Dimethyl Sulfoxide → N-Isoxazol-5-yl-4-(4-phenyl-1,3-thiazol-2-yl)piperazine-1-carboxamide

HRID 2263092Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2263092
[O:1]1[C:5]([NH:6][C:7](=[O:14])OCC(Cl)(Cl)Cl)=[CH:4][CH:3]=[N:2]1.[C:15]1([C:21]2[N:22]=[C:23]([N:26]3[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]3)[S:24][CH:25]=2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(N(C(C)C)CC)(C)C.CS(C)=O>O>[O:1]1[C:5]([NH:6][C:7]([N:29]2[CH2:30][CH2:31][N:26]([C:23]3[S:24][CH:25]=[C:21]([C:15]4[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=4)[N:22]=3)[CH2:27][CH2:28]2)=[O:14])=[CH:4][CH:3]=[N:2]1

Komponenten

6

Edukt 4

HCID 679Dimethyl SulfoxideHCID 81531DiisopropylethylamineHCID 7124681-(4-Phenyl-1,3-thiazol-2-yl)piperazineHCID 687764112,2,2-Trichloroethyl isoxazol-5-ylcarbamate

Produkt 1

HCID 68778074N-Isoxazol-5-yl-4-(4-phenyl-1,3-thiazol-2-yl)piperazine-1-carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

A solution of 2,2,2-trichloroethyl isoxazol-5-ylcarbamate (200 mg, 0.771 mmol), 1-(4-phenyl-1,3-thiazol-2-yl)piperazine (189 mg, 0.771 mmol), diisopropylethylamine (0.134 ml, 0.771 mmol) and dimethylsulfoxide (7 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. The residue was purified by silica gel column chromatography (ethyl acetate) to obtain the desired product as a solid. This was recrystallized from a mixed solvent of ethyl acetate and hexane to obtain the desired product (98.8 mg, 36.1%) 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 purified by silica gel column chromatography (ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-c974ec2f109c4d4a86a6aef67263cee2
Quelldatensatz
uspto-grants-2010_12
Patentnummer
US07851473B2

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