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ChemicalBook CAS DataBase List 3-BENZYL-2-MERCAPTO-3,5-DIHYDRO-4H-IMIDAZOL-4-ONE

3-BENZYL-2-MERCAPTO-3,5-DIHYDRO-4H-IMIDAZOL-4-ONE synthesis

6synthesis methods
-

Yield:39123-65-4 92%

Reaction Conditions:

with pyridine;sodium hydroxide in water at 55; pH=9; for 1 h;

Steps:

2.1. Synthesis of 3-substituted 2-thioxotetrahydro-4H-imidazol-4-ones (1) from glycine and isothiocyanate (typical procedure)

General procedure: Glycine (1 eq.) was dissolved in a 1:1 water-pyridine mixture.Then a 2 M sodium hydroxide solution was added to pH 9, and thispH was maintained until the reaction was completed. The reactionmixture was warmed to 55 °C. At this temperature, isothiocyanate (1.1 eq.) was added. The reaction mixture was stirred at 55 °C for 1h, pH being monitored from time to time. Pyridine and excess ofisothiocyanate were removed by extraction with the same volumeof toluene. Concentrated hydrochloric acid was added to the aqueousphase to pH = 6-7 and the resulting solution was boiled 2.5 h.The reaction mixture was evaporated to half volume underreduced pressure and cooled to room temperature. The formedprecipitate was filtered off and recrystallized from methanol.

References:

Beloglazkina, Elena K.;Krasnovskaya, Olga O.;Guk, Dmitry A.;Tafeenko, Viktor A.;Moiseeva, Anna A.;Zyk, Nikolai V.;Majouga, Alexander G. [Polyhedron,2018,vol. 148,p. 129 - 137]