Dimethylformamide → 4,5-Diphenyl-2-oxazolyl mercaptoacetic acid

HRID 2072545

Reaktionsgleichung

Reaktionsgleichung von HRID 2072545
[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([S:20][CH2:21][C:22]([OH:24])=[O:23])(=O)N.[CH3:25][N:26](C=O)C>>[C:10]1([C:8]2[N:26]=[C:25]([CH:21]([SH:20])[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 3

HCID 6228DimethylformamideHCID 95343Ethanone, 2-chloro-1,2-diphenyl-HCID 23423126(Carbamoylsulfanyl)acetic acid

Produkt 1

HCID 214083604,5-Diphenyl-2-oxazolyl mercaptoacetic acid

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-oxazolyl-mercaptoacetic 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-156f575e82c1420193bc723d5471a5db
Quelldatensatz
uspto-grants-1977_09
Patentnummer
US04051250

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