Sodium Hydroxide → 1-N-acetyl-2-(2-dimethylaminobenzylthio)-5,5-dimethyl-2-imidazolin-4-one

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Reaction Steps

Initially, 4.18g of 2-dimethylaminobenzylchloride hydrochloride was added to a solution of 3.43 g of 1-N-acetyl-5,5-dimethyl-2-thiohydantoin in 50 mL of N,N-dimethylsulfoxide. The reaction mixture was stirred for one hour at the room temperature and poured into 100 mL of water. The pH of the solution was adjusted to 7-8 with a diluted aqueous solution of NaOH and extracted. The precipitate was extracted with 100 mL of ethyl acetate (AcOEt). The thus obtained AcOET layer was successively washed two times with 100 mL of water and 100 mL of brine, dried over magnesium sulfate (MgSO4), and concentrated in vacuo. The thus obtained residue was purified by column chromatography (using CHCL3 as a developing solvent). Recrystallized from diethyl ether-n-hexane gave the desired compound in the form of needle-like crystal. The yield of this compound was 3.4 g with a yield ratio of 57.6%, and the melting point was 99°-100° C.

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