Thionyl Chloride → N-(4-chlorobenzyl)-N-(2-chloroethyl)ammonium chloride

HRID 276412Notes

Reaction equation

[Cl:1][C:2]1[CH:12]=[CH:11][C:5]([CH2:6][NH:7][CH2:8][CH2:9]O)=[CH:4][CH:3]=1.O=S(Cl)[Cl:15]>>[Cl-:1].[Cl:1][C:2]1[CH:12]=[CH:11][C:5]([CH2:6][NH2+:7][CH2:8][CH2:9][Cl:15])=[CH:4][CH:3]=1

Participants

Reactant 2

HCID 24386Thionyl Chloride

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

Product 1

HCID 18316438N-(4-chlorobenzyl)-N-(2-chloroethyl)ammonium chloride

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 4-cyano-2-ethylphenyl isothiocyanate to give 2-(4-cyano-2-ethylphenylimino)-3-(4-chlorobenzyl)-1,3-thiazolidine.

Sources & evidence

ORD record: ord-468de80c31c845ff825867ac8d9b3b8e
Source dataset: uspto-grants-2002_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06353006B1

Reaction notes

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