N-(2-methylphenyl)benzenesulfonamide

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The so far single industrially feasible synthesis is described by BIOS Final Report 986/2, No. 167, pages 297-306, and involves acylating 2-aminotoluene with benzenesulfonyl chloride to give N-(2-methylphenyl)-benzenesulfonamide, nitrating the latter in chlorobenzene, and, finally, splitting off the protective group by hydrolysis and isolating 2-amino-5-nitrotoluene. This synthesis gives a yield of about 75% of theory. In addition to this unsatisfactory yield, the numerous process stages and the associated consumption of chemicals, this process harbors further grave disadvantages which render its industrial application problematical from a processing and an ecological point of veiw The so far single industrially feasible synthesis

Conditions: temp:-72.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To tetrahydrofuran (200 mL) was added N-o-tolyl-benzenesulfonamide (4.95 g, 20 mmol). After cooling to −72° C., a solution of n-butyllithium (1.6 M, 25 mL in hexane) was added, and the mixture was stirred for 3 hours at −72° C. A solution of 3-methoxy-4,5-methylenedioxybenzaldehyde (3.60 g, 20 mmol) in tetrahydrofuran (70 mL) was added, and the mixture was stirred and warmed to 0° C. over 1.5 hours. The mixture was poured into 200-mL saturated ammonium chloride solution, and the organic phase was decanted. The solvent was evaporated in vacuo and the residue was suspended in ethyl ether, washed with saturated sodium bicarbonate and brine solutions. The solution was dried over anhydrous magnesium sulfate, filtered, and evaporated to give a syrup which was chromatographed on 500 g silica gel eluted with a mixture of ethyl acetate and hexane (35:65). The appropriate fractions were concentrated in vacuo and crystallized giving a solid, 4.15 g, 48.6% yield, mp 155-158° C. NMR spectra and elemental analysis were consistent with the structure. the mixture was stirred warmed to 0° C. over 1.5 hours the organic phase was decanted The solvent was evaporated in vacuo washed with saturated sodium bicarbonate and brine solutions The solution was dried over anhydrous magnesium sulfate filtered evaporated to give a syrup which was chromatographed on 500 g silica gel eluted with a mixture of ethyl acetate and hexane (35:65) The appropriate fractions were concentrated in vacuo crystallized giving a solid, 4.15 g, 48.6% yield, mp 155-158° C

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The so far single industrially feasible synthesis is described by BIOS Final Report 986/2, No. 167, pages 297-306, and involves acylating 2-aminotoluene with benzenesulfonyl chloride to give N-(2-methylphenyl)-benzenesulfonamide, nitrating the latter in chlorobenzene, and, finally, splitting off the protective group by hydrolysis and isolating 2-amino-5-nitrotoluene. This synthesis gives a yield of about 75% of theory. In addition to this unsatisfactory yield, the numerous process stages and the associated consumption of chemicals, this process harbors further grave disadvantages which render its industrial application problematical from a processing and an ecological point of veiw The so far single industrially feasible synthesis

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The so far single industrially feasible synthesis is described by BIOS Final Report 986/2, No. 167, pages 297-306, and involves acylating 2-aminotoluene with benzenesulfonyl chloride to give N-(2-methylphenyl)-benzenesulfonamide, nitrating the latter in chlorobenzene, and, finally, splitting off the protective group by hydrolysis and isolating 2-amino-5-nitrotoluene. This synthesis gives a yield of about 75% of theory. In addition to this unsatisfactory yield, the numerous process stages and the associated consumption of chemicals, this process harbors further grave disadvantages which render its industrial application problematical from a processing and an ecological point of veiw The so far single industrially feasible synthesis

