Benzenemethanamine, 3,4-dichloro- → HCID 3291239, compound

HRID 1176666Notes

Reaction equation

Cl[C:2]1[NH:3][C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=1.[Cl:11][C:12]1[CH:19]=[CH:18][C:15]([CH2:16]Cl)=[CH:14][CH:13]=1.[Cl:20][C:21]1[CH:22]=[C:23]([CH:26]=[CH:27][C:28]=1[Cl:29])[CH2:24][NH2:25]>>[Cl:11][C:12]1[CH:19]=[CH:18][C:15]([CH2:16][N:6]2[C:5]3[CH:7]=[CH:8][CH:9]=[CH:10][C:4]=3[N:3]=[C:2]2[NH:25][CH2:24][C:23]2[CH:26]=[CH:27][C:28]([Cl:29])=[C:21]([Cl:20])[CH:22]=2)=[CH:14][CH:13]=1

Participants

Reactant 3

HCID 1608Benzenemethanamine, 3,4-dichloro-

HCID 77231-Chloro-4-(chloromethyl)benzene

HCID 785722-Chlorobenzimidazole

Product 1

HCID 3291239HCID 3291239, compound

Procedure

The title compound was prepared by Procedure C in two steps from 2-aminobenzimidazole, 4-chlorobenzyl chloride and, subsequently, 3,4-dichlorobenzaldehyde. The product was isolated by preparative LCMS to give the title compound as the free base (yellowish oil). Alternatively, the title compound can be prepared in two steps from 2-chlorobenzimidazole, 4-chlorobenzyl chloride and 3,4-dichlorobenzylamine by use of either Procedure B or by Procedure D. MS(ES+) m/z 416 (M+, 100). 1NMR (CDCl3) δ 4.70 (s, 2H), 5.23 (s, 2H), 7.08-7.33 (m, 11H), 7.46-7.50 (m, 1H).

Sources & evidence

ORD record: ord-28c1c11ecbfe47bf926406c180bfacc7
Source dataset: uspto-grants-2010_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07842817B2

Reaction notes

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