6609-54-7

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A solution of 2-(methylthio)benzonitrile (29.8 g) in dry ether (150 ml ) was added dropwise to a stirred suspension of lithium aluminium hydride (11.6 g) in dry ether (360 ml) under nitrogen. A thick gum formed which was dissolved by the addition of dry THF (100 ml). The mixture was stirred at room temperature for 2 hours, Water (12 ml) was then carefully added followed by a 15% aqueous solution of sodium hydroxide (36 ml) and more water (12 ml). The mixture, was filtered, the filtrate washed with water, dried and evaporated in vacuo. The residue was distilled in vacuo to give a colourless oil. Yield=20.9 g. A thick gum formed which The mixture, was filtered the filtrate washed with water dried evaporated in vacuo The residue was distilled in vacuo to give a colourless oil

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a 500 ml four-necked flask equipped with a stirrer, a thermometer, and a condenser, 29.8 g (0.2 mol) of 2-(methylthio)benzonitrile, 100 g of monochlorobenzene, and 4.32 g (0.24 mol) of water were added. To the flask, 29.7 g (0.22 mol) of sulfuryl chloride was added with stirring at a temperature of from 5° to 15° C., heated to a temperature of from 70° to 80° C., and allowed to react for 1 hour. After the completion of the reaction, the reaction mixture was cooled to room temperature to precipitate white crystals. The white crystals were washed with monochlorobenzene, and dried to give 29.0 g of 1,2-benzisothiazol-3-one (melting point: 157° to 158° C.). The yield of the product was 96% against the starting 2-(methylthio)benzonitrile. To a 500 ml four-necked flask equipped with a stirrer heated to a temperature of from 70° to 80° C. to react for 1 hour After the completion of the reaction to precipitate white crystals The white crystals were washed with monochlorobenzene dried

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A solution of 2-(methylthio)benzonitrile (29.8 g) in dry ether (150 ml ) was added dropwise to a stirred suspension of lithium aluminium hydride (11.6 g) in dry ether (360 ml) under nitrogen. A thick gum formed which was dissolved by the addition of dry THF (100 ml). The mixture was stirred at room temperature for 2 hours, Water (12 ml) was then carefully added followed by a 15% aqueous solution of sodium hydroxide (36 ml) and more water (12 ml). The mixture, was filtered, the filtrate washed with water, dried and evaporated in vacuo. The residue was distilled in vacuo to give a colourless oil. Yield=20.9 g. A thick gum formed which The mixture, was filtered the filtrate washed with water dried evaporated in vacuo The residue was distilled in vacuo to give a colourless oil

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 2-Chlorobenzonitrile (27.5 g, 0.2 mol), monochlorobenzene (30.0 g), and a 50% by weight aqueous solution (1.0 g) of tetra-n-butyl ammonium bromide were placed in a 500-ml four-necked flask equipped with a stirrer, a thermometer, a dropping funnel, and a condenser under a nitrogen atmosphere to obtain a mixture. A 30% by weight aqueous solution (51.4 g) of sodium salt of methanethiol (0.22 mol) was added dropwise to the mixture at 60 to 65° C. over a period of 5 hours under stirring. After completion of the dropwise addition, the mixture was further allowed to react at the same temperature for 12 hours. By this operation, 2-(methylthio)benzonitrile was obtained. equipped with a stirrer a thermometer, a dropping funnel, and a condenser under a nitrogen atmosphere to obtain a mixture After completion of the dropwise addition to react at the same temperature for 12 hours

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 2-Chlorobenzonitrile (27.5 g, 0.2 mol), monochlorobenzene (30.0 g), and a 50% by weight aqueous solution (1.0 g) of tetra-n-butyl ammonium bromide were placed in a 500-ml four-necked flask equipped with a stirrer, a thermometer, a dropping funnel, and a condenser under a nitrogen atmosphere to obtain a mixture. A 30% by weight aqueous solution (51.4 g) of sodium salt of methanethiol (0.22 mol) was added dropwise to the mixture at 60 to 65° C. over a period of 5 hours under stirring. After completion of the dropwise addition, the mixture was further allowed to react at the same temperature for 12 hours. By this operation, 2-(methylthio)benzonitrile was obtained. equipped with a stirrer a thermometer, a dropping funnel, and a condenser under a nitrogen atmosphere to obtain a mixture After completion of the dropwise addition to react at the same temperature for 12 hours

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A solution of 2-(methylthio)benzonitrile (29.8 g) in dry ether (150 ml) was added dropwise to a stirred suspension of lithium aluminium hydride (1.16 g) in dry ether (360ml) under nitrogen. A thick gum formed which was dissolved by the addition of dry THF (100 ml). The mixture was stirred at room temperature for 2 hours. Water (12 ml) was then carefully added followed by a 15% aqueous solution of sodium hydroxide (36 ml) and more water (12 ml). The mixture was filtered, the filtrate washed with water, dried and evaporated in vacuo. The residue was distilled in vacuo to give a colourless oil. Yield=20.9 g. A thick gum formed which The mixture was filtered the filtrate washed with water dried evaporated in vacuo The residue was distilled in vacuo to give a colourless oil

