Acetic Acid → 5H-thiazolo(2,3-b)quinazolin-3(2H)-one

HRID 280372

Reaktionsgleichung

Reaktionsgleichung von HRID 280372
[BH4-].[Na+].[Te].C(O)(=O)C.C(N(CC1C=CC=CC=1)C(=O)C=[C:15]1[S:27][C:18]2=[N:19][C:20]3[C:25]([CH2:26][N:17]2[C:16]1=[O:28])=[CH:24][CH:23]=[CH:22][CH:21]=3)(C)(C)C>C(O)C>[O:28]=[C:16]1[N:17]2[C:18](=[N:19][C:20]3[C:25]([CH2:26]2)=[CH:24][CH:23]=[CH:22][CH:21]=3)[S:27][CH2:15]1

Komponenten

6

Edukt 4

HCID 176Acetic AcidHCID 4311764Sodium borohydrideHCID 6327182TelluriumHCID 53873445N-tert-butyl-N-benzyl(3-oxo-5H-thiazolo[2,3-b]quinazolin-2(3H)-ylidene)acetamide

Produkt 1

HCID 50984915H-thiazolo(2,3-b)quinazolin-3(2H)-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel3×

Reaktionsbedingungen

Temperatur
-20 °C

Versuchsvorschrift

A suspension of sodium borohydride (0.08 mol) and tellurium powder (0.034 mol) in 135 ml of anhydrous ethanol is heated under nitrogen atmosphere, preferably for about 15 min. After cooling to -20° C., 8.08 ml glacial acetic acid in 33.65 ml anhydrous ethanol solution (8.08:33.65 v/v) is added dropwise, and the mixture is stirred at -20° C. for 5 min. Stirring is followed by the addition of 0.013 mol of a substituted 2,3-dihydro-5H-thiazol[2,3-b]quinazoline derivative, synthesized by the procedures in the preceding sections (2) to (5), and dissolved in 13.5 ml anhydrous ethanol. The reaction mixture is allowed to warm up to ambient temperature and stirred for about 10 hours. The mixture is filtered through celite, and evaporated under reduced pressure. The residue is taken up in water and extracted with chloroform. The organic extract is dried over anhydrous magnesium sulfate and evaporated under reduced pressure, yielding the corresponding 2,3-dihydro-3-oxo-5H-thiazolo[2,3-b]quinazoline derivative with a saturated exocyclic bond at the 2 position of the 2,3-dihydro-5-thiazo[2,3-b]quinazoline moiety.

Aufarbeitung

  1. temperatureis heated under nitrogen atmosphere, preferably for about 15 min
  2. stirringStirring
  3. temperatureto warm up to ambient temperature
  4. stirringstirred for about 10 hours
  5. filtrationThe mixture is filtered through celite
  6. customevaporated under reduced pressure
  7. extractionextracted with chloroform
  8. extractionThe organic extract
  9. dry with materialis dried over anhydrous magnesium sulfate
  10. customevaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-c5b505ccd7f64b12a92ee76480d6b526
Quelldatensatz
uspto-grants-1986_05
Patentnummer
US04588812

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