2-(chloromethyl)-N,N-dimethylaniline hydrochloride → 2-benzylthio-4-(2-dimethylaminobenzylthio)-5,5-dimethyl-5H-imidazole

HRID 3252Notes

Reaction equation

HRID 3252 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.[CH2:13]([S:20][C:21]1[NH:22][C:23]([CH3:28])([CH3:27])[C:24](=[S:26])[N:25]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>C(O)C>[CH2:13]([S:20][C:21]1[N:25]=[C:24]([S:26][CH2:6][C:5]2[CH:8]=[CH:9][CH:10]=[CH:11][C:4]=2[N:3]([CH3:12])[CH3:2])[C:23]([CH3:28])([CH3:27])[N:22]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

4

Reactant 2

HCID 135374262-(chloromethyl)-N,N-dimethylaniline hydrochlorideHCID 178418227HCID 178418227, compound

Product 1

HCID 189348372-benzylthio-4-(2-dimethylaminobenzylthio)-5,5-dimethyl-5H-imidazole

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Initially, 0.65 g of 2-dimethylaminobenzylchloride hydrochloride was added to a solution of 0.7 g of 2-benzylthio-5,5-dimethylimidazolin-4-thione in 20 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-4-(2-dimethylaminobenzylthio)-5,5-dimethyl-5H-imidazole in the form of a needle-like crystal. The yield of this compound was 0.75 g with a yield ratio of 72.2%, and the melting point was 91°-92° C.

Workup

  1. concentrationconcentrated in vacuo
  2. additionThe residue was treated
  3. custompurified by column chromatography (CHCl3)
  4. customRecrystallization from diethyl ether-n-hexane

Sources & evidence

ORD record
ord-9a24f90cc7884da083a28d124bc01ed8
Source dataset
uspto-grants-1998_03
Patent number
US05733922

Reaction notes

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