Hz, IH), 7.45 (t, J = 7.6 Hz, IH), 4.24- 4.14 (br, 2H), 3.85 (t, J = 7.2 Hz, IH), 3.76-3.66 (br, 2H), 3.59-3.32 (m, 9H), 3.08 (t, J = 7.6 Hz, IH), 2.34-2.30 (m, IH), 2.25-2.17 (m, 2H).MH+ 277

Reference£º
Patent; GREEN CROSS CORPORATION; LEE, Jinhwa; KANG, Suk Youn; PARK, Eun-Jung; SONG, Kwang-Seop; KIM, Min Ju; SEO, Hee Jeong; LEE, Suk Ho; KIM, Jeongmin; PAE, Ae Nim; PARK, Woo-Kyu; WO2010/38948; (2010); A2;,
Isothiazole – Wikipedia
Isothiazole – ScienceDirect.com

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.

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).

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 chemical industry reduces the impact on the environment during synthesis,27148-03-4,Benzo[d]isothiazole-3(2H)-thione 1,1-dioxide,I believe this compound will play a more active role in future production and life.

27148-03-4, 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. Benzo[d]isothiazole-3(2H)-thione 1,1-dioxide, cas is 27148-03-4,the isothiazole compound, it is a common compound, a new synthetic route is introduced below.

The [Zn(tsac)2(o-phen)] complex was prepared by addition of a dissolution of Zn(NO3)26H2O (14.85 mg, 0.049 mmol, 2 ml) into a thiosaccharine solution (20 mg, 0.1 mmol/ethanol:water 1:1,2 ml). A o-phenantroline solution was finally added drop by drop (ethanol:water 1:1, 2 ml) and a yellow power was obtained. The resulting yellow solid was filtered and washed with cold water. Crystals suitable for X-ray diffraction studies were produced by slow diffusion of diethyl ether to the mother solution. Yield: 74% Molar Conductivity (mS M1) = 22.4. Calculated analytical percent composition for C26H16N4O4S4Zn: C = 48.516%; H = 2.267%; N =8.592%; Found: C = 48.638%; H = 2.511%; N = 8.725%. Soluble indimethyl sulfoxide and dimethyl formamide. Non-soluble in other solvents (methanol, chloroform, dichloromethane, acetone, water). UV-Visible [DMSO, kmax nm]: 341. 1HNMR (300 MHz,DMSO) d 8.72-9.21 (m, 1H), 8.94 (m, 1H), 8.31(m, 1H), 8.03-8.21 (m, 1H), 7.91 (m, 1H), 7.57-7.72 (m, 3H). 13CNMR (75 MHz, DMSO) d 191.81 (C1), 149.09 (C8), 140.02 (C10), 139.36(C12), 137.94 (C7), 136.52 (C2), 132.12 (C4), 130.91 (C5), 128.70 (C11), 127.37 (C13), 125.10 (C3), 125.81 (C9), 119.03 (C6).

Reference£º
Article; Delgado, Fermin; Freire, Eleonora; Baggio, Ricardo; Gonzalez Pardo, Veronica; Dorn, Viviana; Dennehy, Mariana; Inorganica Chimica Acta; vol. 479; (2018); p. 266 – 274;,
Isothiazole – Wikipedia
Isothiazole – ScienceDirect.com

PREPARATION 3 3-(1-Piperazinyl)-1,2-benzisothiazole ¡¤ hydrochloride Anhydrous piperazine (49.4 g, 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 funnel. After the flask was purged with nitrogen, it was heated to 100 C. in an oil bath. A solution of 3-chloro-1,2-benzisothiazole (19.45 g, 0.11 mol) in t-butanol (10 mL) was added to the addition funnel, and then slowly added to the reaction flask over 20 minutes to moderate an exothermic reaction (112-118 C.). Once addition was complete the yellow solution was heated to reflux (121 C.) and then maintained at reflux for 24 hours. Thin-layer chromatography showed that the reaction was complete. The reaction mixture was cooled to 85 C. 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 48 C. 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 0 C., granulated for 45 min, and then filtered. The filter cake was washed with cold isopropanol (50 mL) and then dried in vacuo at 40 C. to afford 23.59 g (80% yield) of 3-(1-piperazinyl)-1,2-benzisothiazole hydrochloride as an off white solid.

Reference£º
Patent; Pfizer Inc.; US5935960; (1999); A;,
Isothiazole – Wikipedia
Isothiazole – ScienceDirect.com

10271-85-9, 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.,10271-85-9 ,Isothiazole-5-carboxylic acid, other downstream synthetic routes, hurry up and to see

As a common heterocyclic compound, it belongs to isothiazole compound, name is Isothiazole-5-carboxylic acid, and cas is 10271-85-9, its synthesis route is as follows.

