Reaktion #73498

Reaktionsgleichung

methyl 2-acetyl-3-methyl-3-phenylbutanoate

N-ethyl-6-hydrazino-N-phenylpyridine-3-sulfonamide

→

N-ethyl-6-[3-methyl-4-(1-methyl-1-phenylethyl)-5-oxo-2,5-dihydro-1H-pyrazol-1-yl]-N-phenylpyridine-3-sulfonamide

Ausbeute 44.0%

Lösungsmittel

pentane

EtOH AcOH

Reaktionsbedingungen

Aufarbeitung

1. 1
   EinengenAfter concentrating under reduced pressure
2. 2
   Waschenwashed with 2×30 mL of saturated NaHCO3 solution
3. 3
   Trocknendried over Na2SO4
4. 4
   Filtrationfiltered
5. 5
   Einengenconcentrated under reduced pressure
6. 6
   Sonstigepurified by chromatography on a column of silica gel
7. 7
   Wascheneluting with a cyclohexane/EtOAc gradient of 0 to 20% EtOAc
8. 8
   EinengenAfter concentrating under reduced pressure, 312 mg of a yellow oil
9. 9
   Sonstigeare obtained
10. 10
    SonstigeThe solid obtained
11. 11
    Filtrationis filtered off
12. 12
    Sonstigedried under vacuum

Vorschrift

To a solution of 200 mg (0.85 mmol) of methyl 2-acetyl-3-methyl-3-phenylbutanoate in 2 mL of EtOH/AcOH mixture (1:1) are added 249 mg (0.85 mmol) of N-ethyl-6-hydrazino-N-phenylpyridine-3-sulfonamide and the reaction mixture is then heated for 2 hours at 90° C. After concentrating under reduced pressure, the residue is taken up in 100 mL of DCM, washed with 2×30 mL of saturated NaHCO3 solution, dried over Na2SO4, filtered, concentrated under reduced pressure and then purified by chromatography on a column of silica gel, eluting with a cyclohexane/EtOAc gradient of 0 to 20% EtOAc. After concentrating under reduced pressure, 312 mg of a yellow oil are obtained, and are solidified in 20 mL of pentane. The solid obtained is filtered off, and then dried under vacuum. 178 mg of N-ethyl-6-[3-methyl-4-(1-methyl-1-phenylethyl)-5-oxo-2,5-dihydro-1H-pyrazol-1-yl]-N-phenylpyridine-3-sulfonamide are obtained in the form of a white powder.

Quelle