Pyrrole-2-carboxaldehyde → 920286-48-2

HRID 553244Notes

Reaction equation

HRID 553244 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[NH:31][CH:32]=[CH:33][CH:34]=1)=O>O>[C:11]([C:10]1[CH:19]=[CH:20][C:21]2[N:22]=[C:28]([C:30]3[NH:31][CH:32]=[CH:33][CH:34]=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 13854Pyrrole-2-carboxaldehydeHCID 31374DimethylacetamideHCID 1355203,4-DiaminobenzophenoneHCID 23665763Sodium Bisulfite

Product 1

HCID 135962680920286-48-2Yield 63%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

N,N-Dimethylacetamide (5 ml) was heated to 130° C., and 3,4-diaminobenzophenone (150 mg, 0.71 mol) and sodium hydrogensulfite (89 mg, 0.85 mol) were added and stirred for 5 minutes. 2-Formyl-pyrrole (81 mg, 0.85 mol) 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-benzoyl-2-(pyrrol-2-yl)-benzimidazole (129 mg, 63%) 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-ddada5405fd844bf855daa1e697a528b
Source dataset
uspto-grants-2011_05
Patent number
US07951956B2

Reaction notes

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