Ethyl bromopyruvate → Ethyl 2-(trifluoromethyl)-1,3-thiazole-4-carboxylate

HRID 1054225

Reaktionsgleichung

Reaktionsgleichung von HRID 1054225
[CH2:1]([NH:3][C:4](=[S:9])[C:5]([F:8])([F:7])[F:6])[CH3:2].[CH3:10][CH2:11][O:12][C:13](C(CBr)=O)=[O:14]>C1COCC1.O.C(Cl)Cl>[F:6][C:5]([F:8])([F:7])[C:4]1[S:9][CH:2]=[C:1]([C:13]([O:12][CH2:11][CH3:10])=[O:14])[N:3]=1

Komponenten

6

Edukt 2

HCID 66144Ethyl bromopyruvateHCID 15499429N-Ethyl(trifluoro)ethanethioamide

Produkt 1

HCID 20079591Ethyl 2-(trifluoromethyl)-1,3-thiazole-4-carboxylateAusbeute 42 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
95 °C

Versuchsvorschrift

To a stirring solution of ethyl 2,2,2-trifluoroethanethioamide (0.35 g, 2.71 mmol) in THF (12 ml) was added ethyl bromo pyruvate (0.375 ml, 2.98 mmol) at RT. Reaction mixture was heated at 90-100° C. for 16 h. Reaction mixture was diluted with water and DCM. The organic layer was separated and distilled out to get crude product which was column purified using 0-2% EtOAC in hexane to get titled compound in 42% yield.

Aufarbeitung

  1. customReaction mixture
  2. customReaction mixture
  3. customThe organic layer was separated
  4. distillationdistilled out
  5. customto get crude product which
  6. custompurified

Quellen und Nachweise

ORD-Eintrag
ord-448485750cbc4c689cacf333ad9151b2
Quelldatensatz
uspto-grants-2016_07
Patentnummer
US09394300B2

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