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

HRID 586759Notes

Reaction equation

HRID 586759 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 precipitation. 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
  4. customprecipitation
  5. filtrationThe solid product was collected by filtration
  6. washwashed with ether several times
  7. temperatureheated under reduced pressure

Sources & evidence

ORD record
ord-e2538fe424994bf8b90c40259d35f854
Source dataset
uspto-grants-2005_08
Patent number
US06936716B1

Reaction notes

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