N-(3-bromophenyl)-3-oxobutanamide

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

実験手順: 6.65 g (26.00 mM) of N-(3-bromophenyl)-3-oxobutyramide was heated in 30 mL of conc. sulfuric acid to 120° C. (oil bath temperature) for 1.5 h. The reaction mixture was then poured into ice, whereby precipitate was formed. This was filtered and washed repeatedly with water. After drying, it was recrystallised in 95% ethanol, providing 5.21 g (84%) of the product as a white solid: mp 275°-276° C.; The reaction mixture was then poured into ice whereby precipitate was formed This was filtered washed repeatedly with water After drying it was recrystallised in 95% ethanol

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

実験手順: 6.65 g (26.00 mM) of N-(3-bromophenyl)-3-oxobutyramide was heated in 30 mL of conc. sulfuric acid to 120° C. (oil bath temperature) for 1.5 h. The reaction mixture was then poured into ice, whereby precipitate was formed. This was filtered and washed repeatedly with water. After drying, it was recrystallised in 95% ethanol, providing 5.21 g (84%) of the product as a white solid: mp 275°-276° C.; The reaction mixture was then poured into ice whereby precipitate was formed This was filtered washed repeatedly with water After drying it was recrystallised in 95% ethanol

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

実験手順: To a heated (80° C., oil bath temperature) solution of 20.00 g (0.12M) of m-bromoaniline in 200 mL of dry toluene was added dropwise over a period of 30 min. 12 g (0.14M) of diketene in 100 mL of dry toluene. When the addition was completed, the reaction mixture was brought to reflux for 5 h. The toluene was then removed in vacuo, resulting in a yellow solid. Recrystallisation from toluene afforded 14.70 g (48%) of product as light pink crystals: mp 94°-95° C. was added dropwise over a period of 30 min When the addition to reflux for 5 h The toluene was then removed in vacuo resulting in a yellow solid Recrystallisation from toluene

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

実験手順: To a heated (80° C., oil bath temperature) solution of 20.00 g (0.12M) of m-bromoaniline in 200 mL of dry toluene was added dropwise over a period of 30 min. 12 g (0.14M) of diketene in 100 mL of dry toluene. When the addition was completed, the reaction mixture was brought to reflux for 5 h. The toluene was then removed in vacuo, resulting in a yellow solid. Recrystallisation from toluene afforded 14.70 g (48%) of product as light pink crystals: mp 94°-95° C. was added dropwise over a period of 30 min When the addition to reflux for 5 h The toluene was then removed in vacuo resulting in a yellow solid Recrystallisation from toluene

反応条件: temp:20.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A mixture of 68.5 g of m-bromo-acetylacetanilide, 39.6 g of methyl orthoformate, 160 ml of methanol and 0.5 g of p-toluene sulfonic acid was stirred for 2 hours at 20° C and after the addition of 1 ml of quinoline, the mixture was evaporated to dryness under reduced pressure. The 83 g of colorless oil residue was taken up in 400 ml of toluene and the mixture was heated at 140° C for 4 hours while distilling the toluene-methanol azeotrope formed. After cooling, the toluene was evaporated under reduced pressure and the residue was chromatographed over silica gel. The product was eluted with a 9-1 mixture of methylene chloride and ethyl acetate and the fraction with an Rf = 0.65 was taken up in isopropyl ether to obtain 44 g of m-bromo-3-methoxy-crotonanilide melting at 110° C. the mixture was evaporated to dryness under reduced pressure the mixture was heated at 140° C for 4 hours while distilling the toluene-methanol azeotrope formed After cooling the toluene was evaporated under reduced pressure the residue was chromatographed over silica gel The product was eluted with a 9-1 mixture of methylene chloride and ethyl acetate

反応条件: temp:20.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 84 g of diketene were added over 20 minutes to a mixture of 172 g of m-bromo-aniline and 600 ml of benzene and the mixture was stirred for 5 hours at 20° C. The mixture was filtered and the precipitate was washed with benzene and isopropyl ether. The filtrate was vacuum filtered and evaporated to dryness to obtain 189 g of m-bromo-acetylacetanilide melting at 110° C. The mixture was filtered the precipitate was washed with benzene and isopropyl ether filtered evaporated to dryness

