Water → Methyl 5-[[[1-methyl-2-(phenylmethylene)hydrazino](methylthio)methylene]amino]-5-oxopentanoate

Participants

Reaction Conditions

Reaction Steps

Methyl 4-(chloroformyl)butyrate (31.2 g) was added dropwise during 1 h at 20° to a stirred solution of methyl 1-methyl-2-(phenylmethylene)hydrazine carboximidothioate (3.60 g) and triethylamine (20.0 g) in dichloromethane (100 ml). The pale yellow suspension was stirred at 20° C. for 16 h. A further portion of methyl 4-(chloroformyl)butyrate (6.2 g) and triethylamine (4.0 g) was added and stirring continued for a further 1 h. Water (100 ml) was added, the organic layer separated and washed successively with saturated aqueous sodium bicarbonate and water, dried, and evaporated to give a brown solid (53.6 g). This solid was recrystallised from ether to give the title compound (30.9 g) as a pale yellow solid m.p. 69°-70°.

Provenance & Evidence