Water → 2-(2,6-Dichloro-phenyl)-3H-benzoimidazole-5-carboxylic acid methyl ester

HRID 1513229Notes

Reaction equation

HRID 1513229 reaction equation
[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]([NH2:10])=[C:6]([NH2:11])[CH:5]=1.[Cl:13][C:14]1[CH:21]=[CH:20][CH:19]=[C:18]([Cl:22])[C:15]=1[CH:16]=O.O.OOS([O-])=O.[K+]>CN(C=O)C.CCOC(C)=O>[CH3:1][O:2][C:3]([C:4]1[CH:9]=[CH:8][C:7]2[N:10]=[C:16]([C:15]3[C:14]([Cl:13])=[CH:21][CH:20]=[CH:19][C:18]=3[Cl:22])[NH:11][C:6]=2[CH:5]=1)=[O:12]

Participants

7

Reactant 4

HCID 962WaterHCID 67372,6-DichlorobenzaldehydeHCID 1355243,5-Diamino-2-methylbenzoic acidHCID 23707502Potassium hydroxy sulfite

Product 1

HCID 669663062-(2,6-Dichloro-phenyl)-3H-benzoimidazole-5-carboxylic acid methyl ester

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3,4-diaminobenzoic acid methyl ester (3.32 g, 20 mmol) and 2,6-dichlorobenzaldehyde (3.5 g, 20 mmol) in DMF (20 mL)+water (2 mL) was added oxone (2.46 g, 4 mmol). The mixture was stirred at RT for 18 h then EtOAc was added. The mixture was washed with water and brine then was dried over sodium sulfate. The solvent was removed under reduced pressure to give the title compound as a yellow solid.

Workup

  1. washThe mixture was washed with water and brine
  2. dry with materialthen was dried over sodium sulfate
  3. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-1a99f94ffd014bd9a19cba4932a4c7c8
Source dataset
uspto-grants-2012_07
Patent number
US08217065B2

Reaction notes

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