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

HRID 3249

Reaction equation

HRID 3249 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, 3.1 g of 3-dimethylaminobenzylchloride hydrochloride was added to a mixture of 0.8 g of 5,5-dimethyl-2,4-dithiohydantoin and 1.34 g of sodium methoxide in 50 mL of methanol (MeOH). The reaction mixture was treated following the procedure used in Example 56, and purified by column chromatograph (CHCl3) to give the desired compound in the form of a syrup. The yield of this compound was 1.65 g with a yield ratio of 82.9%.

Workup

  1. additionThe reaction mixture was treated
  2. custompurified by column chromatograph (CHCl3)

Sources & evidence

ORD record
ord-1ddb24d2ec1c4eb5b7c0603a217b4d61
Source dataset
uspto-grants-1998_03
Patent number
US05733922

Linked notes

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