HCID 9952790, compound → 1-(2-Chlorobenzyl)-2-propyl-1H-benzo[d]imidazol-6-amine

HRID 276012Notes

Reaction equation

HRID 276012 reaction equation
C(OC([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)(C)(C)C>C(Cl)Cl.FC(F)(F)C(O)=O>[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

Participants

4

Reactant 1

HCID 9952790HCID 9952790, compound

Product 1

HCID 120423481-(2-Chlorobenzyl)-2-propyl-1H-benzo[d]imidazol-6-amineYield 86.7%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 6422Trifluoroacetic acidSolvent

Procedure

Seven-hundred milligrams of 6-tert-butoxycarbonylamino-1-(2-chlorobenzyl)-2-n-propylbenzimidazole were dissolved in a mixed solvent of 10 ml of methylene chloride and 1 ml of trifluoroacetic acid, and the mixture was stirred at room temperature for 5 hours. A small amount of methylene chloride was added to the reaction solution. The mixture was washed with a sodium carbonate aqueous solution, and was dried. The solvent was then distilled off. The residue was crystallized from a mixed solvent of n-hexane and ether to give 455 mg of 6-amino-1-(2-chlorobenzyl)-2-n-propylbenzimidazole (90).

Workup

  1. washThe mixture was washed with a sodium carbonate aqueous solution
  2. customwas dried
  3. distillationThe solvent was then distilled off
  4. customThe residue was crystallized from a mixed solvent of n-hexane and ether

Sources & evidence

ORD record
ord-2fc84ebb48c340548126ef2321addbed
Source dataset
uspto-grants-2002_03
Patent number
US06352985B1

Reaction notes

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