3-methyl-2-methylsulfonylaniline

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: 400 g (2.9 mol) of potassium carbonate were added to a solution of 134 g (0.73 mol) of 3-methyl-2-methylsulfonylaniline in 1200 ml of acetonitrile. At room temperature, 320 g (0.65 mol) of tetrabutylammonium tribromide were then added a little at a time, with vigorous stirring. The resulting precipitate was separated off, methyl tert-butyl ether was added to the filtrate and the filtrate was extracted with dilute hydrochloric acid and then with water. The organic phase was concentrated to dryness under reduced pressure. The resulting residue was once more taken up in methyl tert-butyl ether and washed two more times with hydrochloric acid and water. The organic phase was dried and concentrated under reduced pressure, giving 142 g (74%) of 4-bromo-3-methyl-2-methylsulfonylaniline as a brown solid of melting point 103–106° C. The resulting precipitate was separated off methyl tert-butyl ether was added to the filtrate the filtrate was extracted with dilute hydrochloric acid The organic phase was concentrated to dryness under reduced pressure washed two more times with hydrochloric acid and water The organic phase was dried concentrated under reduced pressure

反応条件: temp:45.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A solution of 158 g (0.74 mol) of 3-methyl-2-methylsulfonylnitrobenzene in 1.5 l of ethyl acetate and 5 g of a catalyst comprising 10% by weight of palladium on carbon were introduced into a hydrogenation apparatus fitted with gas inlet tube. The hydrogenation apparatus was flushed twice with nitrogen. Hydrogen was then introduced, and the mixture was stirred at 45° C. for 48 hours. The reaction mixture was filtered off with suction through kieselguhr and the filtrate was concentrated under reduced pressure, giving 134 g (98% of theory) of 3-methyl-2-methylsulfonylaniline as an orange-yellow solid. were introduced into a hydrogenation apparatus fitted with gas inlet tube The hydrogenation apparatus was flushed twice with nitrogen Hydrogen was then introduced The reaction mixture was filtered off with suction through kieselguhr the filtrate was concentrated under reduced pressure

反応条件: temp:45.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A solution of 158 g (0.74 mol) of 3-methyl-2-methylsulfonylnitrobenzene in 1.5 l of ethyl acetate and 5 g of a catalyst comprising 10% by weight of palladium on carbon were introduced into a hydrogenation apparatus fitted with gas inlet tube. The hydrogenation apparatus was flushed twice with nitrogen. Hydrogen was then introduced, and the mixture was stirred at 45° C. for 48 hours. The reaction mixture was filtered off with suction through kieselguhr and the filtrate was concentrated under reduced pressure, giving 134 g (98% of theory) of 3-methyl-2-methylsulfonylaniline as an orange-yellow solid. were introduced into a hydrogenation apparatus fitted with gas inlet tube The hydrogenation apparatus was flushed twice with nitrogen Hydrogen was then introduced The reaction mixture was filtered off with suction through kieselguhr the filtrate was concentrated under reduced pressure

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

実験手順: 400 g (2.9 mol) of potassium carbonate were added to a solution of 134 g (0.73 mol) of 3-methyl-2-methylsulfonylaniline in 1200 ml of acetonitrile. At room temperature, 320 g (0.65 mol) of tetrabutylammonium tribromide were then added a little at a time, with vigorous stirring. The resulting precipitate was separated off, methyl tert-butyl ether was added to the filtrate and the filtrate was extracted with dilute hydrochloric acid and then with water. The organic phase was concentrated to dryness under reduced pressure. The resulting residue was once more taken up in methyl tert-butyl ether and washed two more times with hydrochloric acid and water. The organic phase was dried and concentrated under reduced pressure, giving 142 g (74%) of 4-bromo-3-methyl-2-methylsulfonylaniline as a brown solid of melting point 103–106° C. The resulting precipitate was separated off methyl tert-butyl ether was added to the filtrate the filtrate was extracted with dilute hydrochloric acid The organic phase was concentrated to dryness under reduced pressure washed two more times with hydrochloric acid and water The organic phase was dried concentrated under reduced pressure

反応条件: temp:45.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A solution of 158 g (0.74 mol) of 3-methyl-2-methylsulfonylnitrobenzene in 1.5 l of ethyl acetate and 5 g of a catalyst comprising 10% by weight of palladium on carbon were introduced into a hydrogenation apparatus fitted with gas inlet tube. The hydrogenation apparatus was flushed twice with nitrogen. Hydrogen was then introduced, and the mixture was stirred at 45° C. for 48 hours. The reaction mixture was filtered off with suction through kieselguhr and the filtrate was concentrated under reduced pressure, giving 134 g (98% of theory) of 3-methyl-2-methylsulfonylaniline as an orange-yellow solid. were introduced into a hydrogenation apparatus fitted with gas inlet tube The hydrogenation apparatus was flushed twice with nitrogen Hydrogen was then introduced The reaction mixture was filtered off with suction through kieselguhr the filtrate was concentrated under reduced pressure