Acetic Anhydride → Ethyl 2-(formylamino)-alpha-oxo-4-thiazoleacetate

HRID 261846

Reaktionsgleichung

Reaktionsgleichung von HRID 261846
C(OC(=O)C)(=[O:3])C.[Mn]([O-])(=O)(=O)=O.[K+].[CH:14]([NH:16][C:17]1[S:18][CH:19]=[C:20]([CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])[N:21]=1)=[O:15]>C(O)(=O)C>[CH:14]([NH:16][C:17]1[S:18][CH:19]=[C:20]([C:22](=[O:3])[C:23]([O:25][CH2:26][CH3:27])=[O:24])[N:21]=1)=[O:15]

Komponenten

6

Edukt 4

HCID 7918Acetic AnhydrideHCID 516875Potassium PermanganateHCID 688091Ethyl 2-formamidothiazol-4-acetateHCID 178470762HCID 178470762, Verbindung

Produkt 1

HCID 2733245Ethyl 2-(formylamino)-alpha-oxo-4-thiazoleacetate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

A mixture of manganous acetate tetrahydrate (120 g.), acetic acid (1000 ml) and acetic anhydride (100 ml.) was stirred for 20 minutes in an oil bath heated at 130° to 135° C., and to the mixture was added potassium permanganate (20 g.) over 5 minutes at 105° to 110° C. with stirring and then the mixture was further stirred for 30 minutes at 130° to 135° C. The mixture was cooled to room temperature, and to the mixture was added ethyl 2-(2-formylaminothiazol-4-yl)acetate, which can be represented as ethyl 2-(2-formylimino-2,3-dihydrothiazol-4-yl)acetate, (53.5 g.), and then the mixture was stirred for 15 hours at 38° to 40° C. under introduction of air at the rate of 6000 ml. per minute. After the reaction, the precipitates were collected by filtration. The precipitates were washed with acetic acid and water in turn and then dried to give ethyl 2-(2-formylaminothiazol-4-yl)glyoxylate, which can be represented as ethyl 2-(2-formylimino-2,3-dihydrothiazol-4-yl)glyoxylate, (41.5 g.), mp 232° to 233° C. (dec.).

Aufarbeitung

  1. temperatureheated at 130° to 135° C.
  2. stirringwith stirring
  3. stirringthe mixture was further stirred for 30 minutes at 130° to 135° C
  4. stirringthe mixture was stirred for 15 hours at 38° to 40° C. under introduction of air at the rate of 6000 ml
  5. customAfter the reaction
  6. filtrationthe precipitates were collected by filtration
  7. washThe precipitates were washed with acetic acid and water in turn
  8. customdried

Quellen und Nachweise

ORD-Eintrag
ord-956308183c314508ae308a709b2925d4
Quelldatensatz
uspto-grants-1979_05
Patentnummer
US04152433

Verknüpfte Notizen

Wird geladen…