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a 500 ml four-necked flask equipped with a stirrer, a thermometer, and a condenser, 29.8 g (0.2 mol) of 2-(methylthio)benzonitrile, 100 g of monochlorobenzene, and 4.32 g (0.24 mol) of water were added. To the flask, 29.7 g (0.22 mol) of sulfuryl chloride was added with stirring at a temperature of from 5° to 15° C., heated to a temperature of from 70° to 80° C., and allowed to react for 1 hour. After the completion of the reaction, the reaction mixture was cooled to room temperature to precipitate white crystals. The white crystals were washed with monochlorobenzene, and dried to give 29.0 g of 1,2-benzisothiazol-3-one (melting point: 157° to 158° C.). The yield of the product was 96% against the starting 2-(methylthio)benzonitrile. To a 500 ml four-necked flask equipped with a stirrer heated to a temperature of from 70° to 80° C. to react for 1 hour After the completion of the reaction to precipitate white crystals The white crystals were washed with monochlorobenzene dried

反応条件: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 74.5 g (0.500 mol) of 2-cyanophenyl methyl sulfide and 250 g of chlorobenzene were placed in a 500 ml four-neck flask equipped with a stirrer, a thermometer, a dropping funnel and a condenser and 96.0 g (0.600 mol) of bromine was added dropwise thereto at about 100° C. over five hours while stirring, followed by stirring for two hours to complete the reaction. The excess bromine was removed with an aqueous sodium carbonate solution and the solvent was distilled off to obtain 92.0 g of crude 2-cyanobenzenesulfenyl bromide. Separately, 172.4 g (2.00 mol) of piperazine and 15 g of chlorobenzene were placed in a 1000 ml four-neck flask equipped with a stirrer, a thermometer, a dropping funnel and a condenser and the molten crude 2-cyanobenzenesulfenyl bromide obtained above was added dropwise thereto at about 130° C. over one hour while stirring, followed by stirring for five hours to complete the reaction. The excess piperazine was removed with water and reaction mixture was acidified with hydrochloric acid, followed by extraction into an aqueous layer. The aqueous layer was basified with an aqueous sodium hydroxide solution to obtain 65.9 g of 3-(1-piperazinyl)-1,2-benzisothiazole as crystals. The yield starting from 2-cyanophenyl methyl sulfide was 60.2%. equipped with a stirrer by stirring for two hours the reaction The excess bromine was removed with an aqueous sodium carbonate solution the solvent was distilled off

反応条件: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 74.5 g (0.500 mol) of 2-cyanophenyl methyl sulfide and 250 g of chlorobenzene were placed in a 500 ml four-neck flask equipped with a stirrer, a thermometer, a dropping funnel and a condenser and 96.0 g (0.600 mol) of bromine was added dropwise thereto at about 100° C. over five hours while stirring. The excess bromine was removed with an aqueous sodium carbonate solution, followed by distillation under reduced pressure to obtain 90.4 g of 2-cyanobenzenesulfenyl bromide. The yield starting from 2-cyanophenyl methyl sulfide was 84.5%. equipped with a stirrer The excess bromine was removed with an aqueous sodium carbonate solution followed by distillation under reduced pressure

反応条件: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 74.5 g (0.500 mol) of 2-cyanophenyl methyl sulfide and 250 g of chlorobenzene were placed in a 500 ml four-neck flask equipped with a stirrer, a thermometer, a dropping funnel and a condenser and 96.0 g (0.600 mol) of bromine was added dropwise thereto at about 100° C. over five hours while stirring, followed by stirring for two hours to complete the reaction. The excess bromine was removed with an aqueous sodium carbonate solution and the solvent was distilled off to obtain 92.0 g of crude 2-cyanobenzenesulfenyl bromide. Separately, 172.4 g (2.00 mol) of piperazine and 15 g of chlorobenzene were placed in a 1000 ml four-neck flask equipped with a stirrer, a thermometer, a dropping funnel and a condenser and the molten crude 2-cyanobenzenesulfenyl bromide obtained above was added dropwise thereto at about 130° C. over one hour while stirring, followed by stirring for five hours to complete the reaction. The excess piperazine was removed with water and reaction mixture was acidified with hydrochloric acid, followed by extraction into an aqueous layer. The aqueous layer was basified with an aqueous sodium hydroxide solution to obtain 65.9 g of 3-(1-piperazinyl)-1,2-benzisothiazole as crystals. The yield starting from 2-cyanophenyl methyl sulfide was 60.2%. equipped with a stirrer by stirring for two hours the reaction The excess bromine was removed with an aqueous sodium carbonate solution the solvent was distilled off