o-(Trifluoromethyl)benzaldehyde → 2-(2-(trifluoromethyl)phenyl)-1H-benzo[d]imidazole-4-carboxylic acid

HRID 85095

Reaction equation

HRID 85095 reaction equation
[NH2:1][C:2]1[C:10]([NH2:11])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[F:12][C:13]([F:23])([F:22])[C:14]1[CH:21]=[CH:20][CH:19]=[CH:18][C:15]=1[CH:16]=O.S(S([O-])=O)([O-])(=O)=O.[Na+].[Na+]>CN(C=O)C.O>[F:12][C:13]([F:22])([F:23])[C:14]1[CH:21]=[CH:20][CH:19]=[CH:18][C:15]=1[C:16]1[NH:11][C:10]2[CH:9]=[CH:8][CH:7]=[C:3]([C:4]([OH:6])=[O:5])[C:2]=2[N:1]=1

Participants

6

Reactant 3

HCID 123067o-(Trifluoromethyl)benzaldehydeHCID 1980692,3-Diaminobenzoic acidHCID 656671Sodium Pyrosulfite

Product 1

HCID 672016022-(2-(trifluoromethyl)phenyl)-1H-benzo[d]imidazole-4-carboxylic acidYield 74.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

2,3-diaminobenzoic acid (1; 50 mg, 0.33 mmol), 2-(trifluoromethyl)benzaldehyde (2; 57 mg, 0.33 mmol), and sodium metabisulfite (Na2S2O5, 82 mg, 0.43 mmol) were taken up in DMF (5 mL) and stirred at 100° C. for 17 h. The reaction mixture was cooled to room temperature and diluted with H2O. The resulting mixture was stirred at room temperature for 1 h and filtered. The collected solids were washed with water and dried to afford 2-(2-(trifluoromethyl)phenyl)-1H-benzo[d]imidazole-4-carboxylic acid 3 as a pale brown solid (75 mg, yield: 74%). MS (ESI) calcd for C15H9F3N2O2: 306.06; found: 307 [M+H].

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. stirringThe resulting mixture was stirred at room temperature for 1 h
  3. filtrationfiltered
  4. washThe collected solids were washed with water
  5. customdried

Sources & evidence

ORD record
ord-b3298b89d23c40499eca393070544e95
Source dataset
uspto-grants-2014_09
Patent number
US08846947B2

Linked notes

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