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

HRID 276392Notes

Reaction equation

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

Participants

Reactant 2

HCID 24386Thionyl Chloride

HCID 132882132-[(Cyclohexylmethyl)amino]ethan-1-ol

Product 1

HCID 18316318N-cyclohexylmethyl-N-(2-chloroethyl)ammonium chloride

Procedure

2-Hydroxyethylamine was reacted with cyclohexylmethyl bromide according to Method B2a to give N-cyclohexylmethyl-N-(2-hydroxyethyl)amine. The alcohol was reacted with SOCl2 according to Method B7c to give N-cyclohexylmethyl-N-(2-chloroethyl)ammonium chloride. The chloroethylamine was reacted with 2-methoxy4-nitrophenyl isothiocyanate to give 2-(2-methoxy-4-nitrophenylimino)-3-(cyclohexylmethyl)-1,3-thiazolidine.

Sources & evidence

ORD record: ord-22f796017255461d9562aa39e8069e5b
Source dataset: uspto-grants-2002_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06353006B1

Reaction notes

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