Water → HCID 178482475, Verbindung

HRID 1620485Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1620485
[F:1][C:2]([F:21])([F:20])[C:3]1[CH:15]=[C:14]([C:16]([F:19])([F:18])[F:17])[CH:13]=[CH:12][C:4]=1[CH2:5][N:6]1[CH2:9][CH:8]([CH:10]=O)[CH2:7]1.[CH3:22][NH:23][C:24]1[CH2:28][S:27][C:26](=[O:29])[N:25]=1.CC(C)([O-])C.[K+].O>C(O)C>[F:21][C:2]([F:1])([F:20])[C:3]1[CH:15]=[C:14]([C:16]([F:19])([F:18])[F:17])[CH:13]=[CH:12][C:4]=1[CH2:5][N:6]1[CH2:9][CH:8](/[CH:10]=[C:28]2/[C:24]([NH:23][CH3:22])=[N:25][C:26](=[O:29])[S:27]/2)[CH2:7]1

Komponenten

6

Edukt 4

HCID 962WaterHCID 23665647Potassium tert-butoxideHCID 866786761-[2,4-Bis(trifluoromethyl)benzyl]azetidine-3-carbaldehydeHCID 178482466HCID 178482466, Verbindung

Produkt 1

HCID 178482475HCID 178482475, VerbindungAusbeute 9,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

To a solution of 1-[2,4-bis(trifluoromethyl)benzyl]azetidine-3-carbaldehyde (90 mg) and 4-(methylamino)-1,3-thiazol-2(5H)-one (38 mg) in ethanol (3 mL) was added potassium tert-butoxide (32 mg) at room temperature, and the mixture was stirred with heating under reflux for 3 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (12 mg).

Aufarbeitung

  1. temperaturewith heating
  2. temperatureunder reflux for 3 hr
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-4b3f2c3aeb2341f3b1d6e457450981e1
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08772277B2

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