Chloroacetic Acid → 2-(chloromethyl)-4-methoxy-1H-benzo[d]imidazole

HRID 7089

Reaction equation

HRID 7089 reaction equation
[NH2:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][CH:5]=[CH:4][C:3]=1[N+:10]([O-])=O.[Cl:13][CH2:14][C:15](O)=O.Cl>CO.[Pd]>[Cl:13][CH2:14][C:15]1[NH:10][C:3]2[CH:4]=[CH:5][CH:6]=[C:7]([O:8][CH3:9])[C:2]=2[N:1]=1

Participants

6

Reactant 3

HCID 300Chloroacetic AcidHCID 313Hydrochloric AcidHCID 854916-Nitro-o-anisidine2×

Product 1

HCID 220187532-(chloromethyl)-4-methoxy-1H-benzo[d]imidazoleYield 86.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 2-amino-3-methoxy-1-nitrobenzene (0.860 g, 5.11 mmol) in MeOH (50 mL) was hydrogenated (1 atm) over palladium, 10 wt. % on activated carbon (0.163 g). The resultant crude 3-methoxy-1,2-phenylenediamine was reacted with chloroacetic acid (0.953 g, 10.08 mmol) in refluxing 4 N HCl (10 mL) overnight. After aqueous workup, 0.87 g of 2-chloromethyl-4-methoxy-1H-benzimidazole was isolated as a red-brown solid, which was used without further purification.

Sources & evidence

ORD record
ord-24bc86431bd542409b1544b66fd7149e
Source dataset
uspto-grants-2006_08
Patent number
US07084155B2

Linked notes

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