反応条件: temp:20.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 84 g of diketene were added over 20 minutes to a mixture of 172 g of m-bromo-aniline and 600 ml of benzene and the mixture was stirred for 5 hours at 20° C. The mixture was filtered and the precipitate was washed with benzene and isopropyl ether. The filtrate was vacuum filtered and evaporated to dryness to obtain 189 g of m-bromo-acetylacetanilide melting at 110° C. The mixture was filtered the precipitate was washed with benzene and isopropyl ether filtered evaporated to dryness

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

実験手順: 6.65 g (26.00 mM) of N-(3-bromophenyl)-3-oxobutyramide was heated in 30 mL of conc. sulfuric acid to 120° C. (oil bath temperature) for 1.5 h. The reaction mixture was then poured into ice, whereby precipitate was formed. This was filtered and washed repeatedly with water. After drying, it was recrystallised in 95% ethanol, providing 5.21 g (84%) of the product as a white solid: mp 275°-276° C.; The reaction mixture was then poured into ice whereby precipitate was formed This was filtered washed repeatedly with water After drying it was recrystallised in 95% ethanol

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

実験手順: To a heated (80° C., oil bath temperature) solution of 20.00 g (0.12M) of m-bromoaniline in 200 mL of dry toluene was added dropwise over a period of 30 min. 12 g (0.14M) of diketene in 100 mL of dry toluene. When the addition was completed, the reaction mixture was brought to reflux for 5 h. The toluene was then removed in vacuo, resulting in a yellow solid. Recrystallisation from toluene afforded 14.70 g (48%) of product as light pink crystals: mp 94°-95° C. was added dropwise over a period of 30 min When the addition to reflux for 5 h The toluene was then removed in vacuo resulting in a yellow solid Recrystallisation from toluene

反応条件: temp:20.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A mixture of 68.5 g of m-bromo-acetylacetanilide, 39.6 g of methyl orthoformate, 160 ml of methanol and 0.5 g of p-toluene sulfonic acid was stirred for 2 hours at 20° C and after the addition of 1 ml of quinoline, the mixture was evaporated to dryness under reduced pressure. The 83 g of colorless oil residue was taken up in 400 ml of toluene and the mixture was heated at 140° C for 4 hours while distilling the toluene-methanol azeotrope formed. After cooling, the toluene was evaporated under reduced pressure and the residue was chromatographed over silica gel. The product was eluted with a 9-1 mixture of methylene chloride and ethyl acetate and the fraction with an Rf = 0.65 was taken up in isopropyl ether to obtain 44 g of m-bromo-3-methoxy-crotonanilide melting at 110° C. the mixture was evaporated to dryness under reduced pressure the mixture was heated at 140° C for 4 hours while distilling the toluene-methanol azeotrope formed After cooling the toluene was evaporated under reduced pressure the residue was chromatographed over silica gel The product was eluted with a 9-1 mixture of methylene chloride and ethyl acetate

反応条件: temp:20.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 84 g of diketene were added over 20 minutes to a mixture of 172 g of m-bromo-aniline and 600 ml of benzene and the mixture was stirred for 5 hours at 20° C. The mixture was filtered and the precipitate was washed with benzene and isopropyl ether. The filtrate was vacuum filtered and evaporated to dryness to obtain 189 g of m-bromo-acetylacetanilide melting at 110° C. The mixture was filtered the precipitate was washed with benzene and isopropyl ether filtered evaporated to dryness

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

実験手順: 6.65 g (26.00 mM) of N-(3-bromophenyl)-3-oxobutyramide was heated in 30 mL of conc. sulfuric acid to 120° C. (oil bath temperature) for 1.5 h. The reaction mixture was then poured into ice, whereby precipitate was formed. This was filtered and washed repeatedly with water. After drying, it was recrystallised in 95% ethanol, providing 5.21 g (84%) of the product as a white solid: mp 275°-276° C.; The reaction mixture was then poured into ice whereby precipitate was formed This was filtered washed repeatedly with water After drying it was recrystallised in 95% ethanol