Sodium Carbonate → 4-Thiazolecarboxylic acid, 5-phenyl-2-(trifluoromethyl)-, ethyl ester

HRID 383927

Reaktionsgleichung

Reaktionsgleichung von HRID 383927
Cl[CH:2]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:3](=O)[C:4]([O:6][CH2:7][CH3:8])=[O:5].[F:16][C:17]([F:22])([F:21])[C:18]([NH2:20])=[S:19].C([O-])([O-])=O.[Na+].[Na+]>CC#N>[C:10]1([C:2]2[S:19][C:18]([C:17]([F:22])([F:21])[F:16])=[N:20][C:3]=2[C:4]([O:6][CH2:7][CH3:8])=[O:5])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Komponenten

5

Edukt 3

HCID 10340Sodium CarbonateHCID 4425751TrifluoroethanethioamideHCID 13833360Ethyl 3-chloro-2-oxo-3-phenylpropanoate

Produkt 1

HCID 592913484-Thiazolecarboxylic acid, 5-phenyl-2-(trifluoromethyl)-, ethyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

A solution of ethyl 3-chloro-2-oxo-3-phenylpropanoate and trifluorothioacetamide in MeCN was heated under reflux. To the reaction mixture was added an aqueous Na2CO3 solution, followed by extraction with EtOAc. The organic layer was washed with water and brine in this order, dried, and then concentrated under reduced pressure. The residue was purified by medium-pressure preparative liquid chromatography (silica gel, YAMAZEN YFLC WPrep2XY, hexane: EtOAc) to obtain ethyl 5-phenyl-2-(trifluoromethyl)-1,3-thiazole-4-carboxylate as a white solid.

Aufarbeitung

  1. temperatureunder reflux
  2. extractionfollowed by extraction with EtOAc
  3. washThe organic layer was washed with water and brine in this order
  4. customdried
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by medium-pressure preparative liquid chromatography (silica gel, YAMAZEN YFLC WPrep2XY, hexane: EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-4aba71c0bc784a9fb07d98cc7ee5226f
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08367696B2

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