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

HRID 621542Notes

Reaction equation

HRID 621542 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-9ec864d5187649bda4675fc3b8d64f5e
Source dataset
uspto-grants-1989_04
Patent number
US04824856

Reaction notes

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