N-(4-chlorobenzenesulphonyl)-N',S-dimethylisothiourea → HCID 178485013, compound

HRID 65943Notes

Reaction equation

HRID 65943 reaction equation
[CH3:1][C:2]1[N:3]=[CH:4][NH:5][C:6]=1[CH2:7][S:8][CH2:9][CH2:10][NH2:11].[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([S:19]([NH:22][C:23](=[N:26][CH3:27])SC)(=[O:21])=[O:20])=[CH:15][CH:14]=1>C(#N)C>[Cl:12][C:13]1[CH:14]=[CH:15][C:16]([S:19]([NH:22][C:23]([NH:26][CH3:27])=[N:11][CH2:10][CH2:9][S:8][CH2:7][C:6]2[NH:5][CH:4]=[N:3][C:2]=2[CH3:1])(=[O:20])=[O:21])=[CH:17][CH:18]=1

Participants

4

Reactant 2

HCID 22756462N-(4-chlorobenzenesulphonyl)-N',S-dimethylisothioureaHCID 178433288HCID 178433288, compound

Product 1

HCID 178485013HCID 178485013, compoundYield 59.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 4-methyl-5-((2-aminoethyl)thiomethyl)imidazole (3.33 g.) and N-(4-chlorobenzenesulphonyl)-N',S-dimethylisothiourea (5.40 g.) in acetonitrile was heated under reflux for 24 hours. Concentration, followed by recrystallisation from aqueous ethanol afforded N-(4-chlorobenzenesulphonyl)-N'-methyl-N"-[2-((4-methyl-5-imidazolyl)-methylthio)ethyl]guanidine (4.6 g.), m.p. 153°-154°.

Workup

  1. temperatureunder reflux for 24 hours
  2. concentrationConcentration
  3. customfollowed by recrystallisation from aqueous ethanol

Sources & evidence

ORD record
ord-6dcf18a03c1649e69e8e4badb8f4e142
Source dataset
uspto-grants-1978_12
Patent number
US04129657

Reaction notes

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