N-苄基氨基乙腈盐酸盐

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: The starting material for the abovementioned synthetic route a), viz. N-benzyl-aminoacetonitrile, is prepared by reaction of benzylamine and formaldehyde with the extremely toxic hydrocyanic acid (see also Tetrahedron Letters [23], 27 (1982), 2741-4). The starting material for the synthetic route b), viz. N-benzylglycine, also firstly has to be prepared by reaction of glycine with benzyl chloride or of chloroacetic acid with benzylamine. The reaction of N-benzylaminoacetonitrile or N-benzylglycine as per a) or b) is carried out either by fusion with urea for a long time or by reaction with the toxic cyanic acid. Both methods give 1-benzyl-hydantoin in only low yields: thus, according to Huaxue Shiji 1993, 15(1) 15-16, the reaction of N-benzylglycine (obtained by reaction of benzylarnine with chloroacetic acid) with cyanic acid gives 1-benzylhydantoin in a yield of only 39.5% and the reaction of N-benzylglycine with urea gives 1-benzylhydantoin in a yield of only 45.6%. The subsequent bromination of the 1-benzylhydantoin and treatment with ethanol again proceeds in only a low yield of 42.7%.

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: The starting material for the abovementioned synthetic route a), viz. N-benzyl-aminoacetonitrile, is prepared by reaction of benzylamine and formaldehyde with the extremely toxic hydrocyanic acid (see also Tetrahedron Letters [23], 27 (1982), 2741-4). The starting material for the synthetic route b), viz. N-benzylglycine, also firstly has to be prepared by reaction of glycine with benzyl chloride or of chloroacetic acid with benzylamine. The reaction of N-benzylaminoacetonitrile or N-benzylglycine as per a) or b) is carried out either by fusion with urea for a long time or by reaction with the toxic cyanic acid. Both methods give 1-benzyl-hydantoin in only low yields: thus, according to Huaxue Shiji 1993, 15(1) 15-16, the reaction of N-benzylglycine (obtained by reaction of benzylarnine with chloroacetic acid) with cyanic acid gives 1-benzylhydantoin in a yield of only 39.5% and the reaction of N-benzylglycine with urea gives 1-benzylhydantoin in a yield of only 45.6%. The subsequent bromination of the 1-benzylhydantoin and treatment with ethanol again proceeds in only a low yield of 42.7%.

反应条件: temp:90.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: To a solution of 92 g (725 mmol) of oxalyl chloride in 188 ml of 1,2-dichlorobenzene are added 26.5 g (145 mmol) of N-benzylaminoacetonitrile. The solution is heated to 60° C. for 20 min and to 90° C. for 6 h. It is allowed to cool and left at this temperature for 15 h. The solvent is removed under reduced pressure and the residue is eluted with silica gel and with a gradient from cyclohexane to 5:1 cyclohexane/ethyl acetate. The product fractions are combined and concentrated to dryness under reduced pressure. The residue is crystallized from diethyl ether. This affords 22 g (60% of theory) of the desired compound. to cool The solvent is removed under reduced pressure the residue is eluted with silica gel and with a gradient from cyclohexane to 5:1 cyclohexane/ethyl acetate concentrated to dryness under reduced pressure The residue is crystallized from diethyl ether

反应条件: temp:90.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: To a solution of 92 g (725 mmol) of oxalyl chloride in 188 ml of 1,2-dichlorobenzene are added 26.5 g (145 mmol) of N-benzylaminoacetonitrile. The solution is heated to 60° C. for 20 min and to 90° C. for 6 h. It is allowed to cool and left at this temperature for 15 h. The solvent is removed under reduced pressure and the residue is eluted with silica gel and with a gradient from cyclohexane to 5:1 cyclohexane/ethyl acetate. The product fractions are combined and concentrated to dryness under reduced pressure. The residue is crystallized from diethyl ether. This affords 22 g (60% of theory) of the desired compound. to cool The solvent is removed under reduced pressure the residue is eluted with silica gel and with a gradient from cyclohexane to 5:1 cyclohexane/ethyl acetate concentrated to dryness under reduced pressure The residue is crystallized from diethyl ether

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: The starting material for the abovementioned synthetic route a), viz. N-benzyl-aminoacetonitrile, is prepared by reaction of benzylamine and formaldehyde with the extremely toxic hydrocyanic acid (see also Tetrahedron Letters [23], 27 (1982), 2741-4). The starting material for the synthetic route b), viz. N-benzylglycine, also firstly has to be prepared by reaction of glycine with benzyl chloride or of chloroacetic acid with benzylamine. The reaction of N-benzylaminoacetonitrile or N-benzylglycine as per a) or b) is carried out either by fusion with urea for a long time or by reaction with the toxic cyanic acid. Both methods give 1-benzyl-hydantoin in only low yields: thus, according to Huaxue Shiji 1993, 15(1) 15-16, the reaction of N-benzylglycine (obtained by reaction of benzylarnine with chloroacetic acid) with cyanic acid gives 1-benzylhydantoin in a yield of only 39.5% and the reaction of N-benzylglycine with urea gives 1-benzylhydantoin in a yield of only 45.6%. The subsequent bromination of the 1-benzylhydantoin and treatment with ethanol again proceeds in only a low yield of 42.7%.

反应条件: temp:90.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: To a solution of 92 g (725 mmol) of oxalyl chloride in 188 ml of 1,2-dichlorobenzene are added 26.5 g (145 mmol) of N-benzylaminoacetonitrile. The solution is heated to 60° C. for 20 min and to 90° C. for 6 h. It is allowed to cool and left at this temperature for 15 h. The solvent is removed under reduced pressure and the residue is eluted with silica gel and with a gradient from cyclohexane to 5:1 cyclohexane/ethyl acetate. The product fractions are combined and concentrated to dryness under reduced pressure. The residue is crystallized from diethyl ether. This affords 22 g (60% of theory) of the desired compound. to cool The solvent is removed under reduced pressure the residue is eluted with silica gel and with a gradient from cyclohexane to 5:1 cyclohexane/ethyl acetate concentrated to dryness under reduced pressure The residue is crystallized from diethyl ether