Pyridine → Benzeneacetamide

HRID 35733

Reaktionsgleichung

Reaktionsgleichung von HRID 35733
N1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:7](Br)(=O)C.[CH3:11]/[C:12](/[O:18][Si](C)(C)C)=[N:13]\[Si](C)(C)C.C[Si](C)(C)NS(N[Si](C)(C)C)(=O)=O>O1CCOCC1>[C:2]1([CH2:11][C:12]([NH2:13])=[O:18])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

6

Edukt 4

HCID 1049PyridineHCID 10482Acetyl bromideHCID 6913588N,O-bis(trimethylsilyl)acetamideHCID 13813126N,N'-bis(trimethylsilyl)sulfamide

Produkt 1

HCID 7680Benzeneacetamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

0.36 ml (4.5 mmoles) of pyridine were added to a suspension of 0.525 g (1.50 mmoles) of benzylpenicillin sulphoxide in 10 ml of dioxane and the resulting solution was cooled to 0° C. followed by the addition of 0.05 ml (0.5 mmole) of acetyl bromide and the reaction mixture was stirred for 30 minutes at 0° C. 0.49 ml (1.9 mmoles) of N,O-bis(trimethylsilyl)acetamide and 0.38 g (1.6 mmoles) of N,N'-bis-trimethylsilyl sulphamide were added. The mixture was heated to reflux and after 4 hours at reflux, the amount of Δ3 -phenylacetamide desacetoxycephalosporanic acid formed, titrated by a microbiological analysis, was 95%.

Aufarbeitung

  1. temperatureThe mixture was heated
  2. temperatureto reflux and after 4 hours
  3. temperatureat reflux

Quellen und Nachweise

ORD-Eintrag
ord-acb465f73b04489bbec5774333ac010e
Quelldatensatz
uspto-grants-1988_08
Patentnummer
US04767851

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