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

HRID 586761Notes

Reaction equation

HRID 586761 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][CH:29]=[CH:28][C:24]=1[C:25](Cl)=O.CCOCC>ClCCl>[F:22][C:23]1[CH:31]=[CH:30][CH:29]=[CH:28][C:24]=1[C:25]1[N:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[N:14]=1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 8471TriethylamineHCID 98082-Fluorobenzoyl chlorideHCID 68297N-Phenyl-o-phenylenediamine

Product 1

HCID 208261682-(2-Fluorophenyl)-1-phenyl-1H-benzimidazoleYield 75%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

N-phenyl-1,2-phenylenediamine (3.68 g, 20 mmol) and 40 ml of dichloromethane were charged in a 250 ml round bottle, 5 ml of triethylamine was then added, and the mixture was cooled to 0° C. 2-Fluoro-benzoyl chloride (3.16 g, 20 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 2-(2-fluoro-phenyl)-1-phenyl-1H-benzoimidazole (yield=4.32 g, 75%).

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-8a9725325dd740bbbf9ae09afa50be34
Source dataset
uspto-grants-2005_08
Patent number
US06936716B1

Reaction notes

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