N-(3,4-dichlorobenzenesulphonyl)-N', S-dimethylisothiourea → N-(3,4-dichlorobenzenesulphonyl)-N'-methyl-N"-[2-((4-methyl-5-imidazolyl)methylthio)ethyl]guanidine

HRID 1974331Notes

Reaction equation

HRID 1974331 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:14]=[C:15]([S:20]([NH:23][C:24](=[N:27][CH3:28])SC)(=[O:22])=[O:21])[CH:16]=[CH:17][C:18]=1[Cl:19]>C(#N)C>[Cl:12][C:13]1[CH:14]=[C:15]([S:20]([NH:23][C:24]([NH:27][CH3:28])=[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:21])=[O:22])[CH:16]=[CH:17][C:18]=1[Cl:19]

Participants

4

Reactant 2

HCID 22756464N-(3,4-dichlorobenzenesulphonyl)-N', S-dimethylisothioureaHCID 178433288HCID 178433288, compound

Product 1

HCID 178485014N-(3,4-dichlorobenzenesulphonyl)-N'-methyl-N"-[2-((4-methyl-5-imidazolyl)methylthio)ethyl]guanidine

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 4-methyl-5-((2-aminoethyl)thiomethyl)imidazole (3.49 g.) and N-(3.4-dichlorobenzenesulphonyl)-N' ,S-dimethylisothiourea (6.20 g.) in acetonitrile (250 ml.) was heated under reflux for 48 hours. Concentration, followed by chromatographic purification on a column of alumina with sequential elution by benzene-ethylacetate (1:4) and benzene-ethanol (1:4) afforded N-(3,4-dichlorobenzenesulphonyl)-N'-methyl-N"-[2-((4-methyl-5-imidazolyl)methylthio)ethyl]guanidine as a glass (1.7 g.)

Workup

  1. temperatureunder reflux for 48 hours
  2. concentrationConcentration
  3. customfollowed by chromatographic purification on a column of alumina with sequential elution by benzene-ethylacetate (1:4) and benzene-ethanol (1:4)

Sources & evidence

ORD record
ord-80d5077872b04fdebaf5c377f084e76c
Source dataset
uspto-grants-1976_12
Patent number
US04000296

Reaction notes

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