Reacción #3333

Ecuación de reacción

sodium hydroxide

2-dimethylaminobenzylchloride hydrochloride

5,5-dimethyl-2-thiohydantoin

water

→

desired compound

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

Disolventes

dimethylsulfoxide

Condiciones de reacción

Tratamiento posterior

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

Procedimiento

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.

Fuente