Dichloromethane → 6-Acetylamino-1-(2-chlorobenzyl)-2-n-propylbenzimidazole

HRID 840772Notes

Reaction equation

HRID 840772 reaction equation
C(O[C:5](=[O:7])[CH3:6])(=O)C.C(Cl)Cl.[NH2:11][C:12]1[CH:13]=[CH:14][C:15]2[N:19]=[C:18]([CH2:20][CH2:21][CH3:22])[N:17]([CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=3[Cl:30])[C:16]=2[CH:31]=1>C(N(CC)CC)C>[C:5]([NH:11][C:12]1[CH:13]=[CH:14][C:15]2[N:19]=[C:18]([CH2:20][CH2:21][CH3:22])[N:17]([CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=3[Cl:30])[C:16]=2[CH:31]=1)(=[O:7])[CH3:6]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 7918Acetic AnhydrideHCID 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 8471TriethylamineSolvent

Procedure

Acetic anhydride (62 mg) is added to a methylene chloride (3 ml) solution of 6-amino-1-(2-chlorobenzyl)-2-n-propylbenzimidazole (150 mg) (example 3) and triethylamine (61 mg) at room temperature, and the solution is stirred for one hour. After it is washed with water and dried, the solvent is removed through evaporation under reduced pressure. The residue is crystallized with ether, and 6-acetylamino-1-(2-chlorobenzyl)-2-n-propylbenzimidazole (143 mg) is obtained. 1H-NMR (CDCl3, δ): 1.00 (3H, t, J=7.5 Hz), 1.86 (2H, m), 2.17 (3H, s), 2.73 (2H, t, J=7.5 Hz), 5.39 (2H, s), 6.43 (1H, d, J=7.5 Hz), 6.98-7.11 (2H, m), 7.22 (1H, t, J=7.5 Hz), 7.45 (1H, d, J=7.5 Hz), 7.59 (1H, brs), 7.68 (1H, d, J=7.5 Hz), 7.84 (1H, d, J=1.5 Hz).

Workup

  1. washAfter it is washed with water
  2. customdried
  3. customthe solvent is removed through evaporation under reduced pressure
  4. customThe residue is crystallized with ether

Sources & evidence

ORD record
ord-8b9240a7c9f74dc78077689f9a5d9af7
Source dataset
uspto-grants-2002_04
Patent number
US06369092B1

Reaction notes

Loading…