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

HRID 1360734
Notes
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Reaction equation

HRID 1360734 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
ParticipantsProcedureWorkupSources & evidenceReaction notes

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-51180d61d80240ba957d2b1a9bbdfbab
Source dataset
uspto-grants-2011_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07879850B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes