Dimethylformamide → 2-(2,6-dichlorophenyl)-3H-benzimidazole-5-carbonyl chloride hydrochloride

HRID 1513231Notes

Reaction equation

HRID 1513231 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[C:9]1[NH:10][C:11]2[CH:17]=[C:16]([C:18]([OH:20])=O)[CH:15]=[CH:14][C:12]=2[N:13]=1.CN(C=O)C.C(Cl)[Cl:27]>S(Cl)(Cl)=O>[ClH:1].[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[C:9]1[NH:10][C:11]2[CH:17]=[C:16]([C:18]([Cl:27])=[O:20])[CH:15]=[CH:14][C:12]=2[N:13]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 6344DichloromethaneHCID 433492922-(2,6-Dichloro-phenyl)-3H-benzoimidazole-5-carboxylic acid

Product 1

HCID 866328172-(2,6-dichlorophenyl)-3H-benzimidazole-5-carbonyl chloride hydrochloride

Reagents, catalysts & solvents 1

HCID 24386Thionyl ChlorideSolvent

Procedure

A mixture of 2-(2,6-dichlorophenyl)-3H-benzoimidazole-5-carboxylic acid (5 g) in thionyl chloride (10 mL) containing a catalytic quantity of DMF was stirred at RT for 18 h. Methylene chloride was added and the resulting solid was filtered, washed with methylene chloride and dried under reduced pressure to give the title compound as an off-white solid.

Workup

  1. filtrationthe resulting solid was filtered
  2. washwashed with methylene chloride
  3. customdried under reduced pressure

Sources & evidence

ORD record
ord-78761b67b12c4165bc29b54f448b2fd3
Source dataset
uspto-grants-2012_07
Patent number
US08217065B2

Reaction notes

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