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

HRID 3241Notes

Reaction equation

HRID 3241 reaction equation
Cl.[CH3:2][N:3]([CH3:12])[C:4]1[CH:11]=[CH:10][CH:9]=[CH:8][C:5]=1[CH2:6]Cl.[CH3:13][C:14]1([CH3:21])[NH:18][C:17](=[O:19])[NH:16][C:15]1=[S:20]>CO>[CH3:2][N:3]([CH3:12])[C:4]1[CH:11]=[CH:10][CH:9]=[CH:8][C:5]=1[CH2:6][S:20][C:15]1[C:14]([CH3:21])([CH3:13])[NH:18][C:17](=[O:19])[N:16]=1

Participants

4

Reactant 2

HCID 135374262-(chloromethyl)-N,N-dimethylaniline hydrochlorideHCID 189348924,4-Dimethyl-5-sulfanylideneimidazolidin-2-one

Product 1

HCID 189348884-(2-Dimethylaminobenzylthio)-5,5-dimethyl-3-imidazolin-2-one

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

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.

Workup

  1. concentrationconcentrated in vacuo
  2. additionTo the residue, there was added 100 mL of CHCl3
  3. washThe residue was washed two times with 100 mL of aqueous solution of NaHCO3
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe residue purified by column chromatography [CHCl3 :MeOH=100:1 (v/v)]
  7. customRecrystallized from diethyl ether

Sources & evidence

ORD record
ord-673e7e0da0374e52b0efea0bb7e74951
Source dataset
uspto-grants-1998_03
Patent number
US05733922

Reaction notes

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