2,3-Dimethylbenzaldehyde → 2-(2,3-dimethylphenyl)-3H-benzoimidazole-5-carboxylic acid (3,4-dimethylphenyl)-amide

HRID 1514891Notes

Reaction equation

HRID 1514891 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:16]=[CH:17][C:18]=1[NH2:19])[C:5]([NH:7][C:8]1[CH:13]=[CH:12][C:11]([CH3:14])=[C:10]([CH3:15])[CH:9]=1)=[O:6].[CH3:20][C:21]1[C:28]([CH3:29])=[CH:27][CH:26]=[CH:25][C:22]=1[CH:23]=O.C(S([O-])(=O)=O)(F)(F)F.C(S([O-])(=O)=O)(F)(F)F.C(S([O-])(=O)=O)(F)(F)F.[Yb+3]>CS(C)=O>[CH3:15][C:10]1[CH:9]=[C:8]([NH:7][C:5]([C:4]2[CH:16]=[CH:17][C:18]3[N:19]=[C:23]([C:22]4[CH:25]=[CH:26][CH:27]=[C:28]([CH3:29])[C:21]=4[CH3:20])[NH:1][C:2]=3[CH:3]=2)=[O:6])[CH:13]=[CH:12][C:11]=1[CH3:14]

Participants

5

Reactant 3

HCID 342242,3-DimethylbenzaldehydeHCID 2733225Ytterbium triflate2×HCID 66965643HCID 66965643, compound

Product 1

HCID 669661432-(2,3-dimethylphenyl)-3H-benzoimidazole-5-carboxylic acid (3,4-dimethylphenyl)-amide

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of 3,4-diamino-N-(3,4-dimethylphenyl)-benzamide (71 mg) and 2,3-dimethylbenzaldehyde (34 mg) in DMSO (1 mL) was added Yb(OTf)3 and the mixture was stirred at room temperature for 4 h. Additional Yb(OTf)3 was added and stirring was continued until starting material was consumed. Water was added and the mixture was extracted with EtOAc. The organic phase was washed with water and dried over sodium sulfate. The solvent was removed under reduced pressure and the residue was purified by flash chromatography using CH2Cl2/EtOAc (2:1) as eluent to furnish 2-(2,3-dimethylphenyl)-3H-benzoimidazole-5-carboxylic acid (3,4-dimethylphenyl)-amide as a beige solid, MS (m/z) 370 (M−1).

Workup

  1. stirringstirring
  2. customwas consumed
  3. additionWater was added
  4. extractionthe mixture was extracted with EtOAc
  5. washThe organic phase was washed with water
  6. dry with materialdried over sodium sulfate
  7. customThe solvent was removed under reduced pressure
  8. customthe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-08438196a75346849b3592f7ba6cd598
Source dataset
uspto-grants-2012_07
Patent number
US08222248B2

Reaction notes

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