methyl 2-chlorosulfonyl-6-fluorobenzoate

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:24.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: AT 20 to 28° C. and while stirring, 42.5 g of ammonia was gassed into mixture of 252.6 g (1 mol) of methyl 2-chlorosulfonyl-6-fluorobenzoate in 700 ml of anhydrous tetrahydrofuran. After the mixture had been stirred for an hour at 25° C., the precipitate was filtered off, dissolved in water, and extracted once with ethyl acetate. Acidification of the aqueous phase with concentrated hydrochloric acid gave 4% of theory of 4-fluoro-1,2-benzisothiazol-3-one-1,1-dioxide of m.p. 210 to 212° C. After the mixture had been stirred for an hour at 25° C. the precipitate was filtered off dissolved in water extracted once with ethyl acetate

反応条件: temp:24.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: AT 20 to 28° C. and while stirring, 42.5 g of ammonia was gassed into mixture of 252.6 g (1 mol) of methyl 2-chlorosulfonyl-6-fluorobenzoate in 700 ml of anhydrous tetrahydrofuran. After the mixture had been stirred for an hour at 25° C., the precipitate was filtered off, dissolved in water, and extracted once with ethyl acetate. Acidification of the aqueous phase with concentrated hydrochloric acid gave 4% of theory of 4-fluoro-1,2-benzisothiazol-3-one-1,1-dioxide of m.p. 210 to 212° C. After the mixture had been stirred for an hour at 25° C. the precipitate was filtered off dissolved in water extracted once with ethyl acetate

反応条件: temp:5.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: At 5° C. and while stirring, 108 g (0.64 mol) of methyl 6-fluoroanthranilate and 45 g (0.65 mol) of sodium nitrite in 106 ml of water were added separately but simultaneously over a period of 1 hour in such a manner to 250 ml of concentrated hydrochloric acid that the ester component was in an excess. After the reaction mixture had been stirred for 20 minutes at 5 to 8° C., it was poured all at once into a prepared solution of 53 g of sulfur dioxide, 1.7 g of copper (II) chloride in a small amount of water and 200 ml of 1,2-dichloroethane, and stirred for a further 10 minutes. The mixture was heated slowly to 50° C. and stirred for ninety minutes while passing in 46 g of sulfur dioxide. The mixture was then cooled to 20° C. and 5.5 g of chlorine was passed in over a 20-minute period while stirring. The organic phase was then separated, washed with water and dried. There was obtained 65% of theory of the title compound as a brownish oil. After the reaction mixture had been stirred for 20 minutes at 5 to 8° C. stirred for a further 10 minutes The mixture was heated slowly to 50° C. stirred for ninety minutes The mixture was then cooled to 20° C. was passed in over a 20-minute period while stirring The organic phase was then separated washed with water dried

反応条件: temp:50.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 108 g of methyl 6-fluoroanthranilate and 45 g of sodium nitrite in 106 ml of water were added, via 2 feed devices, to 250 ml of stirred concentrated hydrochloric acid at 5° C. over the course of 1 hour in such a way that the ester component was present in excess. After the reaction mixture had been stirred for 20 minutes at 55° C.-8° C. it was poured, in one shot, into a previously prepared solution of 53 g of sulfur dioxide, 1.7 g of copper(II) chloride and a small amount of water in 200 ml of 1,2-dichloroethane, and the resulting mixture was stirred for 10 minutes thereafter. It was then slowly heated to 50° C. and stirred for 11/2 hours while introducing 46 g of sulfur dioxide. It was then cooled to 20° C. and 5.5 g of chlorine were introduced over 20 minutes, with stirring. Stirring was then continued for 20 minutes, after which the organic phase was separated off. It was washed with water, dried over magnesium sulfate and evaporated, giving 105 g of the compound shown in the title, in the form of a brownish oil. stirred for 11/2 hours It was then cooled to 20° C. with stirring Stirring was then continued for 20 minutes after which the organic phase was separated off It was washed with water dried over magnesium sulfate evaporated

