Thionyl Chloride → 1h-Benzimidazole,6-(chloromethyl)-1-[(2-chlorophenyl)methyl]-2-methyl-,hydrochloride

HRID 840773Notes

Reaction equation

HRID 840773 reaction equation
S(Cl)([Cl:3])=O.[Cl:5][C:6]1[CH:24]=[CH:23][CH:22]=[CH:21][C:7]=1[CH2:8][N:9]1[C:13]2[CH:14]=[C:15]([CH2:18][Cl:19])[CH:16]=[CH:17][C:12]=2[N:11]=[C:10]1[CH3:20]>>[ClH:3].[Cl:5][C:6]1[CH:24]=[CH:23][CH:22]=[CH:21][C:7]=1[CH2:8][N:9]1[C:13]2[CH:14]=[C:15]([CH2:18][Cl:19])[CH:16]=[CH:17][C:12]=2[N:11]=[C:10]1[CH3:20]

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 226203421h-Benzimidazole,6-(chloromethyl)-1-[(2-chlorophenyl)methyl]-2-methyl-

Product 1

HCID 226203411h-Benzimidazole,6-(chloromethyl)-1-[(2-chlorophenyl)methyl]-2-methyl-,hydrochloride

Procedure

Thionyl chloride (5 ml) is added to 1-(2-chlorobenzyl)-6-chloromethyl-2-methylbenzimidazole (3.56 g), and the solution is stirred for 20 minutes at room temperature and then for 20 minutes at 80° C. After excess thionyl chloride is removed through evaporation under reduced pressure, the residue is dissolved in chloroform (10 ml), and crystallization is performed by adding hexane. The crystals are separated through filtration, washed in hexane, and dried. Thus, 1-(2-chlorobenzyl)-6-chloromethyl-2-methylbenzimidazole hydrochloride (4.07 g) is obtained. 1H-NMR (CDCl3, δ): 3.01 (3H, s), 4.68 (2H, s), 5.61 (2H. s), 6.71 (1H, d, J=7.5 Hz), 7.24-7.29 (1H, m), 7.38 (1H, t, J=7.7 Hz), 7.44 (1H, s), 7.52 (2H, d, J=8.2 Hz), 7.92 (1H, d J=8.4 Hz).

Workup

  1. waitfor 20 minutes at 80° C
  2. customAfter excess thionyl chloride is removed through evaporation under reduced pressure
  3. dissolutionthe residue is dissolved in chloroform (10 ml)
  4. customcrystallization
  5. additionby adding hexane
  6. customThe crystals are separated through filtration
  7. washwashed in hexane
  8. customdried

Sources & evidence

ORD record
ord-62c727f2abeb4eb3a39ee878752d630f
Source dataset
uspto-grants-2002_04
Patent number
US06369092B1

Reaction notes

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