Ethylenediamine → N-methyl-N'-[2-((5-benzyl-4-oxazolyl)methylamino)ethyl]thiourea

Participants

Reaction Steps

5-Benzyl-4-oxazolecarboxylic acid is converted to 5-benzyl-4-hydroxymethyl xazole by the procedure of Example 135. Treating this hydroxy ethyl compound with thionyl chlroide gives 5-benzyl-4-chloromethyloxazole. Reacting ethylenediamine with 5-benzyl-4-chloro-methyloxazole by the procedure of Example 34, then reacting the resulting N-(5-benzyl-4-oxazolylmethyl)ethylenediamine with methyl isothiocyanate by the procedure of Example 3(b) and chromatographing gives N-methyl-N'-[2-((5-benzyl-4-oxazolyl)methylamino)ethyl]-thiourea. Reacting this thiourea with lead cyanamide by the procedure of Example 3(b) gives N-[2-((5-benzyl-4-oxazolyl)methylamino)ethyl]-N'-cyano-N"-methylguanidine.

Provenance & Evidence