Реакция #3333

Уравнение реакции

sodium hydroxide

2-dimethylaminobenzylchloride hydrochloride

5,5-dimethyl-2-thiohydantoin

water

→

desired compound

2-(2-dimethylaminobenzylthio)-5,5-dimethylimidazolin-4-one

Растворители

dimethylsulfoxide

Условия реакции

Обработка

1. 1
   ЭкстракцияA precipitated sediment was extracted from the liquid, two times
2. 2
   ПромывкаThe AcOEt layer was successively washed with 50 mL of water and 50 mL of brine
3. 3
   Сушкаdried over magnesium sulfate (MgSO4)
4. 4
   Концентрированиеconcentrated in vacuo
5. 5
   ДругоеThe thus obtained residue was purified by column chromatography [developing solvent=CHCl3 :MeOH=20:1 (volume ratio, v/v)]
6. 6
   ДругоеRecrystallized from diethyl ether

Методика

Initially, 1 g of 5,5-dimethyl-2-thiohydantoin was dissolved in 20 mL of dimethylsulfoxide, and 1.7 g of 2-dimethylaminobenzylchloride hydrochloride was added to the solution. The reaction mixture was stirred at the room temperature for one hour, and poured into 50 mL of water. The pH value of the solution was adjusted to 7-8 with diluted aqueous solution of 2N sodium hydroxide (NaOH). A precipitated sediment was extracted from the liquid, two times, using 50 mL of ethyl acetate (AcOEt). The AcOEt layer was successively washed with 50 mL of water and 50 mL of brine, dried over magnesium sulfate (MgSO4), and concentrated in vacuo. The thus obtained residue was purified by column chromatography [developing solvent=CHCl3 :MeOH=20:1 (volume ratio, v/v)]. Recrystallized from diethyl ether gave the desired compound in the form of needle-like crystal. The yield of the compound was 1.2 g with a yield ratio of 62.4%, and its melting point was 113°-115° C.

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