3-Chloro-4-isothiocyanato-benzonitrile → 2-(2-Chloro-4-cyanophenylimino)-3-(4-chlorobenzyl)-1,3-thiazolidine

HRID 276416Notes

Reaction equation

HRID 276416 reaction equation
[Cl-].[Cl:2][C:3]1[CH:13]=[CH:12][C:6]([CH2:7][NH2+:8][CH2:9][CH2:10]Cl)=[CH:5][CH:4]=1.[Cl:14][C:15]1[CH:20]=[C:19]([C:21]#[N:22])[CH:18]=[CH:17][C:16]=1[N:23]=[C:24]=[S:25]>>[Cl:14][C:15]1[CH:20]=[C:19]([C:21]#[N:22])[CH:18]=[CH:17][C:16]=1[N:23]=[C:24]1[N:8]([CH2:7][C:6]2[CH:12]=[CH:13][C:3]([Cl:2])=[CH:4][CH:5]=2)[CH2:9][CH2:10][S:25]1

Participants

3

Reactant 2

HCID 183163923-Chloro-4-isothiocyanato-benzonitrileHCID 18316438N-(4-chlorobenzyl)-N-(2-chloroethyl)ammonium chloride

Product 1

HCID 183163982-(2-Chloro-4-cyanophenylimino)-3-(4-chlorobenzyl)-1,3-thiazolidine

Procedure

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

Sources & evidence

ORD record
ord-700d514caaba4a5499af04413edbb529
Source dataset
uspto-grants-2002_03
Patent number
US06353006B1

Reaction notes

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