Dimethyl Sulfoxide → N-1,2-Benzisoxazol-3-yl-4-(4-phenyl-2-thienyl)piperazine-1-carboxamide

HRID 2263055Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2263055
[C:1]1([C:7]2[CH:8]=[C:9]([N:12]3[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]3)[S:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[O:18]1[C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=2[C:20]([N:27](C(OCC(Cl)(Cl)Cl)=O)[C:28](OCC(Cl)(Cl)Cl)=[O:29])=[N:19]1.C(N(C(C)C)CC)(C)C.CS(C)=O>O>[O:18]1[C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=2[C:20]([NH:27][C:28]([N:15]2[CH2:16][CH2:17][N:12]([C:9]3[S:10][CH:11]=[C:7]([C:1]4[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=4)[CH:8]=3)[CH2:13][CH2:14]2)=[O:29])=[N:19]1

Komponenten

6

Edukt 4

HCID 679Dimethyl SulfoxideHCID 81531DiisopropylethylamineHCID 687773121-(4-Phenyl-2-thienyl)piperazineHCID 86625471Bis(2,2,2-trichloroethyl) 1,2-benzisoxazol-3-ylimidodicarbonate

Produkt 1

HCID 68779482N-1,2-Benzisoxazol-3-yl-4-(4-phenyl-2-thienyl)piperazine-1-carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

A solution of 1-(4-phenyl-2-thienyl)piperazine (240 mg, 0.984 mmol), bis(2,2,2-trichloroethyl) 1,2-benzisoxazol-3-ylimidodicarbonate (239 mg, 0.492 mmol), diisopropylethylamine (0.0857 ml, 0.492 mmol) and dimethylsulfoxide (3 ml) was stirred at 70° C. for 2 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 (hexane:ethyl acetate=1:1) 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 (42.5 mg, 21.4%) 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 (hexane:ethyl acetate=1:1)

Quellen und Nachweise

ORD-Eintrag
ord-f20fc80628b34866bd9f2eca4bc2389a
Quelldatensatz
uspto-grants-2010_12
Patentnummer
US07851473B2

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