General procedure: The target compounds were synthesized using the procedure given in literature by refluxing aryl/heteroaryl acids with carbohydrazide 4a or 4b in phosphorous oxychloride. The reaction was monitored with the help of TLC to check its completion. After completion of reaction, the mixture was poured over crushed ice and allowed to precipitate. The precipitate was vacuum filtered, dried and recrystallized from methanol. Column chromatography was done on using n-hexane: ethylacetate mixture (7:3). Solvent was evaporated invacuo using rotary evaporator to obtain pure product.

Reference£º
Article; Rane, Rajesh A.; Bangalore, Pavankumar; Borhade, Sheetal D.; Khandare, Preeti K.; European Journal of Medicinal Chemistry; vol. 70; (2013); p. 49 – 58;,
Isothiazole – Wikipedia
Isothiazole – ScienceDirect.com

24340-77-0, 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.,24340-77-0 ,4-Bromoisothiazole, other downstream synthetic routes, hurry up and to see

Name is 4-Bromoisothiazole, as a common heterocyclic compound, it belongs to isothiazole compound, and cas is 24340-77-0, its synthesis route is as follows.

A solution of 5,7-dimethyl-N-(4-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2- yl)phenyl)pyrazolo[l,5-a]pyrimidine-3-carboxamide 6 (286 mg, 0.73 mmol) in DMF (5 mL) was charged with 4-bromoisothiazole (100 mg, 0.60 mmol), potassium acetate (179 mg, 1.8 mmol) and Pd(dppf)Cl2DCM adduct (49 mg, 0.06 mmol) under argon at room temperature. The reaction mixture was heated to 100C for 16 h. The reaction mixture was quenched with water (5 mL), extracted with ethyl acetate (3 X 10 mL) and concentrated under vacuum to obtain crude compound. The crude compound was purified by FCC (eluent, 3-5% methanol in DCM) to afford the title compound as an off-white solid (50 mg, 23%).XH NMR (400 MHz, CDCI3) delta 10.24 (s, 1H), 8.79 (s, 1H), 8.71 (s, 1H), 8.68 (s, 1H), 7.84 (d, J=8.57 Hz, 2H), 7.61 (d, J=8.57 Hz, 2H), 6.78 (s, 1H), 2.83 (s, 3H), 2.74 (s, 3H). ES-MS m/z 350.20 (M+H)+. HPLC purity 99.1%.

Reference£º
Patent; LYSOSOMAL THERAPEUTICS INC.; SKERLJ, Renato, T.; LANSBURY, Peter, T.; GOOD, Andrew, C.; BOURQUE, Elyse, Marie Josee; (139 pag.)WO2016/73895; (2016); A1;,
Isothiazole – Wikipedia
Isothiazole – ScienceDirect.com

87691-88-1, 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.,87691-88-1 ,3-Piperazinobenzisothiazole hydrochloride, other downstream synthetic routes, hurry up and to see

Name is 3-Piperazinobenzisothiazole hydrochloride, as a common heterocyclic compound, it belongs to isothiazole compound, and cas is 87691-88-1, its synthesis route is as follows.

To a solution containing 3- (1-piperazinyl) -1,2_ benzisothiazole hydrochloride (100g) and potassium carbonate (136g) in acetonitrile (800ml) added 1,4_ dibromobutane suspension ( 110g). Vigorous stirring mixture was refluxed for 10 hours, the solvent was distilled off pressure acetonitrile was added water (100ml) and toluene (300ml) to the reaction mixture was distilled net was effected under stirring to break up the product mixture, refluxing under stirring operation , the net after the water addition, cooling down, the suspension was filtered to give a white inorganic salts and organic salts of a mixture of the crude quaternary spiro ammonium base (280g).

Reference£º
Patent; Yantai Besten Pharmaceutical Co., Ltd.; Bi, Haidong; Zhang, Yifang; (8 pag.)CN105669665; (2016); A;,
Isothiazole – Wikipedia
Isothiazole – ScienceDirect.com

Name is 3-Piperazinobenzisothiazole hydrochloride, as a common heterocyclic compound, it belongs to isothiazole compound, and cas is 87691-88-1, its synthesis route is as follows.

To a flask equipped with mechanical stirrer, thermometer, condenser and nitrogen inlet was added 6-cUoro-5-(2-cHoroethyl)-l,3-dihydro-2H-indol-2- one (9.0 g, 39.1 mrnol), 3-(l-pirhoerazinyl)-l,2-benzoisothiazole hydrochloride (10.0 g, 39.1 mmol), sodium carbonate (9.96 g, 117.5 mmol) and poly(ethylene glycol) methyl ether (Mn= 350, 40 mL) and the suspension was heated to 120- 1250C under nitrogen for about 48 hrs. The suspension was cooled and poured into water. The suspension was cooled to 20-250C, the product was collected by filtration on a Buchner funnel and the filter cake was rinsed with water at 20-250C. The damp product was transferred to a flask equipped with mechanical stirrer, 100 mL of water were added and the suspension stirred at ambient temperature for 1 h. The suspension was filtered, washed with water and transferred to a drying oven and dried in vacuo. This afforded 14.2 g (88% yield) of crude ziprasidone.

