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

HRID 649128

Reaktionsgleichung

Reaktionsgleichung von HRID 649128
[NH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][NH:3][C:2]1=[S:11].Cl[CH2:13][C:14](O)=[O:15].C(=O)(O)[O-].[Na+].CN(C)C=O>O>[S:11]1[C:2]2=[N:1][C:10]3[C:5]([CH2:4][N:3]2[C:14](=[O:15])[CH2:13]1)=[CH:6][CH:7]=[CH:8][CH:9]=3

Komponenten

6

Edukt 4

HCID 300Chloroacetic AcidHCID 6228DimethylformamideHCID 516892Sodium BicarbonateHCID 36448543,4-dihydro-1H-quinazoline-2-thione2×

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

A mixture of 1.0 g (0.006 mol) 3,4-dihydro-2(1H)-quinazolinethione (compound II), 0.57 g (0.006 mol) chloroacetic acid, and 0.54 g (0.0065 mol) sodium bicarbonate is mixed in 31.25 ml water, and heated overnight at 90° C. Then, 12.5 ml of dimethylformamide is added, and the reaction mixture is refluxed for 61/2 hours. After cooling, 5H-thiazolo[2,3-b]quinazolin-3(2H)-one, as the precipitated solid, is filtered off and recrystallized from anhydrous ethanol. Replacement of 3,4-dihydro-2(1H)-quinazolinethione by a derivative thereof in which a nuclear hydrogen of the benzene ring has been substituted with lower alkyl, alkoxy, halogen, trifluoromethyl, NO2 or NH2, results in the corresponding derivative of 5H-thiazolo[2,3-b]quinazolin-3(2H)-one.

Aufarbeitung

  1. temperaturethe reaction mixture is refluxed for 61/2 hours
  2. temperatureAfter cooling
  3. filtration5H-thiazolo[2,3-b]quinazolin-3(2H)-one, as the precipitated solid, is filtered off
  4. customrecrystallized from anhydrous ethanol

Quellen und Nachweise

ORD-Eintrag
ord-d88c7e9f43e444bfb87d19495a225fda
Quelldatensatz
uspto-grants-1988_04
Patentnummer
US04738964

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