P-Toluenesulfonylhydrazide → Methyl 2-chloro-3-(tosylhydrazono)butanoate

Participants

Reaction Steps

A solution of 25 ml of methyl 2-chloroacetoacetate in 25 ml of THF was added dropwise over 30 minutes to a solution of 37.5 g of tosyl hydrazine in 150 ml of THF. The mixture was allowed to stand overnight, then heated at reflux for 2 hours, cooled to room temperature and stripped of solvent. The residue was then dissolved in 200 ml of ether. Crystallization occurred at room temperature. The collected solids were dried to give methyl 2-chloro-3-(tosylhydrazono)butanoate (7B), as a light yellow solid, m.p.: 97°-101° C.

Provenance & Evidence