Benzaldehyde → 1H-Benzimidazole, 1,2-diphenyl-

HRID 383205Notes

Reaction equation

HRID 383205 reaction equation
[C:1]1([NH:7][C:8]2[C:9]([NH2:14])=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH:15](=O)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>O(C(O)C)C>[C:1]1([N:7]2[C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=3[N:14]=[C:15]2[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 240BenzaldehydeHCID 68297N-Phenyl-o-phenylenediamine

Product 1

HCID 1376611H-Benzimidazole, 1,2-diphenyl-Yield 37%

Reagents, catalysts & solvents 1

HCID 30156371-MethoxyethanolSolvent

Procedure

N1-phenylbenzene-1,2-diamine (4.15 g, 22 mmol) and benzaldehyde (2.1 g, 20 mmol) were mixed with methoxylethanol (60 ml) in a three-neck flask. The mixture was heated up to reflux for 48 hours. After cooled to room temperature, the solvent was evaporated. The residue was purified by column chromatography using dichloromethane to 5% of ethyl acetate in dichloromethane as eluent. 2 g of desired product was obtained.

Workup

  1. temperatureThe mixture was heated up
  2. temperatureto reflux for 48 hours
  3. customthe solvent was evaporated
  4. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-060636fc728547e29330484f6e5ebe65
Source dataset
uspto-grants-2013_02
Patent number
US08367223B2

Reaction notes

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