Dimethylacetamide → 5-(6-Benzoyl-1H-benzimidazol-2-yl)furan-2-carboxylic acid

HRID 553252Notes

Reaction equation

HRID 553252 reaction equation
CN(C)C(=O)C.[NH2:7][C:8]1[CH:9]=[C:10]([CH:19]=[CH:20][C:21]=1[NH2:22])[C:11]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:12].S([O-])(O)=O.[Na+].[CH:28]([C:30]1[O:34][C:33]([C:35]([OH:37])=[O:36])=[CH:32][CH:31]=1)=O>O>[C:11]([C:10]1[CH:19]=[CH:20][C:21]2[N:22]=[C:28]([C:30]3[O:34][C:33]([C:35]([OH:37])=[O:36])=[CH:32][CH:31]=3)[NH:7][C:8]=2[CH:9]=1)(=[O:12])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

6

Reactant 4

HCID 31374DimethylacetamideHCID 1355203,4-DiaminobenzophenoneHCID 27937195-Formyl-2-furancarboxylic AcidHCID 23665763Sodium Bisulfite

Product 1

HCID 579557865-(6-Benzoyl-1H-benzimidazol-2-yl)furan-2-carboxylic acidYield 64%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

N,N-Dimethylacetamide (5 ml) was heated to 130° C., and 3,4-diaminobenzophenone (63 mg, 0.30 mmol) and sodium hydrogensulfite (37 mg, 0.36 mmol) were added and the mixture was stirred for 5 minutes. 5-Formyl-furan-2-carboxylic acid (50 mg, 0.36 mmol) was added and stirred at 130° C. for 1.5 hours. The reaction mixture was allowed to cool to room temperature with stirring, and after addition of water to reaction mixture, precipitate was collected by filtration to afford 5-(5-benzoylbenzimidazol-2-yl)-furan-2-carboxylic acid (63 mg, 64%) as a pale yellow solid.

Workup

  1. stirringstirred at 130° C. for 1.5 hours
  2. stirringwith stirring
  3. customto reaction mixture, precipitate
  4. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-f2d7cbdf9ce447d0b825c09eadf05de5
Source dataset
uspto-grants-2011_05
Patent number
US07951956B2

Reaction notes

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