2-(chloromethyl)-N,N-dimethylaniline hydrochloride → Benzenamine, 2-[(1H-benzimidazol-2-ylthio)methyl]-N,N-dimethyl-

HRID 487036Notes

Reaction equation

HRID 487036 reaction equation
[SH:1][C:2]1[NH:3][C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=1.Cl.[CH3:12][N:13]([CH3:22])[C:14]1[CH:21]=[CH:20][CH:19]=[CH:18][C:15]=1[CH2:16]Cl>C(O)C>[CH3:12][N:13]([CH3:22])[C:14]1[CH:21]=[CH:20][CH:19]=[CH:18][C:15]=1[CH2:16][S:1][C:2]1[NH:3][C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=1

Participants

4

Reactant 2

HCID 135374262-(chloromethyl)-N,N-dimethylaniline hydrochlorideHCID 178527775HCID 178527775, compound

Product 1

HCID 10265859Benzenamine, 2-[(1H-benzimidazol-2-ylthio)methyl]-N,N-dimethyl-Yield 63.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-Mercaptobenzimidazole (4.73 g) was dissolved in 150 ml of ethanol, and to the solution was added 6.18 g of 2-dimethylaminobenzyl chloride hydrochloride. The mixture was stirred at room temperature for 30 minutes. Precipitated crystals were collected by filtration. A saturated aqueous NaHCO3 solution was added to the crystals, and the resulting mixture was extracted with chloroform. The chloroform layer was washed with saturated brine and then dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure and the residue was recrystallized from a mixture of chloroform and acetonitrile to obtain 5.39 g of 2-(2-dimethylaminobenzylthio)benzimidazole as a colorless crystalline product (m.p. 164° C.).

Workup

  1. customPrecipitated crystals
  2. filtrationwere collected by filtration
  3. additionA saturated aqueous NaHCO3 solution was added to the crystals
  4. extractionthe resulting mixture was extracted with chloroform
  5. washThe chloroform layer was washed with saturated brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. distillationThe solvent was distilled off under reduced pressure
  8. customthe residue was recrystallized from a mixture of chloroform and acetonitrile

Sources & evidence

ORD record
ord-70099661023c4d8cbb26ac852174275d
Source dataset
uspto-grants-1994_03
Patent number
US05294439

Reaction notes

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