o-(Trifluoromethyl)benzaldehyde → HCID 67203503, compound

HRID 85147Notes

Reaction equation

HRID 85147 reaction equation
[NH2:1][C:2]1[C:10]([NH2:11])=[CH:9][C:8]([O:12][CH3:13])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[F:14][C:15]([F:25])([F:24])[C:16]1[CH:23]=[CH:22][CH:21]=[CH:20][C:17]=1[CH:18]=O.S(S([O-])=O)([O-])(=O)=O.[Na+].[Na+]>CN(C=O)C.O>[CH3:13][O:12][C:8]1[CH:7]=[C:3]([C:4]([OH:6])=[O:5])[C:2]2[N:1]=[C:18]([C:17]3[CH:20]=[CH:21][CH:22]=[CH:23][C:16]=3[C:15]([F:14])([F:24])[F:25])[NH:11][C:10]=2[CH:9]=1

Participants

6

Reactant 3

HCID 123067o-(Trifluoromethyl)benzaldehydeHCID 656671Sodium PyrosulfiteHCID 58279044HCID 58279044, compound

Product 1

HCID 67203503HCID 67203503, compoundYield 40%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 2,3-diamino-5-methoxybenzoic acid 86 (1.1 equiv) and 2-(trifluoromethyl)benzaldehyde 74 (1 equiv) and sodium metabisulfite (3 equiv) in DMF was stirred under reflux for 12 h. Upon cooling to room temperature, the reaction mixture was diluted with water. The resulting solids were collected by filtration and dried to afford 6-methoxy-2-(2-(trifluoromethyl)phenyl)-1H-benzo[d]imidazole-4-carboxylic acid 87 as dark yellow solid (40%).

Workup

  1. temperatureunder reflux for 12 h
  2. filtrationThe resulting solids were collected by filtration
  3. customdried

Sources & evidence

ORD record
ord-255f94cbd71c401ea87af6038a02ec98
Source dataset
uspto-grants-2014_09
Patent number
US08846947B2

Reaction notes

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