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

HRID 1276871
Notes
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Reaction equation

HRID 1276871 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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

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-f72137fc1611474db50d74ccc2f1060a
Source dataset
uspto-grants-2000_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06166219

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes