5,5-Dimethyl-2,4-imidazolidinedithione → 2,4-bis(3-dimethylaminobenzylthio)-5,5-dimethyl-5H-imidazole

HRID 3247Notes

Reaction equation

HRID 3247 reaction equation
Cl.[CH3:2][N:3]([CH3:12])[C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][CH:11]=1)[CH2:7]Cl.[CH3:13][C:14]1([CH3:21])[NH:18][C:17](=[S:19])[NH:16][C:15]1=[S:20].C[O-].[Na+]>CO>[CH3:2][N:3]([CH3:12])[C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][CH:11]=1)[CH2:7][S:19][C:17]1[N:16]=[C:15]([S:20][CH2:7][C:6]2[CH:9]=[CH:10][CH:11]=[C:4]([N:3]([CH3:12])[CH3:2])[CH:5]=2)[C:14]([CH3:21])([CH3:13])[N:18]=1

Participants

5

Reactant 3

HCID 30021425,5-Dimethyl-2,4-imidazolidinedithioneHCID 10942334Sodium MethoxideHCID 189348953-(chloromethyl)-N,N-dimethylaniline hydrochloride

Product 1

HCID 189349022,4-bis(3-dimethylaminobenzylthio)-5,5-dimethyl-5H-imidazole

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Initially, 2.94 g of 3-dimethylaminobenzylchloride hydrochloride was added to a mixture of 1.6 g of 5,5-dimethyl-2,4-dithiohydantoin and 1.3 g of sodium methoxide in 50 mL of methanol (MeOH). 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 56, and chromatographed on a column of silica gel (CHCl3). From the earlier fractions, 2,4-bis(3-dimethylaminobenzylthio)-5,5-dimethyl-5H-imidazole was isolated, in the form of a syrup. The yield of this compound was 0.31 g with a yield ratio of 7.4%.

Workup

  1. concentrationconcentrated in vacuo
  2. additionThe residue was treated
  3. customchromatographed on a column of silica gel (CHCl3)

Sources & evidence

ORD record
ord-483dd6c046dd4bfda158d9c42f0f2afc
Source dataset
uspto-grants-1998_03
Patent number
US05733922

Reaction notes

Loading…