5,5-Dimethyl-2,4-imidazolidinedithione → HCID 178418313, compound

HRID 3245Notes

Reaction equation

HRID 3245 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]>C(Cl)(Cl)Cl>[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[NH:18][C:14]([CH3:21])([CH3:13])[C:15](=[S:20])[N:16]=1

Participants

4

Reactant 2

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

Product 1

HCID 178418313HCID 178418313, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Initially, 11 g of 2-dimethylaminobenzylchloride hydrochloride was added to a solution of 8 g of 5,5-dimethyl-2,4-dithiohydantoin in 200 mL of chloroform (CHCl3) at about 60° C. The reaction mixture was stirred for 30 minutes and washed with an aqueous solution of NaHCO3, dried over MgSO4, and concentrated in vacuo. The residue was treated following the procedure used for the compound (a). As a result, the desired compound of 2-(2-dimethylaminobenzylthio)-5,5-dimethylimidazolin-4-thione was isolated by column chromatography. The yield of this compound was 9.1 g with a yield ratio of 62.1%. Further, the desired compound of 2,4-bis(2-dimethylaminobenzylthio)-5,5-dimethyl-5H-imidazole was isolated. The yield of this compound was 1.2 g with a yield ratio of 5.6%.

Workup

  1. washwashed with an aqueous solution of NaHCO3
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated in vacuo
  4. additionThe residue was treated

Sources & evidence

ORD record
ord-5666a9282ea5444b92b3aab759b61587
Source dataset
uspto-grants-1998_03
Patent number
US05733922

Reaction notes

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