Hydrazine hydrate (1:1) → 4-[alpha-Amino-4-chloro-alpha-(o-chlorophenyl)-o-tolyl]-3-[(dimethylamino)methyl]-5-methyl-4h-1,2,4-triazole

Participants

Reaction Steps

A solution of 7.38 g. of 8-chloro-6-(o-chlorophenyl)-1-(dimethylamino)methyl-4H-s-triazolo[4,3 -a][1,4] benzodiazepine (III) (20.0 mmol.) and 5.0 ml. of hydrazine hydrate in 50 ml. of diethylene glycol is heated to about 140° C. for about 18 hours. The reaction is quenched in a cold aqueous 5% sodium hydroxide solution, and the product extracted with chloroform. The extracts are dried and concentrated in vacuo to yield 8.5 g. of oil, which is crystallized from ethyl acetate/hexane mixtures to give 4.0 g. of 4-[α-amino-4-chloro-α-(o-chlorophenyl)-o-tolyl]-3-[(dimethylamino)methyl]-5-methyl-4H-1,2,4 -triazole (I), isomer A, m.p. 142°-144° C., an analytical sample of which melts at 148°-150° C. and has infrared (mull) spectral absorptions at 3380, 3270, 3200, 3070, 2770, 1610, 1590, 1570, 1530 and 1520 cm-1.

Provenance & Evidence