Water → HCID 59291484, Verbindung

HRID 383930Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 383930
N[C:2]1[S:3][C:4]([C:12]2[C:17]([F:18])=[CH:16][CH:15]=[CH:14][C:13]=2[F:19])=[C:5]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[N:6]=1.[N+]([O-])(OC(C)(C)C)=O.O.CCOC(C)=O>C1COCC1>[F:18][C:17]1[CH:16]=[CH:15][CH:14]=[C:13]([F:19])[C:12]=1[C:4]1[S:3][CH:2]=[N:6][C:5]=1[C:7]([O:9][CH2:10][CH3:11])=[O:8]

Komponenten

6

Edukt 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 164756Nitric acid, 1,1-dimethylethyl esterHCID 59291235HCID 59291235, Verbindung

Produkt 1

HCID 59291484HCID 59291484, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of ethyl 2-amino-5-(2,6-difluorophenyl)-1,3-thiazole-4-carboxylate in THF was slowly added dropwise tert-butyl nitrate under heating under reflux. After completion of dropwise addition, it was further stirred at the same temperature for 4 hours. The reaction mixture was cooled to room temperature, followed by addition of water and extraction with EtOAc. The organic layer was washed with brine, dried, and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:EtOAc=9:1-7:3) to obtain ethyl 5-(2,6-difluorophenyl)-1,3-thiazole-4-carboxylate as a yellow oily substance.

Aufarbeitung

  1. temperatureunder heating
  2. temperatureunder reflux
  3. additionAfter completion of dropwise addition, it
  4. washThe organic layer was washed with brine
  5. customdried
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (hexane:EtOAc=9:1-7:3)

Quellen und Nachweise

ORD-Eintrag
ord-59f4527d7dd34a4f91a455f83fc0bfa1
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08367696B2

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