Dimethyl Sulfoxide → N-(3,4-Dimethylisoxazol-5-yl)-4-(5-phenyl-1,3,4-oxadiazol-2-yl)piperidine-1-carboxamide

HRID 2263331Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2263331
[CH3:1][C:2]1[C:6]([CH3:7])=[C:5]([NH:8][C:9](=[O:16])OCC(Cl)(Cl)Cl)[O:4][N:3]=1.[C:17]1([C:23]2[O:27][C:26]([CH:28]3[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]3)=[N:25][N:24]=2)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C(N(C(C)C)CC)(C)C.CS(C)=O>O>[CH3:1][C:2]1[C:6]([CH3:7])=[C:5]([NH:8][C:9]([N:31]2[CH2:30][CH2:29][CH:28]([C:26]3[O:27][C:23]([C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=4)=[N:24][N:25]=3)[CH2:33][CH2:32]2)=[O:16])[O:4][N:3]=1

Komponenten

6

Edukt 4

HCID 679Dimethyl SulfoxideHCID 81531DiisopropylethylamineHCID 27611504-(5-Phenyl-1,3,4-oxadiazol-2-yl)piperidineHCID 862452572,2,2-Trichloroethyl(3,4-dimethylisoxazol-5-yl)carbamate

Produkt 1

HCID 59594508N-(3,4-Dimethylisoxazol-5-yl)-4-(5-phenyl-1,3,4-oxadiazol-2-yl)piperidine-1-carboxamideAusbeute 37,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

A solution of 2,2,2-trichloroethyl (3,4-dimethylisoxazol-5-yl)carbamate (293 mg, 1.02 mmol), 4-(5-phenyl-1,3,4-oxadiazol-2-yl)piperidine (234 mg, 1.02 mmol), diisopropylethylamine (0.387 ml, 2.05 mmol) and dimethyl sulfoxide (4 ml) was stirred at 70° C. for 12 hours, the reaction mixture was poured into water, and the mixture was extracted with ethyl acetate. The extract was washed with water, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was recrystallized from ethyl acetate to give 142 mg (37.9%) of the desired product as a solid.

Aufarbeitung

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationThe solvent was distilled off under reduced pressure
  5. customthe residue was recrystallized from ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-be87a3b985334a2b9dfd0ea492cf4bad
Quelldatensatz
uspto-grants-2010_12
Patentnummer
US07851473B2

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