Acetic Anhydride → 6-Acetylamino-1-(2-chlorobenzyl)-2-n-propylbenzimidazole

HRID 276011Notes

Reaction equation

HRID 276011 reaction equation
C(O[C:5](=[O:7])[CH3:6])(=O)C.[NH2:8][C:9]1[CH:10]=[CH:11][C:12]2[N:16]=[C:15]([CH2:17][CH2:18][CH3:19])[N:14]([CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[Cl:27])[C:13]=2[CH:28]=1.C(N(CC)CC)C>C(Cl)Cl>[C:5]([NH:8][C:9]1[CH:10]=[CH:11][C:12]2[N:16]=[C:15]([CH2:17][CH2:18][CH3:19])[N:14]([CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[Cl:27])[C:13]=2[CH:28]=1)(=[O:7])[CH3:6]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 120423481-(2-Chlorobenzyl)-2-propyl-1H-benzo[d]imidazol-6-amine

Product 1

HCID 226203346-Acetylamino-1-(2-chlorobenzyl)-2-n-propylbenzimidazoleYield 83.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Acetic anhydride (62 mg) was added to a solution of 150 mg of 6-amino-1-(2-chlorobenzyl)-2-n-propylbenzimidazole and 61 mg of triethylamine in 3 ml of methylene chloride at room temperature, and the mixture was stirred for 1 hour. The reaction mixture was washed with water, and was then dried. The solvent was distilled off under reduced pressure. The residue was crystallized with ether to give 143 mg of 6-acetylamino-1-(2-chlorobenzyl)-2-n-propylbenzimidazole (89).

Workup

  1. washThe reaction mixture was washed with water
  2. customwas then dried
  3. distillationThe solvent was distilled off under reduced pressure
  4. customThe residue was crystallized with ether

Sources & evidence

ORD record
ord-9460f47d03324717ab734aaa7167f101
Source dataset
uspto-grants-2002_03
Patent number
US06352985B1

Reaction notes

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