Réaction #167184

Équation de réaction

diethyl ether hexane

NaH

n-propyl-isothiocyanate

2-chloro-N-phenyl-acetamide

→

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

Solvants

DMF

Conditions de réaction

Traitement

1. 1
   workup.ADDITIONafter completion of the addition
2. 2
   workup.ADDITIONThe mixture is poured onto EA (150 mL)
3. 3
   Extractionis extracted twice with 1 N aq. HCl (200 mL)
4. 4
   workup.ADDITIONby adding 3 N NaOH
5. 5
   Extractionextracted twice with EA (200 mL)
6. 6
   LavageThe organic extracts are washed with water (200 mL)
7. 7
   Autreevaporated
8. 8
   Autreto give a pale yellow, crystalline solid
9. 9
   Filtrationfiltered
10. 10
    Lavagewashed with additional diethyl ether/hexane
11. 11
    Autredried under high vacuum

Mode opératoire

At rt, NaH (154 mg of 55% dispersion in mineral oil, 3.54 mmol) is added in portions to a solution of n-propyl-isothiocyanate (596 mg, 5.90 mmol) and the above 2-chloro-N-phenyl-acetamide (1000 mg, 5.90 mmol) in DMF (30 mL). Stirring is continued for 2 h after completion of the addition. The mixture is poured onto EA (150 mL) and is extracted twice with 1 N aq. HCl (200 mL). The aq. layer is neutralised by adding 3 N NaOH followed by sat. aq. NaHCO3, and extracted twice with EA (200 mL). The organic extracts are washed with water (200 mL) and evaporated to give a pale yellow, crystalline solid. This material is suspended in a small amount of diethyl ether/hexane 1:1, filtered, washed with additional diethyl ether/hexane and dried under high vacuum to give 3-phenyl-2-[(Z)-propylimino]-thiazolidin-4-one.

Source