Triethylamine → 1-(2-Chlorobenzyl)-6-(4-dimethylaminophenylmethylcarbamoyl)-2-n-propylbenzimidazole

HRID 276007Notes

Reaction equation

HRID 276007 reaction equation
[C:1]([C:4]1[CH:5]=[CH:6][C:7]2[N:11]=[C:10]([CH2:12][CH2:13][CH3:14])[N:9]([CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[Cl:22])[C:8]=2[CH:23]=1)(O)=[O:2].C(Cl)(=O)C(Cl)=O.Cl.[CH3:31][N:32]([CH3:41])[C:33]1[CH:40]=[CH:39][C:36]([CH2:37][NH2:38])=[CH:35][CH:34]=1.C(N(CC)CC)C>C(Cl)Cl.CN(C)C=O>[Cl:22][C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=1[CH2:15][N:9]1[C:8]2[CH:23]=[C:4]([C:1](=[O:2])[NH:38][CH2:37][C:36]3[CH:39]=[CH:40][C:33]([N:32]([CH3:41])[CH3:31])=[CH:34][CH:35]=3)[CH:5]=[CH:6][C:7]=2[N:11]=[C:10]1[CH2:12][CH2:13][CH3:14]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 16211837Benzenemethanamine, 4-(dimethylamino)-, hydrochloride (1:1)HCID 186808696-Carboxy-1-(2-chlorobenzyl)-2-n-propylbenzimidazole

Product 1

HCID 186810821-(2-Chlorobenzyl)-6-(4-dimethylaminophenylmethylcarbamoyl)-2-n-propylbenzimidazoleYield 38.3%

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneCatalystHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

Four-hundred milligrams of 6-carboxy-1-(2-chlorobenzyl)-2-n-propylbenzimidazole were dissolved in 3 ml of methylene chloride containing 1 drop of N,N-dimethylformamide. Oxalyl chloride (28 mg) was added to this solution at 5° C. The thus-obtained solution was stirred at room temperature for 1 hour, and was then concentrated under reduced pressure. The residue was dissolved in 3 ml of methylene chloride, and the mixture was added to a mixed solution prepared by adding 271 mg of 4-dimethylaminobenzylamine hydrochloride and 1 ml of triethylamine to 10 ml of methylene chloride at room temperature. The resulting reaction mixture was stirred at the same temperature for 1 hour, washed with water, dried and then concentrated under reduced pressure. The residue was developed and purified through thin-layer chromatography to give 215 mg of 1-(2-chlorobenzyl)-6-(4-dimethylaminophenylmethylcarbamoyl)-2-n-propylbenzimidazole (61).

Workup

  1. concentrationwas then concentrated under reduced pressure
  2. dissolutionThe residue was dissolved in 3 ml of methylene chloride
  3. additionthe mixture was added to a mixed solution
  4. customprepared
  5. customThe resulting reaction mixture
  6. stirringwas stirred at the same temperature for 1 hour
  7. washwashed with water
  8. customdried
  9. concentrationconcentrated under reduced pressure
  10. custompurified through thin-layer chromatography

Sources & evidence

ORD record
ord-874d255733d342bea25863d0a61a1d75
Source dataset
uspto-grants-2002_03
Patent number
US06352985B1

Reaction notes

Loading…