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

HRID 276342Notes

Reaction equation

[CH:1]1([NH:9][CH2:10][CH2:11]O)[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.O=S(Cl)[Cl:15]>>[Cl-:15].[CH:1]1([NH2+:9][CH2:10][CH2:11][Cl:15])[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

Reactant 2

HCID 24386Thionyl Chloride

HCID 132882152-(Cyclooctylamino)ethan-1-ol

Product 1

HCID 18316362N-cyclooctyl-N-(2-chloroethyl)ammonium chloride

Procedure

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

Sources & evidence

ORD record: ord-11a8c1dc436e4626ba6ef1b098e03354
Source dataset: uspto-grants-2002_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06353006B1

Reaction notes

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