Thionyl Chloride → HCID 19094217, compound

HRID 487190Notes

Reaction equation

HRID 487190 reaction equation
[CH2:1]([C:5]1[N:9]([CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[Cl:17])[C:8]2[C:18]([CH2:22]O)=[CH:19][CH:20]=[CH:21][C:7]=2[N:6]=1)[CH2:2][CH2:3][CH3:4].S(Cl)([Cl:26])=O>C(Cl)Cl>[CH2:1]([C:5]1[N:9]([CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[Cl:17])[C:8]2[C:18]([CH2:22][Cl:26])=[CH:19][CH:20]=[CH:21][C:7]=2[N:6]=1)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 19094244HCID 19094244, compound

Product 1

HCID 19094217HCID 19094217, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 2-n-butyl-1-(2-chlorophenyl)methyl-7-hydroxymethyl-1H-benzimidazole (1.01 g, 2.76 mmol) in methylene chloride (50 mL) was added thionyl chloride (0.61 mL). The resulting solution was stirred at ambient temperature for one hour, the solvent was evaporated, the residue triturated with toluene and then petroleum ether, and the white crystals (1.06 g) of 2-n-butyl-7-chloromethyl-1-(2-chlorophenyl)methyl-1H-benzimidazole were isolated and washed well with ether to give the title compound as the hydrochloride salt; mp 180°-184° C.

Workup

  1. customthe solvent was evaporated
  2. customthe residue triturated with toluene

Sources & evidence

ORD record
ord-230dae8544604c3e9565059c23bac549
Source dataset
uspto-grants-1994_03
Patent number
US05294631

Reaction notes

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