Pyridine → 2-Bromo-4-propionamidothiazole

HRID 26198

Reaktionsgleichung

Reaktionsgleichung von HRID 26198
Br.[NH2:2][C:3]1[N:4]=[C:5]([Br:8])[S:6][CH:7]=1.N1C=C[CH:12]=[CH:11][CH:10]=1.C([O-])(=[O:17])C.[Na+]>C(OC(=O)CC)(=O)CC>[Br:8][C:5]1[S:6][CH:7]=[C:3]([NH:2][C:10](=[O:17])[CH2:11][CH3:12])[N:4]=1

Komponenten

5

Edukt 3

HCID 1049PyridineHCID 517045Sodium AcetateHCID 202940412-Bromo-1,3-thiazol-4-amine--hydrogen bromide (1/1)

Produkt 1

HCID 202940462-Bromo-4-propionamidothiazoleAusbeute 11,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 31263Propionic anhydrideLösungsmittel

Versuchsvorschrift

4-Amino-2-bromothiazole hydrobromide (6.5g) was suspended in propionic anhydride (25 ml.) with stirring; then treated with pyridine (12.5 ml.) over 15 minutes, maintaining reaction temperature at 0° C. with an ice bath. After the addition was complete, the reaction mixture was stirred for 2 hours at room temperature, then poured onto 20% aqueous sodium acetate (250 ml.) and stirred for 30 minutes. The precipitate was removed by filtration and washed with water. The solid was air dried and extracted with hexane, in a Soxhlet apparatus. The hexane was cooled and the crystals collected and recrystallised to give the title compound (2.8 g.) m.p. 122°-5° C. (Found: C, 31.1; H, 3.1; N, 11.9. C6H7BrN2OS requires C, 30.7; H, 3.0; N, 11.9%).

Aufarbeitung

  1. temperaturemaintaining
  2. customreaction temperature at 0° C. with an ice bath
  3. additionAfter the addition
  4. stirringthe reaction mixture was stirred for 2 hours at room temperature
  5. stirringstirred for 30 minutes
  6. customThe precipitate was removed by filtration
  7. washwashed with water
  8. customdried
  9. extractionextracted with hexane, in a Soxhlet apparatus
  10. temperatureThe hexane was cooled
  11. customthe crystals collected
  12. customrecrystallised

Quellen und Nachweise

ORD-Eintrag
ord-eb0201cba78f4dffbe44d3aa8f97630d
Quelldatensatz
uspto-grants-1979_04
Patentnummer
US04148904

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