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

HRID 276350Notes

Reaction equation

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

Participants

Reactant 2

HCID 24386Thionyl Chloride

HCID 183161002-[(Cyclopropylmethyl)amino]ethan-1-ol

Product 1

HCID 18316126N-cyclopropylmethyl-N-(2-chloroethyl)ammonium chloride

Procedure

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

Sources & evidence

ORD record: ord-52c495cb49b64b7fa86a18dae363d807
Source dataset: uspto-grants-2002_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06353006B1

Reaction notes

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