Benzoyl chloride → 7-Benzoylamino-1-phenyl-5-trifluoromethylbenzimidazole

HRID 644502Notes

Reaction equation

HRID 644502 reaction equation
[NH2:1][C:2]1[C:7]2[N:8]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[CH:9]=[N:10][C:6]=2[CH:5]=[C:4]([C:17]([F:20])([F:19])[F:18])[CH:3]=1.[C:21](Cl)(=[O:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C(N(CC)CC)C>O1CCCC1>[C:21]([NH:1][C:2]1[C:7]2[N:8]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[CH:9]=[N:10][C:6]=2[CH:5]=[C:4]([C:17]([F:20])([F:19])[F:18])[CH:3]=1)(=[O:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 113003637-Amino-1-phenyl-5-trifluoromethylbenzimidazole

Product 1

HCID 114176547-Benzoylamino-1-phenyl-5-trifluoromethylbenzimidazoleYield 38%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 7-amino-1-phenyl-5-trifluoromethylbenzimidazole (300 mg, 1 mmol), benzoylchloride (0.23 ml, 2 mmol) and triethyl amine (0.3 ml, 2 mmol) in tetrahydrofurane (10 ml) was stirred at ambient temperature overnight. The solvent was removed under reduced pressure and the residue was partitioned between ethyl acetate and hydro chloric acid (4M). The aqueous phase was rendered alkaline with saturated, aqueous sodium carbonate and extracted with ethyl acetate. The extract was dried and concentrated under reduced pressure and the resultant gum was triturated with a mixture of diethyl ether and petroleum ether to leave the solid, off-white product (145 mg, 38%), m/z, 382.1 (M+H)+.

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe residue was partitioned between ethyl acetate and hydro chloric acid (4M)
  3. extractionextracted with ethyl acetate
  4. customThe extract was dried
  5. concentrationconcentrated under reduced pressure
  6. customthe resultant gum was triturated with a mixture of diethyl ether and petroleum ether

Sources & evidence

ORD record
ord-226f1780edcc49fd864316e406b85706
Source dataset
uspto-grants-2010_04
Patent number
US07700638B2

Reaction notes

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