Ethyl bromopyruvate → Ethyl 2-(phenylamino)-4-thiazolecarboxylate

HRID 2107259Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2107259
[C:1]1([NH:7][C:8]([NH2:10])=[S:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[CH2:12][C:13](=O)[C:14]([O:16][CH2:17][CH3:18])=[O:15]>C(O)C>[NH:7]([C:8]1[S:9][CH:12]=[C:13]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[N:10]=1)[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Komponenten

4

Edukt 2

HCID 66144Ethyl bromopyruvateHCID 676454Phenylthiourea

Produkt 1

HCID 15053537Ethyl 2-(phenylamino)-4-thiazolecarboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A mixture comprising 8.6 g of phenylthiourea, 10 g of ethyl bromopyruvate and 100 ml of ethanol was heated under reflux for 3 hours, and the reaction mixture was then concentrated under reduced pressure. A saturated aqueous sodium hydrogen carbonate solution was added to the residue, followed by extraction with ethyl acetate. The extract was dried over anhydrous sodium sulfate and evaporated under reduced pressure. The crystals which formed were collected by filtration. washed with benzene, and then recrystallized from ethanol, giving the desired compound as pale yellow prismatic crystals.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureunder reflux for 3 hours
  3. concentrationthe reaction mixture was then concentrated under reduced pressure
  4. additionA saturated aqueous sodium hydrogen carbonate solution was added to the residue
  5. extractionfollowed by extraction with ethyl acetate
  6. dry with materialThe extract was dried over anhydrous sodium sulfate
  7. customevaporated under reduced pressure
  8. customThe crystals which formed
  9. filtrationwere collected by filtration
  10. washwashed with benzene
  11. customrecrystallized from ethanol

Quellen und Nachweise

ORD-Eintrag
ord-ea8ac3e93ee34a57b5ef4f1bed6fe4e6
Quelldatensatz
uspto-grants-1990_06
Patentnummer
US04933355

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