Reacción #1553369

Ecuación de reacción

isopropylamine

phenylisothiocyanate

pyridine

methyl bromoacetate

HCl

→

3-phenyl-2-[(Z)-isopropylimino]-thiazolidin-4-one

Disolventes

methanol

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaThe solution which becomes slightly warm during the addition
2. 2
   workup.ADDITIONis added
3. 3
   Extracciónextracted with diethyl ether (150 mL)
4. 4
   workup.ADDITIONby adding sat. aq. NaHCO3
5. 5
   Extracciónextracted with diethyl ether (4×150 mL)
6. 6
   SecadoThe organic extracts are dried over MgSO4
7. 7
   Otroevaporated
8. 8
   Filtraciónfiltered off
9. 9
   Lavadowashed with additional diethyl ether/heptane
10. 10
    Otrodried

Procedimiento

To a solution of isopropylamine (1.31 g, 22.19 mmol) in methanol (25 mL) is added portionwise phenylisothiocyanate (3.0 g, 22.19 mmol). The solution which becomes slightly warm during the addition is stirred at rt for 4 h before pyridine (2.63 g, 33.29 mmol) and methyl bromoacetate (3.39 g, 22.19 mmol) is added. The mixture is stirred for another 16 h at rt before it is poured onto 1 N aq. HCl (100 mL) and extracted with diethyl ether (150 mL). The aq. layer is neutralised by adding sat. aq. NaHCO3 and extracted with diethyl ether (4×150 mL). The organic extracts are dried over MgSO4 and evaporated. The remaining solid is suspended in diethyl ether/heptane, filtered off, washed with additional diethyl ether/heptane and dried to give 3-phenyl-2-[(Z)-isopropylimino]-thiazolidin-4-one.

Fuente