4-Sulfanylidene-1,3-thiazolidin-2-one → 4-[2-[(5-methyl-1H-imidazol-4-yl)methylsulfanyl]ethylamino]-5H-1,3-thiazol-2-one

HRID 434631Notes

Reaction equation

HRID 434631 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].[S:12]1[CH2:16][C:15](=S)[NH:14][C:13]1=[O:18]>CO>[CH3:1][C:2]1[N:3]=[CH:4][NH:5][C:6]=1[CH2:7][S:8][CH2:9][CH2:10][NH:11][C:15]1[CH2:16][S:12][C:13](=[O:18])[N:14]=1

Participants

4

Reactant 2

HCID 15395954-Sulfanylidene-1,3-thiazolidin-2-oneHCID 178433288HCID 178433288, compound

Product 1

HCID 1784332944-[2-[(5-methyl-1H-imidazol-4-yl)methylsulfanyl]ethylamino]-5H-1,3-thiazol-2-oneYield 37%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 4-methyl-5-[(2-aminoethyl)thiomethyl]imidazole (1.71 g.) and thiazolidine-2-one-4-thione (1.33 g.) in methanol (30 ml.) was heated under reflux for one hour. Concentration, followed by successive recrystallisation of the residue from methanol, ethanol and aqueous ethanol afforded 4-[2-((4-methyl-5-imidazolyl)methylthio)ethylamino]thiazoline-2-one (1.0 g.) m.p. 195°-197°.

Workup

  1. temperatureunder reflux for one hour
  2. concentrationConcentration
  3. customfollowed by successive recrystallisation of the residue from methanol, ethanol and aqueous ethanol

Sources & evidence

ORD record
ord-5f418ae52c2a49ac9857e10d9de0bce7
Source dataset
uspto-grants-1983_08
Patent number
US04399142

Reaction notes

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