Réaction #1596941

Équation de réaction

N-(1-hydroxy-2-methylpropan-2-yl)-N′-phenylthiourea

NaOH

→

title compound

Rendement 30.2%

4,4-dimethyl-N-phenyl-4,5-dihydrothiazol-2-amine

Rendement 30.2%

Solvants

HCl

Conditions de réaction

Traitement

1. 1
   TempératureAfter cooling
2. 2
   Extractionextracted with diethyl ether
3. 3
   LavageThe extract was washed with saturated brine
4. 4
   workup.ADDITIONanhydrous sodium sulfate was added
5. 5
   workup.DISTILLATIONThe organic phase was distilled off under reduced pressure
6. 6
   Lavagethe residue was washed three times with hexane
7. 7
   AutreThe crystals thus obtained
8. 8
   Autrewere dried under reduced pressure at room temperature
9. 9
   Autrerecrystallized from methanol twice

Mode opératoire

N-(1-hydroxy-2-methylpropan-2-yl)-N′-phenylthiourea (80.1 g, 0.36 mol) was dissolved in 2,400 mL of 35% HCl, and the resulting mixture was stirred while heating at 90° C. for 1.5 hours. After cooling, the mixture was neutralized with NaOH and extracted with diethyl ether. The extract was washed with saturated brine and then anhydrous sodium sulfate was added. The organic phase was distilled off under reduced pressure and the residue was washed three times with hexane. The crystals thus obtained were dried under reduced pressure at room temperature, and then recrystallized from methanol twice to give 22.4 g of the title compound (yield 18%).

Source