Dimethylamine → HCID 20508554, compound

Participants

Reaction Steps

To a solution of [6-(o-chlorophenyl)-4H-s-triazolo[4,3-a][1,4]benzodiazepin-8-yl]isocyanate, prepared as described in paragraph (a) of Example 1 from 7.0 g (22.6 mmol) of 8-amino-6-(o-chlorophenyl)-4H-s-triazolo[4,3-a][1,4]benzodiazepine, but using methylene chloride in place of 1,2-dichloroethane, is added in one portion while cooling with ice and stirring a suspension of 8.7 g (81.9 mmol) of sodium carbonate in 5.3 g (117.8 mmol) of dimethylamine and 50 ml of 1,2-dichloroethane. The mixture is left for 25 hours at room temperature and then evaporated at 50° C. in vacuo. The residue is suspended in 300 ml of water, extracted four times with methylene chloride/ethanol (4:1) and the combined organic extracts are subsequently dried and evaporated. Crystallisation from methylene chloride/ethyl acetate yields 3-[6-(o-chlorophenyl)-4H-s-triazolo[4,3-a][1,4]benzodiazepin-8-yl]-1,1-dimethylurea of melting point 180° C. (decomposition).

Provenance & Evidence