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

HRID 276333Notes

Reaction equation

[CH:1]1([NH:8][CH2:9][CH2:10]O)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.O=S(Cl)[Cl:14]>>[Cl-:14].[CH:1]1([NH2+:8][CH2:9][CH2:10][Cl:14])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

Reactant 2

HCID 24386Thionyl Chloride

HCID 122178912-Cycloheptylamino-ethanol

Product 1

HCID 18316492N-cycloheptyl-N-(2-chloroethyl)ammonium chloride

Procedure

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

Sources & evidence

ORD record: ord-d7bdb10c8cb94138875bccd63a05d157
Source dataset: uspto-grants-2002_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06353006B1

Reaction notes

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