1-Chloro-3-isothiocyanato-2-methylbenzene → 2-(3-Chloro-2-methylphenylimino)-3-(cyclobutylmethyl)-1,3-thiazolidine

HRID 276366

Reaction equation

HRID 276366 reaction equation
[Cl-].[CH:2]1([CH2:6][NH2+:7][CH2:8][CH2:9]Cl)[CH2:5][CH2:4][CH2:3]1.[Cl:11][C:12]1[C:13]([CH3:21])=[C:14]([N:18]=[C:19]=[S:20])[CH:15]=[CH:16][CH:17]=1>>[Cl:11][C:12]1[C:13]([CH3:21])=[C:14]([N:18]=[C:19]2[N:7]([CH2:6][CH:2]3[CH2:3][CH2:4][CH2:5]3)[CH2:8][CH2:9][S:20]2)[CH:15]=[CH:16][CH:17]=1

Participants

3

Reactant 2

HCID 1405041-Chloro-3-isothiocyanato-2-methylbenzeneHCID 18316353N-cyclobutylmethyl-N-(2-chloroethyl)ammonium chloride

Product 1

HCID 183162322-(3-Chloro-2-methylphenylimino)-3-(cyclobutylmethyl)-1,3-thiazolidine

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-chloro-2-methylphenyl isothiocyanate to give 2-(3-chloro-2-methylphenylimino)-3-(cyclobutylmethyl)-1,3-thiazolidine.

Sources & evidence

ORD record
ord-5983525318024b46868aa9d474489f11
Source dataset
uspto-grants-2002_03
Patent number
US06353006B1

Linked notes

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