Diethyl Ether → 1H-Benzimidazole, 1,2-diphenyl-

HRID 1818642Notes

Reaction equation

HRID 1818642 reaction equation
[C:1]1([NH:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[NH2:14])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.[C:22](Cl)(=O)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.CCOCC>ClCCl>[C:1]1([N:7]2[C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=3[N:14]=[C:22]2[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 68297N-Phenyl-o-phenylenediamine

Product 1

HCID 1376611H-Benzimidazole, 1,2-diphenyl-Yield 70%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

40 ml of N-phenyl-1,2-phenylenediamine (7.36 g, 40 mmol) was charged in a 250 ml round bottle, 10 ml of triethylamine was then added, and the mixture was cooled to 0° C. Benzoyl chloride (5.6 g, 40 mmol) was dissolved in 40 ml of dichloromethane and then slowly added to the 250 ml round bottle. The reaction was conducted under a nitrogen atmosphere for 6 hours. After the reaction was complete, ether was added to form precipitate. The solid product was collected by filtration, washed with ether several times, and heated under reduced pressure to form 1,2-diphenyl-1H-benzoimidazole (yield=7.56 g, 70%).

Workup

  1. additionwas then added
  2. additionslowly added to the 250 ml round bottle
  3. customto form precipitate
  4. filtrationThe solid product was collected by filtration
  5. washwashed with ether several times
  6. temperatureheated under reduced pressure

Sources & evidence

ORD record
ord-c4a492a6ef0c4eb5a7bd9fc6c6ef60f4
Source dataset
uspto-grants-2009_10
Patent number
US07601437B2

Reaction notes

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