反応条件: temp:50.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 108 g of methyl 6-fluoroanthranilate and 45 g of sodium nitrite in 106 ml of water were added, via 2 feed devices, to 250 ml of stirred concentrated hydrochloric acid at 5° C. over the course of 1 hour in such a way that the ester component was present in excess. After the reaction mixture had been stirred for 20 minutes at 55° C.-8° C. it was poured, in one shot, into a previously prepared solution of 53 g of sulfur dioxide, 1.7 g of copper(II) chloride and a small amount of water in 200 ml of 1,2-dichloroethane, and the resulting mixture was stirred for 10 minutes thereafter. It was then slowly heated to 50° C. and stirred for 11/2 hours while introducing 46 g of sulfur dioxide. It was then cooled to 20° C. and 5.5 g of chlorine were introduced over 20 minutes, with stirring. Stirring was then continued for 20 minutes, after which the organic phase was separated off. It was washed with water, dried over magnesium sulfate and evaporated, giving 105 g of the compound shown in the title, in the form of a brownish oil. stirred for 11/2 hours It was then cooled to 20° C. with stirring Stirring was then continued for 20 minutes after which the organic phase was separated off It was washed with water dried over magnesium sulfate evaporated

反応条件: temp:0.00; pressure:0.00; stir:

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: At 20° to 28° C. and while stirring, 42.5 g of ammonia was gassed into a mixture of 252.6 g (1 mol) of methyl 2-chlorosulfonyl-6-fluorobenzoate in 700 ml of anhydrous tetrahydrofuran. After the mixture had been stirred for an hour at 25° C., the precipitate was filtered off, dissolved in water, and extracted once with ethyl acetate. Acidification of the aqueous phase with concentrated hydrochloric acid gave 4% of theory of 4-fluoro-1,2-benzisothiazol-3-one-1,1-dioxide of m.p. 210° to 212° C. After the mixture had been stirred for an hour at 25° C. the precipitate was filtered off dissolved in water extracted once with ethyl acetate

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

実験手順: At 20° to 28° C. and while stirring, 42.5 g of ammonia was gassed into a mixture of 252.6 g (1 mol) of methyl 2-chlorosulfonyl-6-fluorobenzoate in 700 ml of anhydrous tetrahydrofuran. After the mixture had been stirred for an hour at 25° C., the precipitate was filtered off, dissolved in water, and extracted once with ethyl acetate. Acidification of the aqueous phase with concentrated hydrochloric acid gave 4% of theory of 4-fluoro-1,2-benzisothiazol-3-one-1,1-dioxide of m.p. 210° to 212° C. After the mixture had been stirred for an hour at 25° C. the precipitate was filtered off dissolved in water extracted once with ethyl acetate

反応条件: temp:5.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: At 5° C. and while stirring, 108 g (0.64 mol) of methyl 6-fluoroanthranilate and 45 g (0.65 mol) of sodium nitrite in 106 ml of water were added separately but simultaneously over a period of 1 hour in such a manner to 250 ml of concentrated hydrochloric acid that the ester component was in an excess. After the reaction mixture had been stirred for 20 minutes at 5° to 8° C., it was poured all at once into a prepared solution of 53 g of sulfur dioxide, 1.7 g of copper(II) chloride in a small amount of water and 200 ml of 1,2-dichloroethane, and stirred for a further 10 minutes. The mixture was heated slowly to 50° C. and stirred for ninety minutes while passing in 46 g of sulfur dioxide. The mixture was then cooled to 20° C. and 5.5 g of chlorine was passed in over a 20-minute period while stirring. The organic phase was then separated, washed with water and dried. There was obtained 65% of theory of the title compound as a brownish oil. After the reaction mixture had been stirred for 20 minutes at 5° to 8° C. stirred for a further 10 minutes The mixture was heated slowly to 50° C. stirred for ninety minutes The mixture was then cooled to 20° C. was passed in over a 20-minute period while stirring The organic phase was then separated washed with water dried