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:-72.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To tetrahydrofuran (200 mL) was added N-o-tolyl-benzenesulfonamide (4.95 g, 20 mmol). After cooling to −72° C., a solution of n-butyllithium (1.6 M, 25 mL in hexane) was added, and the mixture was stirred for 3 hours at −72° C. A solution of 3-methoxy-4,5-methylenedioxybenzaldehyde (3.60 g, 20 mmol) in tetrahydrofuran (70 mL) was added, and the mixture was stirred and warmed to 0° C. over 1.5 hours. The mixture was poured into 200-mL saturated ammonium chloride solution, and the organic phase was decanted. The solvent was evaporated in vacuo and the residue was suspended in ethyl ether, washed with saturated sodium bicarbonate and brine solutions. The solution was dried over anhydrous magnesium sulfate, filtered, and evaporated to give a syrup which was chromatographed on 500 g silica gel eluted with a mixture of ethyl acetate and hexane (35:65). The appropriate fractions were concentrated in vacuo and crystallized giving a solid, 4.15 g, 48.6%o yield, mp 155-158° C. NMR spectra and elemental analysis were consistent with the structure. the mixture was stirred warmed to 0° C. over 1.5 hours the organic phase was decanted The solvent was evaporated in vacuo washed with saturated sodium bicarbonate and brine solutions The solution was dried over anhydrous magnesium sulfate filtered evaporated to give a syrup which was chromatographed on 500 g silica gel eluted with a mixture of ethyl acetate and hexane (35:65) The appropriate fractions were concentrated in vacuo crystallized giving a solid, 4.15 g, 48.6%o yield

Conditions: temp:-72.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To tetrahydrofuran (200 mL) was added N-o-tolyl-benzenesulfonamide (4.95 g, 20 mmol). After cooling to −72° C., a solution of n-butyllithium (1.6 M, 25 mL in hexane) was added, and the mixture was stirred for 3 hours at −72° C. A solution of 3-methoxy-4,5-methylenedioxybenzaldehyde (3.60 g, 20 mmol) in tetrahydrofuran (70 mL) was added, and the mixture was stirred and warmed to 0° C. over 1.5 hours. The mixture was poured into 200-mL saturated ammonium chloride solution, and the organic phase was decanted. The solvent was evaporated in vacuo and the residue was suspended in ethyl ether, washed with saturated sodium bicarbonate and brine solutions. The solution was dried over anhydrous magnesium sulfate, filtered, and evaporated to give a syrup which was chromatographed on 500 g silica gel eluted with a mixture of ethyl acetate and hexane (35:65). The appropriate fractions were concentrated in vacuo and crystallized giving a solid, 4.15 g, 48.6%o yield, mp 155-158° C. NMR spectra and elemental analysis were consistent with the structure. the mixture was stirred warmed to 0° C. over 1.5 hours the organic phase was decanted The solvent was evaporated in vacuo washed with saturated sodium bicarbonate and brine solutions The solution was dried over anhydrous magnesium sulfate filtered evaporated to give a syrup which was chromatographed on 500 g silica gel eluted with a mixture of ethyl acetate and hexane (35:65) The appropriate fractions were concentrated in vacuo crystallized giving a solid, 4.15 g, 48.6%o yield

Conditions: temp:-72.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To tetrahydrofuran (200 mL) was added N-o-tolyl-benzenesulfonamide (4.95 g, 20 mmol). After cooling to −72° C. a solution of n-butyllithium (1.6 M, 25 mL in hexane) was added, and the mixture was stirred for 3 hours at −72° C. A solution of 3-methoxy-4,5-methylenedioxybenzaldehyde (3.60 g, 20 mmol) in tetrahydrofuran (70 mL) was added, and the mixture was stirred and warmed to 0° C. over 1.5 hours. The mixture was poured into 200-mL saturated ammonium chloride solution, and the organic phase was decanted. The solvent was evaporated in vacuo and the residue was suspended in ethyl ether, washed with saturated sodium bicarbonate and brine solutions. The solution was dried over anhydrous magnesium sulfate, filtered, and evaporated to give a syrup which was chromatographed on 500 g silica gel eluted with a mixture of ethyl acetate and hexane (35:65). The appropriate fractions were concentrated in vacuo and crystallized giving a solid, 4.15 g, 48.6% yield, mp 155-158° C. NMR spectra and elemental analysis were consistent with the structure. was added the mixture was stirred warmed to 0° C. over 1.5 hours the organic phase was decanted The solvent was evaporated in vacuo washed with saturated sodium bicarbonate and brine solutions The solution was dried over anhydrous magnesium sulfate filtered evaporated to give a syrup which was chromatographed on 500 g silica gel eluted with a mixture of ethyl acetate and hexane (35:65) The appropriate fractions were concentrated in vacuo crystallized giving a solid, 4.15 g, 48.6% yield, mp 155-158° C

