5-Nitrobenzimidazole → HCID 18379835, compound

HRID 2186087Notes

Reaction equation

HRID 2186087 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][C:7]2[N:8]=[CH:9][NH:10][C:6]=2[CH:5]=1)([O-])=O.[CH3:13][O:14][C:15]1[CH:22]=[CH:21][C:18]([CH2:19]Cl)=[CH:17][CH:16]=1>[H][H].[Pd].CC(O)C.C(Cl)Cl>[CH3:13][O:14][C:15]1[CH:22]=[CH:21][C:18]([CH2:19][N:8]2[C:7]3[CH:11]=[CH:12][C:4]([NH2:1])=[CH:5][C:6]=3[N:10]=[CH:9]2)=[CH:17][CH:16]=1.[CH3:13][O:14][C:15]1[CH:22]=[CH:21][C:18]([CH2:19][N:10]2[C:6]3[CH:5]=[C:4]([NH2:1])[CH:12]=[CH:11][C:7]=3[N:8]=[CH:9]2)=[CH:17][CH:16]=1

Participants

6

Reactant 2

HCID 71955-NitrobenzimidazoleHCID 699934-Methyloxybenzyl chloride

Product 2

HCID 16244170HCID 16244170, compoundYield 43%HCID 18379835HCID 18379835, compoundYield 48%

Reagents, catalysts & solvents 2

HCID 178506449HCID 178506449, compoundCatalystHCID 21966342Isopropanol methylene chlorideSolvent

Procedure

A reaction of 5-nitrobenzimidazole (4.3 g, 27 mmol) and 4-methoxybenzyl chloride (4.3 ml, 30 mmol) in a procedure described in Example 9 produces 5.6 g .(19 mmol, 73%) of a mixture of 1- and 3-(4-methoxybenzyl) -5-nitrobenzimidazole, which was converted to the corresponding amines in hydrogenation (H2/Pd-C). The amine mixture was subjected to column chromatography (10%-30% i-PrOH/CH2Cl2) to provide 2.1 g (8.2 mmol, 43%) of 1-(4-methoxybenzyl)-5-aminobenzimidazole and 2.4 g (9.2 mmol, 48%) of 3-(4-methoxybenzyl)-5-aminobenzimidazole.

Workup

  1. customproduces 5.6 g

Sources & evidence

ORD record
ord-9aee6d9fdb0f45a2a5d635212dba4512
Source dataset
uspto-grants-2002_06
Patent number
US06403626B1

Reaction notes

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