Reaktion #1103784

Reaktionsgleichung

3-(4-chlorophenyl)-4,5-dihydro-4-phenyl-1H-pyrazole

3-(4-chlorophenyl)-4,5-dihydro-4-phenyl-1H-pyrazole

[(4-chlorophenyl)sulfonyl]dithioimidocarbonic acid dimethyl ester

triethylamine

→

3-(4-chlorophenyl)-N-((4-chlorophenyl)sulfonyl)-4,5-dihydro-4-phenyl-1H-pyrazole-1-carboximidothioic acid methyl ester

Ausbeute 80.0%

Lösungsmittel

acetonitrile

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturwas heated
2. 2
   Temperaturat reflux temperature for 20 hours
3. 3
   Temperaturthe resulting mixture was heated
4. 4
   Temperaturat reflux temperature for another 16 hours
5. 5
   EinengenAfter concentration in vacuo, dichloromethane
6. 6
   workup.ADDITIONwas added
7. 7
   Waschenthe resulting solution was washed twice with water
8. 8
   Trocknendried over anhydrous Na2SO4
9. 9
   FiltrationAfter filtration and evaporation in vacuo the residue
10. 10
    Sonstigewas further purified by flash chromatography (diethyl ether/petroleum ether=1/1 (v/v))

Vorschrift

Part A: A stirred mixture of 3-(4-chlorophenyl)-4,5-dihydro-4-phenyl-1H-pyrazole (12.0 gram, 46.8 mmol), [(4-chlorophenyl)sulfonyl]dithioimidocarbonic acid dimethyl ester (CAS: 13068-12-7) (9.20 gram, 31.1 mmol) and triethylamine (15 ml) in acetonitrile (200 ml) was heated at reflux temperature for 20 hours. An additional portion of 3-(4-chlorophenyl)-4,5-dihydro-4-phenyl-1H-pyrazole (12.0 gram, 46.8 mmol) was added and the resulting mixture was heated at reflux temperature for another 16 hours. After concentration in vacuo, dichloromethane was added and the resulting solution was washed twice with water and dried over anhydrous Na2SO4. After filtration and evaporation in vacuo the residue was further purified by flash chromatography (diethyl ether/petroleum ether=1/1 (v/v)) to give 3-(4-chlorophenyl)-N-((4-chlorophenyl)sulfonyl)-4,5-dihydro-4-phenyl-1H-pyrazole-1-carboximidothioic acid methyl ester (12.5 gram, 80% yield based on [(4-chlorophenyl)sulfonyl]dithioimidocarbonic acid dimethyl ester) as an amorphous solid.

Quelle