Benzylethanolamine → N-(2-Chloroethyl)benzylamine hydrochloride

Reaction equation

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

Participants

Reactant 2

HCID 4348Benzylethanolamine

HCID 24386Thionyl Chloride

Product 1

HCID 22712N-(2-Chloroethyl)benzylamine hydrochloride

Procedure

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

Sources & evidence

ORD record: ord-15512d3eda824bbe9f9ce97a33317ae9
Source dataset: uspto-grants-2002_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06353006B1

Reaction notes

Loading…