Chloroacetic Acid → 2-chloromethyl-4-phenyl-1H-benzimidazole

HRID 7091

Reaction equation

HRID 7091 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:3]=1[N+:14]([O-])=O.[Cl:17][CH2:18][C:19](O)=O>CO.[Pd]>[Cl:17][CH2:18][C:19]1[NH:1][C:2]2[CH:7]=[CH:6][CH:5]=[C:4]([C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=3)[C:3]=2[N:14]=1

Participants

5

Reactant 2

HCID 300Chloroacetic AcidHCID 105127972-Amino-6-phenyl-nitrobenzene2×

Product 1

HCID 220186182-chloromethyl-4-phenyl-1H-benzimidazoleYield 92.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 2-amino-6-phenyl-nitrobenzene (0.600 g, 2.80 mmol) in MeOH (28 mL) was hydrogenated (30 psi) over palladium, 10 wt. % on activated carbon (0.121 g). The resultant crude 3-phenyl-1,2-phenylenediamine was reacted with chloroacetic acid (0.537 g, 5.68 mmol) in refluxing 4 N Hl (6 mL) overnight. After normal workup, 0.63 g (92%) of 2-chloromethyl-4-phenyl-1H-benzimidazole was isolated as a brown solid, which was used without further purification.

Workup

  1. temperaturein refluxing 4 N Hl (6 mL) overnight

Sources & evidence

ORD record
ord-ba58e1f0c66642b68d676298060dbc50
Source dataset
uspto-grants-2006_08
Patent number
US07084155B2

Linked notes

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