2-(chloromethyl)-N,N-dimethylaniline hydrochloride → 4-(2-Dimethylaminobenzylthio)-5,5-dimethyl-3-imidazolin-2-one

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Reaction Steps

Initially, 2.5 g of 2-dimethylaminobenzylchloride hydrochloride was added to a solution of 1.5 g of 5,5-dimethyl-4-thiohydantoin in 50 mL of methanol (MeQH). The reaction mixture was stirred for two hours at the room temperature and concentrated in vacuo. To the residue, there was added 100 mL of CHCl3. The residue was washed two times with 100 mL of aqueous solution of NaHCO3, dried over MgSO4 and concentrated in vacuo. The residue purified by column chromatography [CHCl3 :MeOH=100:1 (v/v)]. Recrystallized from diethyl ether gave the desired compound in the form of needle-like crystal. The yield of this compound was 2 g with a yield ratio of 69.1%, and the melting point was 160°-162° C.

Provenance & Evidence