Acetic Anhydride → 2-Bromo-4-formamidothiazole

HRID 26202

Reaktionsgleichung

Reaktionsgleichung von HRID 26202
C(O[C:5](=[O:7])C)(=O)C.C(OC=O)(=O)C.Br.[NH2:15][C:16]1[N:17]=[C:18]([Br:21])[S:19][CH:20]=1.C([O-])(=O)C.[Na+]>N1C=CC=CC=1.C(O)=O>[Br:21][C:18]1[S:19][CH:20]=[C:16]([NH:15][CH:5]=[O:7])[N:17]=1

Komponenten

7

Edukt 4

HCID 7918Acetic AnhydrideHCID 75269Acetic-formic anhydrideHCID 517045Sodium AcetateHCID 202940412-Bromo-1,3-thiazol-4-amine--hydrogen bromide (1/1)

Produkt 1

HCID 202940362-Bromo-4-formamidothiazoleAusbeute 58 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 284Formic AcidLösungsmittelHCID 1049PyridineLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

Acetic anhydride (100 ml) was cooled to 0° C. and treated with 98% formic acid (50 ml.). The resulting mixture was heated at 50° C. for 15 minutes then cooled to 0° C. To this solution of formic-acetic anhydride was added 4-amino-2-bromothiazole hydrobromide (26 g, 0.1 m) followed dropwise by pyridine (25 ml.). The reaction mixture was allowed to stand for 1 hour at room temperature then poured onto 20% aqueous sodium acetate solution (500 ml). The resulting crystals were removed by filtration, washed once with water (100 ml) then recrystallised from ethanol to give the 2-bromo-4-formamidothiazole (12 g, 58%). m.p. 167° C. d. (Found: C, 23.55; H, 1.6; N, 13.45. C4H3N2BrOS requires C, 23.2; H, 1.45; N, 13.5%).

Aufarbeitung

  1. temperaturethen cooled to 0° C
  2. customThe resulting crystals were removed by filtration
  3. washwashed once with water (100 ml)
  4. customthen recrystallised from ethanol

Quellen und Nachweise

ORD-Eintrag
ord-ce3c772025cf4b678f7c457c13f2cb42
Quelldatensatz
uspto-grants-1979_04
Patentnummer
US04148904

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