Reaktion #545277

Reaktionsgleichung

Thionyl chloride

4-hydroxy-6-iodo-7-fluoro-quinazoline

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title compound

Ausbeute 67.0%

4-Chloro-6-iodo-7-fluoro-quinazoline hydrochloride

Ausbeute 67.0%

Lösungsmittel

dimethylformamide

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigefitted with a magnetic stir bar
2. 2
   Temperaturheated to
3. 3
   Temperatura gentle reflux for 24 hours
4. 4
   Temperaturto cool
5. 5
   Einengenby concentrating the reaction mixture to a thick yellowish residue
6. 6
   workup.ADDITIONTo this residue was added dichloromethane (0.1 liter) and toluene (0.1 liter)
7. 7
   EinengenThe mixture was concentrated to dryness
8. 8
   workup.ADDITIONTo the resulting solid was added 0.5 liters of dry dichloromethane
9. 9
   FiltrationThe mixture was filtered
10. 10
    Waschenthe remaining solids were washed with minimal dichloromethane
11. 11
    Einengenconcentrated to a solid
12. 12
    Sonstigedried under vacuum at room temperature

Vorschrift

Thionyl chloride (0.6 liters), 4-hydroxy-6-iodo-7-fluoro-quinazoline (36 grams, 124 mmoles), and dimethylformamide (6 ml) were combined in a one liter one-neck flask fitted with a magnetic stir bar. The mixture was placed under anhydrous nitrogen and heated to a gentle reflux for 24 hours. The mixture was allowed to cool, followed by concentrating the reaction mixture to a thick yellowish residue. To this residue was added dichloromethane (0.1 liter) and toluene (0.1 liter). The mixture was concentrated to dryness. This procedure was repeated two additional times. To the resulting solid was added 0.5 liters of dry dichloromethane and the mixture was stirred for one hour. The mixture was filtered and the remaining solids were washed with minimal dichloromethane. The dichoromethane filtrates were combined, concentrated to a solid, and dried under vacuum at room temperature to yield 28.6 grams (67%) of the title compound. 1H NMR (400 MHz, CDCl3-d1) δ: 9.03 (s, 1H), 8.76 (d, 1H), 7.69 (d, 1H). ESI-MS m/z 309 (M+1).

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