Reference£º
Patent; APOTEX PHARMACHEM INC.; WO2006/47893; (2006); A1;,
Isothiazole – Wikipedia
Isothiazole – ScienceDirect.com

822-82-2, 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.,822-82-2 ,Isothiazole-4-carboxylic acid, other downstream synthetic routes, hurry up and to see

As a common heterocyclic compound, it belongs to isothiazole compound, name is Isothiazole-4-carboxylic acid, and cas is 822-82-2, its synthesis route is as follows.

A solution of Example 9b (0.19 M in N,N-dimethylacetamide, 237 muL, 0.045 mmol), N,N-diisopropylethylamine (0.21 M in N,N-dimethylacetamide, 262 muL, 0.055 mmol), HATU (0.21 M in N,N-dimethylacetamide, 238 muL, 0.05 mmol), and isothiazole-4-carboxylic acid (0.4M in N,N-dimethylacetamide, 125 muL, 0.05 mmol) were aspirated from their respective source vials, mixed through a perfluoroalkoxy alkanes mixing tube (0.2 mm inner diameter), and loaded into an injection loop. The reaction segment was injected into the flow reactor (Hastelloy coil, 0.75 mm inner diameter, 1.8 mL internal volume) set at 100 C., and passed through the reactor at 180 muL min-1 (10 minute residence time). Upon exiting the reactor, the reaction was loaded directly into an injection loop and purified using preparative HPLC to yield the title compound (9.95 mg, 49.50% yield). Samples were purified by preparative HPLC on a Phenomenex Luna C8 (2) 5 mum 100 AXIA column (50 mm¡Á21.2 mm). A gradient of acetonitrile (A) and 0.1% trifluoroacetic acid in water (B) was used, at a flow rate of 30 mL/min (0-0.5 minutes 5% A, 0.5-6.5 minutes linear gradient 5-60% A, 6.5-7.0 minutes linear gradient 60-100% A, 7.0-8.9 minutes 100% A, 8.9-9.0 minutes linear gradient 100-5% A, 9.0-10 minutes 5% A). A sample volume of 1.0 mL was injected directly from the flow reactor stream to the HPLC system. A custom purification system was used, consisting of the following modules: Gilson 305 and 306 pumps; Gilson 806 Manometric module; Gilson UV/Vis 155 detector; Gilson 506C interface box; Gilson FC204 fraction collector; Agilent G1968D Active Splitter; Thermo MSQ Plus mass spectrometer. The system was controlled through a combination of Thermo Xcalibur 2.0.7 software and a custom application written in-house using Microsoft Visual Basic 6.0. 1H NMR (400 MHz, DMSO-d6) delta 4.69 (d, J=3.9 Hz, 2H), 5.62 (s, 2H), 6.43 (s, 1H), 6.84 (d, J=2.0 Hz, 1H), 7.51 (d, J=2.0 Hz, 1H), 8.18 (s, 1H), 8.32 (s, 1H), 8.96 (s, 1H), 9.59 (s, 1H). MS (APCI) m/z 439.1 [M+H]+.

Reference£º
Patent; AbbVie Inc.; Dai, Yujia; McClellan, William; Michaelides, Mike; Sweis, Ramzi; Wilson, Noel; Dietrich, Justin; (90 pag.)US2017/174688; (2017); A1;,
Isothiazole – Wikipedia
Isothiazole – ScienceDirect.com

936-16-3, 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.,936-16-3 ,2,3-Dihydrobenzo[d]isothiazole 1,1-dioxide, other downstream synthetic routes, hurry up and to see

Name is 2,3-Dihydrobenzo[d]isothiazole 1,1-dioxide, as a common heterocyclic compound, it belongs to isothiazole compound, and cas is 936-16-3, its synthesis route is as follows.

Ethyl chloroformate (136ml) was added dropwise to a chilled solution of 2,3-dihydro- 1,2-benzisothiazol-1 ,1 -dioxide (68.Og) in pyridine (340ml) over 1h, maintaining the temperature below 180C. The slurry was stirred for 10min at 2O0C, diluted dropwise with water (1000ml) over 75min and stirred for a further 30min. The mixture was chilled to 0-50C, aged for 1 h and isolated by filtration. The cake was washed with cold water (2x250ml), and dried in vacuo to give the title compound as a white solid (72.35g).400 MHz NMR in dimethyl sulphoxide-d6. Dimethyl sulphoxide-d5 as reference at 2.50 ppm. delta (ppm): 1.30 (3) t J=7.1Hz, 4.32 (2H) q J=7.1Hz, 5.01 (2H) s, 7.64-7.70 (2H) m, 7.81 (1 H) td J=7.6Hz J=1.0Hz, 7.98 (1 H) d J=8.0Hz

Reference£º
Patent; GLAXO GROUP LIMITED; WO2006/129100; (2006); A1;,
Isothiazole – Wikipedia
Isothiazole – ScienceDirect.com