1,1-Dimethylhydrazine → 1,1-Dimethyl-4-(O-tolyl)semicarbazide

Participants

Reaction Conditions

Reaction Steps

o-Tolyl isocyanate (10.0 g) was dissolved in 75 mL of toluene under nitrogen. The solution was cooled to 5° C. and to this was slowly added a solution of 1,1-dimethylhydrazine (5.7 mL) in toluene. After addition, the ice-bath was removed and the resulting slurry was allowed to stir an additional 10 minutes. The solid was filtered off and rinsed successively with hexane, a small amount of 20% diethyl ether/hexane, and then hexanes again. This afforded 11.1 g (77%) of the title compound of Step A. 1H NMR (CDCl3): δ 8.1 (br s,1H), 7.94 (d,1H), 7.21-7.15 (m,3H), 6.99 (t,1H), 5.23 (br s,1H), 2.63 (s,6H), 2.27 (s,3H).

Provenance & Evidence