Thionyl Chloride → N-cyclopentylmethyl-N-(2-chloroethyl)ammonium chloride

HRID 276383Notes

Reaction equation

[CH:1]1([CH2:6][NH:7][CH2:8][CH2:9]O)[CH2:5][CH2:4][CH2:3][CH2:2]1.O=S(Cl)[Cl:13]>>[Cl-:13].[CH:1]1([CH2:6][NH2+:7][CH2:8][CH2:9][Cl:13])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

Reactant 2

HCID 24386Thionyl Chloride

HCID 18316431N-cyclopentylmethyl-N-(2-hydroxyethyl)amine

Product 1

HCID 18316280N-cyclopentylmethyl-N-(2-chloroethyl)ammonium chloride

Procedure

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

Sources & evidence

ORD record: ord-bca3e032e7ed4133844b9be20bf541ee
Source dataset: uspto-grants-2002_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06353006B1

Reaction notes

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