Thionyl Chloride → 1h-Benzimidazole,6-(chloromethyl)-1-[(2-chlorophenyl)methyl]-2-methyl-,hydrochloride

HRID 1276897Notes

Reaction equation

HRID 1276897 reaction equation
S(Cl)([Cl:3])=O.[Cl:5][C:6]1[CH:24]=[CH:23][CH:22]=[CH:21][C:7]=1[CH2:8][N:9]1[C:13]2[CH:14]=[C:15]([CH2:18]O)[CH:16]=[CH:17][C:12]=2[N:11]=[C:10]1[CH3:20]>>[ClH:3].[Cl:5][C:6]1[CH:24]=[CH:23][CH:22]=[CH:21][C:7]=1[CH2:8][N:9]1[C:13]2[CH:14]=[C:15]([CH2:18][Cl:3])[CH:16]=[CH:17][C:12]=2[N:11]=[C:10]1[CH3:20]

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 183155381h-Benzimidazole-6-methanol,1-[(2-chlorophenyl)methyl]-2-methyl-

Product 1

HCID 226203411h-Benzimidazole,6-(chloromethyl)-1-[(2-chlorophenyl)methyl]-2-methyl-,hydrochloride

Procedure

Five milliliters of thionyl chloride were added to 3.56 g of 1-(2-chlorobenzyl)-6-hydroxymethyl-2-methylbenzimidazole, and the mixture was stirred at room temperature for 20 minutes and then at 80° C. for 20 minutes. After excess thionyl chloride was distilled off under reduced pressure, the residue was dissolved in 10 ml of chloroform, and the solution was crystallized from hexane. The crystals were separated through filtration, washed with hexane, and dried to give 4.07 g of 1-(2-chlorobenzyl)-6-chloromethyl-2-methylbenzimidazole hydrochloride.

Workup

  1. waitat 80° C. for 20 minutes
  2. distillationAfter excess thionyl chloride was distilled off under reduced pressure
  3. dissolutionthe residue was dissolved in 10 ml of chloroform
  4. customthe solution was crystallized from hexane
  5. customThe crystals were separated through filtration
  6. washwashed with hexane
  7. customdried

Sources & evidence

ORD record
ord-1c878082e4884f07a3867e8d34a67d1a
Source dataset
uspto-grants-2000_12
Patent number
US06166219

Reaction notes

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