4-Chlorobenzaldehyde → N-(4-Chlorobenzyl)-3H-benzo[d]imidazol-5-amine

HRID 45928

Reaction equation

HRID 45928 reaction equation
[N:1]1[C:5]2[CH:6]=[CH:7][C:8]([NH2:10])=[CH:9][C:4]=2[NH:3][CH:2]=1.[Cl:11][C:12]1[CH:19]=[CH:18][C:15]([CH:16]=O)=[CH:14][CH:13]=1.[BH4-].[Na+].[OH-].[Na+]>>[Cl:11][C:12]1[CH:19]=[CH:18][C:15]([CH2:16][NH:10][C:8]2[CH:7]=[CH:6][C:5]3[N:1]=[CH:2][NH:3][C:4]=3[CH:9]=2)=[CH:14][CH:13]=1

Participants

5

Reactant 4

HCID 77264-ChlorobenzaldehydeHCID 136235-AminobenzimidazoleHCID 14798Sodium HydroxideHCID 4311764Sodium borohydride

Product 1

HCID 67444221N-(4-Chlorobenzyl)-3H-benzo[d]imidazol-5-amine

Procedure

Alternatively the compound was synthesized starting from benzimidazol-5-amine (2.66 g; 20 mmol; 1 eq.), 4-chlorobenzaldehyde (3.09 g; 22 mmol; 1.1 eq.), NaBH4 (1.14 g; 30 mmol; 1.5 eq.) and 5 N NaOH (20 ml; 100 mmol; 5 eq.) according to method 2; Yield: 3.94 g (76.7%); MS m/z: 258.3/260.3 [M+H]+

Workup

  1. customAlternatively the compound was synthesized

Sources & evidence

ORD record
ord-cefdeab8e05a489a85e32512c71a144a
Source dataset
uspto-grants-2013_09
Patent number
US08541596B2

Linked notes

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