Diethyl Ether → 2-(4-Fluorophenyl)-1-phenyl-1H-benzimidazole

HRID 586760Notes

Reaction equation

HRID 586760 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.[F:22][C:23]1[CH:31]=[CH:30][C:26]([C:27](Cl)=O)=[CH:25][CH:24]=1.CCOCC>ClCCl>[F:22][C:23]1[CH:31]=[CH:30][C:26]([C:27]2[N:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=3[N:14]=2)=[CH:25][CH:24]=1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 8471TriethylamineHCID 678794-Fluorobenzoyl chlorideHCID 68297N-Phenyl-o-phenylenediamine

Product 1

HCID 208261702-(4-Fluorophenyl)-1-phenyl-1H-benzimidazoleYield 80%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

N-phenyl-1,2-phenylenediamine (1.84 g, 10 mmol) and 30 ml of dichloromethane were charged in a 250 ml round bottle, 3 ml of triethylamine was then added, and the mixture was cooled to 0° C. 4-Fluoro-benzoyl chloride (1.58 g, 10 mmol) was dissolved in 30 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 2-(4-fluoro-phenyl)-1-phenyl-1H-benzoimidazole (yield=2.3 g, 80%).

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-b4f51e8637674c4882d438a693e64fbf
Source dataset
uspto-grants-2005_08
Patent number
US06936716B1

Reaction notes

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