Ethanone, 2-chloro-1,2-diphenyl- → 2-(4,5-Diphenyl-1,3-oxazol-2-ylthio)acetic acid

HRID 1580807

Reaktionsgleichung

Reaktionsgleichung von HRID 1580807
[C:1]1([C:7](=[O:16])[CH:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)Cl)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:17]([S:20][CH2:21][C:22]([OH:24])=[O:23])(=O)[NH2:18]>CN(C=O)C>[C:10]1([C:8]2[N:18]=[C:17]([S:20][CH2:21][C:22]([OH:24])=[O:23])[O:16][C:7]=2[C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Komponenten

4

Edukt 2

HCID 95343Ethanone, 2-chloro-1,2-diphenyl-HCID 23423126(Carbamoylsulfanyl)acetic acid

Produkt 1

HCID 7224662-(4,5-Diphenyl-1,3-oxazol-2-ylthio)acetic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

23 g. of 1,2-diphenyl-2-chloroethanone is heated together with 18 g. of the ethyl ester of carbamoylmercaptoacetic acid in 150 ml. of absolute DMF for 3 hours to 70°. Then, the DMF is removed, and the residue, containing the ethyl ester of N-(1,2-diphenyl-2-oxoethyl)-carbamoylmercaptoacetic acid, is refluxed for 5 hours with a mixture of 100 g. of POCl3 and 200 ml. of benzene. The mixture is then evaporated under reduced pressure and the residue is purified by chromatography on silica gel, thus obtaining the ethyl ester of 4,5-diphenyl-2-oxazolylmercaptoacetic acid, m.p. 54°-56°.

Aufarbeitung

  1. customThen, the DMF is removed
  2. additionthe residue, containing the ethyl ester of N-(1,2-diphenyl-2-oxoethyl)-carbamoylmercaptoacetic acid
  3. temperatureis refluxed for 5 hours with a mixture of 100 g
  4. customThe mixture is then evaporated under reduced pressure
  5. customthe residue is purified by chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-486328458b80444d933e5778ecc0ee94
Quelldatensatz
uspto-grants-1976_01
Patentnummer
US03933840

Verknüpfte Notizen

Wird geladen…