Reaktion #305029

Reaktionsgleichung

4-(methylsulfonyl)phenylhydrazine hydrochloride

4,4-dimethyl-3-oxopentanenitrile

HCl

→

3-tert-butyl-1-(4-(methylsulfonyl)phenyl)-1H-pyrazol-5-amine

Lösungsmittel

NaOH

EtOAc

EtOH

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturthe suspension was heated
2. 2
   Temperaturto reflux for 27 h, during which time all solids
3. 3
   workup.DISSOLUTIONgradually dissolved
4. 4
   Sonstigeto give a yellow solution
5. 5
   workup.ADDITIONwas added
6. 6
   SonstigeThe organic layer was isolated
7. 7
   Trocknendried (MgSO4)
8. 8
   Filtrationfiltered
9. 9
   Einengenconcentrated
10. 10
    Sonstigeto give a yellow crystalline solid

Vorschrift

4-(methylsulfonyl)phenylhydrazine hydrochloride (1.133 g, 5.09 mmol) and 4,4-dimethyl-3-oxopentanenitrile (0.697 g, 5.57 mmol) were weighed into a 100 mL RBF. 0.2 M HCl in EtOH (42 mL) was added and the suspension was heated to reflux for 27 h, during which time all solids gradually dissolved to give a yellow solution. The solution was diluted with 1 M NaOH(aq) (˜16 mL) to pH 12-13, EtOAc (70 mL) was added and the biphasic system was vigorously stirred for 5 min. The organic layer was isolated, dried (MgSO4), filtered and concentrated to give a yellow crystalline solid. Yield: 1.42 g (95%).

Quelle