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

HRID 840771Notes

Reaction equation

HRID 840771 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

6-t-Butoxycarbonylamino-1-(2-chlorobenzyl)-2-n-propylbenzimidazole (700 mg) (example 1) is dissolved in a mixture solvent of methylene chloride (10 ml) and trifluoroacetic acid (1 ml), and the solution is stirred for five hours at room temperature. A small amount of methylene chloride is added into the reaction solution, and the solution is washed with sodium carbonate aqueous solution. After it is dried, the solvent is removed through evaporation. The residue is crystallized using a mixture solvent of normal hexane and ether, and 6-amino-1-(2-chlorobenzyl)-2-n-propylbenzimidazole (455 mg) is obtained. 1H-NMR (CDCl3, δ): 1.01 (3H, t, J=7.5 Hz), 1.86 (2H, m), 2.73 (2H, t, J=7.5 Hz), 5.30 (2H, s), 6.41 (1H, d, J=1.5 Hz), 6.48 (1H, d, J=7.5 Hz), 6.66 (1H, dd, J=7.5 and 1.5 Hz), 7.10 (1H, t, J=7.5 Hz), 7.25 (1H, t, J=7.5 Hz), 7.46 (1H, d, J=7.5 Hz), 7.57 (1H, d, J=7.5 Hz).

Workup

  1. washthe solution is washed with sodium carbonate aqueous solution
  2. customAfter it is dried
  3. customthe solvent is removed through evaporation
  4. customThe residue is crystallized

Sources & evidence

ORD record
ord-c3a16f087f7b4b09b7e36ea446f58e7c
Source dataset
uspto-grants-2002_04
Patent number
US06369092B1

Reaction notes

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