Benzimidazole, 2-butyl- → 4-((2-butyl-1H-benzimidazol-1-yl)-methyl)-benzonitrile

HRID 129852Notes

Reaction equation

HRID 129852 reaction equation
[CH2:1]([C:5]1[NH:9][C:8]2[CH:10]=[CH:11][CH:12]=[CH:13][C:7]=2[N:6]=1)[CH2:2][CH2:3][CH3:4].Br[CH2:15][C:16]1[CH:23]=[CH:22][C:19]([C:20]#[N:21])=[CH:18][CH:17]=1>>[CH2:1]([C:5]1[N:6]([CH2:15][C:16]2[CH:23]=[CH:22][C:19]([C:20]#[N:21])=[CH:18][CH:17]=2)[C:7]2[CH:13]=[CH:12][CH:11]=[CH:10][C:8]=2[N:9]=1)[CH2:2][CH2:3][CH3:4]

Participants

3

Reactant 2

HCID 22122Benzimidazole, 2-butyl-HCID 869964-(Bromomethyl)benzonitrile

Product 1

HCID 149872974-((2-butyl-1H-benzimidazol-1-yl)-methyl)-benzonitrileYield 117%

Procedure

Using the procedure of Step B of Example 1, 3.5 g of 2-butyl-1H-benzimidazol [POOL et al., Am. Soc., Vol. 59, p. 178 (1937)] and 4.3 g of 4-bromomethyl benzonitrile were reacted to obtain 6.8 g of the desired product melting at 130° C. which was dissolved in methylene chloride, treated with activated charcoal, filtered and evaporated to dryness to obtain 6 g of product melting at 130° C. which was crystallized from isopropyl ether to obtain 4.7 g of the expected product melting at 148° C. The analytical sample was obtained by two successive crystallizations of 1.2 g of the product from isopropyl ether to obtain 700 mg of purified product melting at 150° C.

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-b097ecdeb5714fe7ad04008326b95e2a
Source dataset
uspto-grants-1995_11
Patent number
US05470867

Reaction notes

Loading…