Ethanolamine → 2-(4-Chloro-benzylamino)-ethanol

HRID 276414Notes

Reaction equation

[OH:1][CH2:2][CH2:3][NH2:4].[Cl:5][C:6]1[CH:13]=[CH:12][C:9]([CH2:10]Br)=[CH:8][CH:7]=1>>[Cl:5][C:6]1[CH:13]=[CH:12][C:9]([CH2:10][NH:4][CH2:3][CH2:2][OH:1])=[CH:8][CH:7]=1

Participants

Reactant 2

HCID 700Ethanolamine

HCID 693291-(Bromomethyl)-4-chlorobenzene

Product 1

HCID 4244522-(4-Chloro-benzylamino)-ethanol

Procedure

2-Hydroxyethylamine was reacted with 4-chlorobenzyl bromide according to Method B2a to give N-(4-chlorobenzyl)-N-(2-hydroxyethyl)amine. The alcohol was reacted with SOCl2 according to Method B7c to give N-(4-chlorobenzyl)-N-(2-chloroethyl)ammonium chloride. The chloroethylamine was reacted with 2-chloro-4-cyanophenyl isothiocyanate to give 2-(2-chloro-4-cyanophenylimino)-3-(4-chlorobenzyl)-1,3-thiazolidine.

Sources & evidence

ORD record: ord-a9dbb2ab1f184081b7fcc55239881fd1
Source dataset: uspto-grants-2002_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06353006B1

Reaction notes

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