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

HRID 1360732
Notes
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Reaction equation

HRID 1360732 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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 6228
Dimethylformamide
Solvent
HCID 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-93dec51370464b599102a3fc45193cf3
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