Acetone → 2-(2-Dimethylaminobenzylmercapto)-1H-thieno[3,4-d]imidazole

HRID 2350861Notes

Reaction equation

HRID 2350861 reaction equation
Br.[CH3:2][N:3]([CH3:12])[C:4]1[CH:11]=[CH:10][CH:9]=[CH:8][C:5]=1[CH2:6]Br.[SH:13][C:14]1[NH:15][C:16]2[C:17](=[CH:19][S:20][CH:21]=2)[N:18]=1.CC(C)=O>CC(N(C)C)=O>[CH3:2][N:3]([CH3:12])[C:4]1[CH:11]=[CH:10][CH:9]=[CH:8][C:5]=1[CH2:6][S:13][C:14]1[NH:18][C:17]2=[CH:19][S:20][CH:21]=[C:16]2[N:15]=1

Participants

5

Reactant 3

HCID 180AcetoneHCID 198473862-(Bromomethyl)-N,N-dimethylaniline hydrobromideHCID 178527818HCID 178527818, compound

Product 1

HCID 141811452-(2-Dimethylaminobenzylmercapto)-1H-thieno[3,4-d]imidazole

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

2.9 g of 2-dimethylaminobenzyl bromide hydrobromide are added to a solution of 1.56 g of 2-mercaptothieno[3,4-d]imidazole in 20 ml of anhydrous dimethylacetamide. A crystalline precipitate separates out in a weakly exothermic reaction. The mixture is stirred at room temperature for one hour, acetone is added, and the crystals are filtered off and dried in a stream of air. The crystalline solid is then introduced into saturated aqueous NaHCO3 solution, the mixture is heated briefly on a steam bath and, after stirring at room temperature, the crystals are filtered off. Treatment with active charcoal in ethanol and concentration is followed by solution being induced to crystallize with a little acetone.

Workup

  1. customA crystalline precipitate separates out in a weakly exothermic reaction
  2. filtrationthe crystals are filtered off
  3. customdried in a stream of air
  4. additionThe crystalline solid is then introduced into saturated aqueous NaHCO3 solution
  5. temperaturethe mixture is heated briefly on a steam bath
  6. stirringafter stirring at room temperature
  7. filtrationthe crystals are filtered off
  8. concentrationTreatment with active charcoal in ethanol and concentration
  9. customto crystallize with a little acetone

Sources & evidence

ORD record
ord-a59278121bbd4263910513c12f79cb59
Source dataset
uspto-grants-1989_10
Patent number
US04871734

Reaction notes

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