5,5-Dimethyl-2,4-imidazolidinedithione → 2,4-bis(2-dimethylaminobenzylthio)-5,5-dimethyl-5H-imidazole

HRID 3244Notes

Reaction equation

HRID 3244 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](=[S:19])[NH:16][C:15]1=[S:20]>CCO>[CH3:2][N:3]([CH3:12])[C:4]1[CH:11]=[CH:10][CH:9]=[CH:8][C:5]=1[CH2:6][S:19][C:17]1[N:16]=[C:15]([S:20][CH2:6][C:5]2[CH:8]=[CH:9][CH:10]=[CH:11][C:4]=2[N:3]([CH3:12])[CH3:2])[C:14]([CH3:21])([CH3:13])[N:18]=1

Participants

4

Reactant 2

HCID 30021425,5-Dimethyl-2,4-imidazolidinedithioneHCID 135374262-(chloromethyl)-N,N-dimethylaniline hydrochloride

Product 1

HCID 189348482,4-bis(2-dimethylaminobenzylthio)-5,5-dimethyl-5H-imidazole

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

Initially, a solution of 9.1 g of 2-dimethylaminobenzylchloride hydrochloride in 50 mL of EtOH was added to a solution of 7 g of 5,5-dimethyl-2,4-dithiohydantoin in 100 mL of ethanol (EtOH). The reaction mixture was stirred for 1.5 hour at the room temperature and concentrated in vacuo. To the residue, there was added 100 mL of chloroform (CHCl3). The residue was then washed with an aqueous solution of potassium carbonate (CaCO3), dried over magnesium sulfate (MgSO4), and concentrated in vacuo. The residue was chromatographed on a column of silica gel (CHCl3). From the earlier fractions, 2,4-bis(2-dimethylaminobenzylthio)-5,5-dimethyl-5H-imidazole was isolated as a syrup. The yield of this compound was 1.1 g with a yield ratio of 5.9%.

Workup

  1. concentrationconcentrated in vacuo
  2. additionTo the residue, there was added 100 mL of chloroform (CHCl3)
  3. washThe residue was then washed with an aqueous solution of potassium carbonate (CaCO3)
  4. dry with materialdried over magnesium sulfate (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customThe residue was chromatographed on a column of silica gel (CHCl3)

Sources & evidence

ORD record
ord-a4c2572338d149fc9b4505fc6cb945cf
Source dataset
uspto-grants-1998_03
Patent number
US05733922

Reaction notes

Loading…