HCID 178433288, compound → HCID 178433320, compound

HRID 616168Notes

Reaction equation

HRID 616168 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].[C:12]1([S:18]([NH:21][C:22](=[NH:25])SC)(=[O:20])=[O:19])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>C(#N)C>[C:12]1([S:18]([NH:21][C:22]([NH:11][CH2:10][CH2:9][S:8][CH2:7][C:6]2[NH:5][CH:4]=[N:3][C:2]=2[CH3:1])=[NH:25])(=[O:19])=[O:20])[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

4

Reactant 2

HCID 178433288HCID 178433288, compoundHCID 178504065HCID 178504065, compound

Product 1

HCID 178433320HCID 178433320, compoundYield 20.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 4-methyl-5-((2-aminoethyl)thiomethyl)imidazole (5.93g.) and N-benzenesulphonyl-S-methylisothiourea (8.0g.) in acetonitrile (100 ml.) was heated under reflux for 24 hours. Concentration, followed by chromatographic purification on a column of silica gel with benzene - methanol (10:1) and recrystallisation from aqueous ethanol and then acetonitrile afforded N-benzenesulphonyl-N'-[2-((4-methyl-5-imidazolyl)methylthio)ethyl]guanidine (2.5 g.) m.p. 149°-150°.

Workup

  1. temperatureunder reflux for 24 hours
  2. concentrationConcentration
  3. customfollowed by chromatographic purification on a column of silica gel with benzene - methanol (10:1) and recrystallisation from aqueous ethanol

Sources & evidence

ORD record
ord-63a328b8e5a64700be14dbfd56fa4c1a
Source dataset
uspto-grants-1978_02
Patent number
US04072748

Reaction notes

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