Water → 4-[4-(3-Chlorophenyl)-1,3-thiazol-2-yl]-N-(3,4-dimethylisoxazol-5-yl)piperazine-1-carboxamide

HRID 2263307Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2263307
[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.[Cl:17][C:18]1[CH:19]=[C:20]([C:24]2[N:25]=[C:26]([N:29]3[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]3)[S:27][CH:28]=2)[CH:21]=[CH:22][CH:23]=1.C(N(C(C)C)CC)(C)C.O>CS(C)=O>[Cl:17][C:18]1[CH:19]=[C:20]([C:24]2[N:25]=[C:26]([N:29]3[CH2:30][CH2:31][N:32]([C:9]([NH:8][C:5]4[O:4][N:3]=[C:2]([CH3:1])[C:6]=4[CH3:7])=[O:16])[CH2:33][CH2:34]3)[S:27][CH:28]=2)[CH:21]=[CH:22][CH:23]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 617805201-[4-(3-Chlorophenyl)-1,3-thiazol-2-yl]piperazineHCID 862452572,2,2-Trichloroethyl(3,4-dimethylisoxazol-5-yl)carbamate

Produkt 1

HCID 115099494-[4-(3-Chlorophenyl)-1,3-thiazol-2-yl]-N-(3,4-dimethylisoxazol-5-yl)piperazine-1-carboxamideAusbeute 41,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

A mixture of 2,2,2-trichloroethyl (3,4-dimethylisoxazol-5-yl)carbamate (226 mg, 0.786 mmol), 1-[4-(3-chlorophenyl)-1,3-thiazol-2-yl]piperazine (200 mg, 0.715 mmol) and diisopropylethylamine (0.249 ml, 1.43 mmol) in dimethyl sulfoxide (2.5 ml) was stirred at 70° C. for 15 hours. Water was poured to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with water, and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:1), and recrystallized from a mixed solvent of hexane and ethyl acetate to give 124 mg (41.4%) of the desired product as a solid. mp 201-202° C.

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)
  6. customrecrystallized from a mixed solvent of hexane and ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-52cd1eb15dbc4d5b87078b7498c1fbb3
Quelldatensatz
uspto-grants-2010_12
Patentnummer
US07851473B2

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