Conditions: temp:-72.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To tetrahydrofuran (200 mL) was added N-o-tolyl-benzenesulfonamide (4.95 g, 20 mmol). After cooling to −72° C., a solution of n-butyllithium (1.6 M, 25 mL in hexane) was added, and the mixture was stirred for 3 hours at −72° C. A solution of 3-methoxy-4,5-methylenedioxybenzaldehyde (3.60 g, 20 mmol) in tetrahydrofuran (70 mL) was added, and the mixture was stirred and warmed to 0° C. over 1.5 hours. The mixture was poured into 200-mL saturated ammonium chloride solution, and the organic phase was decanted. The solvent was evaporated in vacuo and the residue was suspended in ethyl ether, washed with saturated sodium bicarbonate and brine solutions. The solution was dried over anhydrous magnesium sulfate, filtered, and evaporated to give a syrup which was chromatographed on 500 g silica gel eluted with a mixture of ethyl acetate and hexane (35:65). The appropriate fractions were concentrated in vacuo and crystallized giving a solid, 4.15 g, 48.6% yield, mp 155-158° C. NMR spectra and elemental analysis were consistent with the structure. the mixture was stirred warmed to 0° C. over 1.5 hours the organic phase was decanted The solvent was evaporated in vacuo washed with saturated sodium bicarbonate and brine solutions The solution was dried over anhydrous magnesium sulfate filtered evaporated to give a syrup which was chromatographed on 500 g silica gel eluted with a mixture of ethyl acetate and hexane (35:65) The appropriate fractions were concentrated in vacuo crystallized giving a solid, 4.15 g, 48.6% yield, mp 155-158° C

Conditions: temp:-72.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To tetrahydrofuran (200 mL) was added N-o-tolyl-benzenesulfonamide (4.95 g, 20 mmol). After cooling to −72° C., a solution of n-butyllithium (1.6 M, 25 mL in hexane) was added, and the mixture was stirred for 3 hours at −72° C. A solution of 3-methoxy-4,5-methylenedioxybenzaldehyde (3.60 g, 20 mmol) in tetrahydrofuran (70 mL) was added, and the mixture was stirred and warmed to 0° C. over 1.5 hours. The mixture was poured into 200-mL saturated ammonium chloride solution, and the organic phase was decanted. The solvent was evaporated in vacuo and the residue was suspended in ethyl ether, washed with saturated sodium bicarbonate and brine solutions. The solution was dried over anhydrous magnesium sulfate, filtered, and evaporated to give a syrup which was chromatographed on 500 g silica gel eluted with a mixture of ethyl acetate and hexane (35:65). The appropriate fractions were concentrated in vacuo and crystallized giving a solid, 4.15 g, 48.6% yield, mp 155-158° C. NMR spectra and elemental analysis were consistent with the structure. the mixture was stirred warmed to 0° C. over 1.5 hours the organic phase was decanted The solvent was evaporated in vacuo washed with saturated sodium bicarbonate and brine solutions The solution was dried over anhydrous magnesium sulfate filtered evaporated to give a syrup which was chromatographed on 500 g silica gel eluted with a mixture of ethyl acetate and hexane (35:65) The appropriate fractions were concentrated in vacuo crystallized giving a solid, 4.15 g, 48.6% yield, mp 155-158° C

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The so far single industrially feasible synthesis is described by BIOS Final Report 986/2, No. 167, pages 297-306, and involves acylating 2-aminotoluene with benzenesulfonyl chloride to give N-(2-methylphenyl)-benzenesulfonamide, nitrating the latter in chlorobenzene, and, finally, splitting off the protective group by hydrolysis and isolating 2-amino-5-nitrotoluene. This synthesis gives a yield of about 75% of theory. In addition to this unsatisfactory yield, the numerous process stages and the associated consumption of chemicals, this process harbors further grave disadvantages which render its industrial application problematical from a processing and an ecological point of veiw The so far single industrially feasible synthesis