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

HRID 276359Notes

Reaction equation

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

Participants

Reactant 2

HCID 24386Thionyl Chloride

HCID 183163062-((Cyclobutylmethyl)amino)ethanol

Product 1

HCID 18316353N-cyclobutylmethyl-N-(2-chloroethyl)ammonium chloride

Procedure

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

Sources & evidence

ORD record: ord-64e8394378e3467ab90beae665901181
Source dataset: uspto-grants-2002_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06353006B1

Reaction notes

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