1-(Bromomethyl)-3-chlorobenzene → HCID 18680807, compound

HRID 1699606Notes

Reaction equation

HRID 1699606 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:26]=[CH:27][CH:28]=1)[CH2:5]CCCC(NC1C(CC)=C(C=CC=1[N+]([O-])=O)C([O-])=O)=O.[C:29]([NH:34][C:35]1[C:36](CC)=[C:37]([CH:41]=[CH:42][C:43]=1[N+:44]([O-])=O)[C:38]([O-:40])=[O:39])(=O)[CH2:30][CH2:31][CH3:32].Cl[C:50]1C=C(C=C[CH:57]=1)CBr>>[Cl:1][C:2]1[CH:3]=[C:4]([CH:26]=[CH:27][CH:28]=1)[CH2:5][N:34]1[C:35]2[CH:36]=[C:37]([C:38]([O:40][CH2:50][CH3:57])=[O:39])[CH:41]=[CH:42][C:43]=2[N:44]=[C:29]1[CH2:30][CH2:31][CH3:32]

Participants

4

Reactant 3

HCID 698381-(Bromomethyl)-3-chlorobenzeneHCID 18681016HCID 18681016, compoundHCID 86585384HCID 86585384, compound

Product 1

HCID 18680807HCID 18680807, compound

Procedure

By using the method of example 47, part A, a preliminarily purified material of 3-[N-(3-chlorobenzyl)butyrylamino]-4-nitro-ethylbenzoate isobtained from 3-butyrylamino-4-nitro-ethylbenzoate (1.86 g) and 3-chlorobenzyl bromide (1.64 g). Without purification, this material is changed to 1-(3-chlorobenzyl)-6-ethoxycarbonyl-2-n-propylbenzimidazole (0.57 g) by using the method of example 47, parts B and C. 1H-NMR CDCl3, δ): 1.02 (3H, t, J=7.4 Hz), 1.39 (3H, t, J=7.1 Hz), 1.85-1.92 (2H, m), 2.80 (2H, t, J=7.5 Hz), 4.38 (2H, q, J=7.1 Hz), 5.37 (2H, s), 6.86 (1H, d, J=7.4 Hz), 7.04 (1H, s), 7.21-7.29 (2H, m), 7.77 (1H, d, J=8.4 Hz), 7.96 (1H, d, J=1.2 Hz), 7.99 (1H, dd, J=8.5 and 1.5 Hz).

Workup

  1. customWithout purification

Sources & evidence

ORD record
ord-a0dd13050303438ba5363a9220b1c256
Source dataset
uspto-grants-2002_02
Patent number
US06348032B1

Reaction notes

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