2-Methoxyacetohydrazide → 1-(methoxymethyl)-6-phenyl-8-chloro-4H-s-triazolo[4,3-a][1,4]benzodiazepine
Reaction equation
CS[C:3]1[CH2:9][N:8]=[C:7]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:6]2[CH:16]=[C:17]([Cl:20])[CH:18]=[CH:19][C:5]=2[N:4]=1.[CH3:21][O:22][CH2:23][C:24]([NH:26][NH2:27])=O>CN(C)P(=O)(N(C)C)N(C)C>[CH3:21][O:22][CH2:23][C:24]1[N:4]2[C:5]3[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][C:6]=3[C:7]([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)=[N:8][CH2:9][C:3]2=[N:27][N:26]=1Participants
4
Procedure
A solution of 10.0 g of 2-(methylthio)-5-phenyl-7-chloro-3H-1,4-benzodiazepine and 4.85 g of 2-methoxyacetic acid hydrazide (cp. E. J. Browne and J. B. Polya, J.Chem.Soc. 1962, 5149-5152) in 70 ml of abs. hexamethylphosphoric acid triamide is heaated for 11 hours at 140°. The solvent is then distilled off in vacuo. The residue is taken up in methylene chloride; the solution is washed with water and then with saturated sodium chloride solution, dried over sodium sulphate, and concentrated by evaporation. Crystallisation of the concentration residue from ethyl acetate/petroleum ether yields 1-(methoxymethyl)-6-phenyl-8-chloro-4H-s-triazolo[4,3-a][1,4]benzodiazepine, M.P. 185°-191°. After chromatography of the mother liquor on 100 g of silica gel "Merck", a further amount of final product of the same melting point can be isolated.