2-Propenoic acid, 2-cyano-3-ethoxy-, ethyl ester → ethyl 3-(N'-benzylidene-N-methylhydrazino)2-cyanoacrylate

Participants

Reaction Steps

258 g (1.92 mol) of N-benzylidene-/V′-methylhydrazine and 325 g (1.92 mol) of ethyl ethoxy-methylenecyanoacetate were initially charged in 1000 ml of toluene and heated at the boil for 1 hour. After cooling, the mixture was filtered off with suction, which gave 447 g (89.5% of theory) of ethyl 3-(N′-benzylidene-N-methylhydrazino)-2-cyanoacrylate [log P (pH 2.3)=2.31]. The filtrate was allowed to stand for 16 hours and then again filtered off with suction, which gave another 7.7 g (1.5% of theory) of the desired product.

Provenance & Evidence