Diethyl Ether → Ethyl 2-(2-phenyl-1,3-thiazol-4-yl)acetate

HRID 258576

Reaktionsgleichung

Reaktionsgleichung von HRID 258576
Br[CH2:2][C:3](=O)[CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6].[C:11]([NH2:19])(=[S:18])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.CCOCC>C(O)C>[C:12]1([C:11]2[S:18][CH:2]=[C:3]([CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6])[N:19]=2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Komponenten

5

Edukt 3

HCID 3283Diethyl EtherHCID 575284Ethyl 4-bromo-3-oxobutanoateHCID 683563Thiobenzamide

Produkt 1

HCID 2797666Ethyl 2-(2-phenyl-1,3-thiazol-4-yl)acetate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

Ethyl γ-bromoacetoacetate [2.62 g, 0.9-1.0 mole, described by A. Burger and G. E. Ullyot, J. Org. Chem., 12, 346 (1947)]is added in one portion to a suspension of thiobenzamide [117.5 g, 0.857 mole, described by A. Silberg et al., Ber., 94, 2887 (1961)] in ethanol. The clear solution is refluxed on a steam bath for 2 hr, cooled and slowly added with stirring to ether (3500 ml). The white crystalline precipitate is collected, washed with ether and partitioned between water and ether. Sodium bicarbonate is added in portions until the mixture is alkaline. The mixture is extracted with ether, the ether solution is washed with saturated sodium chloride solution, dried, and evaporated to give ethyl 2-phenylthiazole-4-acetate (VII; R1 = H, R9 = CH2CH3), γmaxCHCl3 1725 cm-1.

Aufarbeitung

  1. temperatureThe clear solution is refluxed on a steam bath for 2 hr
  2. temperaturecooled
  3. additionslowly added
  4. customThe white crystalline precipitate is collected
  5. washwashed with ether
  6. custompartitioned between water and ether
  7. additionSodium bicarbonate is added in portions until the mixture
  8. extractionThe mixture is extracted with ether
  9. washthe ether solution is washed with saturated sodium chloride solution
  10. customdried
  11. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-2964eaeb2c594e1793a3fd1e6a96a762
Quelldatensatz
uspto-grants-1977_07
Patentnummer
US04033977

Verknüpfte Notizen

Wird geladen…