Reaction #3347

Reaction equation

benzylbromide

5,5-dimethyl-2,4-dithiohydantoin

→

2-benzylthio-5,5-dimethylimidazolin-4-thione

Solvents

ethanol

Conditions

Workup

1. 1
   Concentrationconcentrated in vacuo
2. 2
   workup.ADDITIONThe residue was treated
3. 3
   Otherpurified by column chromatography (CHCl3)
4. 4
   OtherRecrystallization from diethyl ether-n-hexane

Procedure

Initially, 1.91 mL of benzylbromide was added to a solution of 1.6 g of 5,5-dimethyl-2,4-dithiohydantoin in 50 mL of ethanol (EtOH). The reaction mixture was stirred at the room temperature for one hour, and concentrated in vacuo. The residue was treated following the procedure used in Example 62, and purified by column chromatography (CHCl3). Recrystallization from diethyl ether-n-hexane gave 2-benzylthio-5,5-dimethylimidazolin-4-thione in the form of a needle-like crystal. The yield of this compound was 0.87 g with a yield ratio of 34.8%, and the melting point was 133°-134° C.

Source