Dimethyl Sulfoxide → 1-(4-Chlorophenyl)-5-methyl-N-[4-(4-morpholinopiperidin-1-yl)-3-nitrophenyl]pyrazole-4-carboxamide

HRID 1744634

Reaktionsgleichung

Reaktionsgleichung von HRID 1744634
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]([CH3:13])=[C:11]([C:14]([NH:16][C:17]3[CH:22]=[CH:21][C:20](Cl)=[C:19]([N+:24]([O-:26])=[O:25])[CH:18]=3)=[O:15])[CH:10]=[N:9]2)=[CH:4][CH:3]=1.[O:27]1[CH2:32][CH2:31][N:30]([CH:33]2[CH2:38][CH2:37][NH:36][CH2:35][CH2:34]2)[CH2:29][CH2:28]1.CS(C)=O>O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]([CH3:13])=[C:11]([C:14]([NH:16][C:17]3[CH:22]=[CH:21][C:20]([N:36]4[CH2:37][CH2:38][CH:33]([N:30]5[CH2:31][CH2:32][O:27][CH2:28][CH2:29]5)[CH2:34][CH2:35]4)=[C:19]([N+:24]([O-:26])=[O:25])[CH:18]=3)=[O:15])[CH:10]=[N:9]2)=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 679Dimethyl SulfoxideHCID 7957244-MorpholinopiperidineHCID 222280911-(4-Chlorophenyl)-N-(4-chloro-3-nitrophenyl)-5-methylpyrazole-4-carboxamide

Produkt 1

HCID 222279621-(4-Chlorophenyl)-5-methyl-N-[4-(4-morpholinopiperidin-1-yl)-3-nitrophenyl]pyrazole-4-carboxamideAusbeute 32,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

1-(4-Chlorophenyl)-N-(4-chloro-3-nitrophenyl)-5-methylpyrazole-4-carboxamide (1.6 g) and 4-morpholinopiperidine (2.4 g) were added to dimethyl sulfoxide (20 ml) and the mixture was stirred at a refluxing temperature for 1.5 h. After cooling to room temperature, water was added and the precipitated solid was collected by filtration and extracted with chloroform. The organic layer was washed with 30% potassium carbonate and saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (mobile phase:chloroform/methanol) and recrystallized from hydrous dimethylformamide to give the title compound (0.7 g), melting point: 195–200° C.

Aufarbeitung

  1. filtrationthe precipitated solid was collected by filtration
  2. extractionextracted with chloroform
  3. washThe organic layer was washed with 30% potassium carbonate and saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (mobile phase:chloroform/methanol)
  7. customrecrystallized from hydrous dimethylformamide

Quellen und Nachweise

ORD-Eintrag
ord-6a2e29d848ec43788404ae9cea6b8b6c
Quelldatensatz
uspto-grants-2006_03
Patentnummer
US07015218B1

Verknüpfte Notizen

Wird geladen…