Reaktion #507199

Reaktionsgleichung

4-iodo-N-(2-hydroxyphenyl)benzamide

para-toluenesulfonic acid monohydrate

toluene

→

white solid

Ausbeute 77.9%

2-(4-Iodophenyl)benzoxazole

Ausbeute 77.9%

Lösungsmittel

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeIn a 300 mL three-neck flask were put
2. 2
   Extraktionfollowed by extraction with ethyl acetate
3. 3
   Waschenwashed with a saturated aqueous sodium hydrogen carbonate solution and saturated brine in that order
4. 4
   workup.ADDITIONAfter that, magnesium sulfate was added to the organic layer
5. 5
   Sonstigeto dry it
6. 6
   Filtrationfiltered through Celite
7. 7
   EinengenThe resulting filtrate was concentrated
8. 8
   Sonstigeto give a solid
9. 9
   SonstigeThis solid was recrystallized with a mixed solvent of ethyl acetate and hexane

Vorschrift

In a 300 mL three-neck flask were put 15 g (44 mmol) of 4-iodo-N-(2-hydroxyphenyl)benzamide and 24 g (0.14 mol) of para-toluenesulfonic acid monohydrate. The atmosphere in the flask was replaced with nitrogen. To this mixture was added 300 mL of toluene. The resulting mixture was stirred under a nitrogen stream at 110° C. for 4 hours. After that, this reaction mixture was added to about 300 mL of water, followed by extraction with ethyl acetate. Then, the organic layer and the extract were combined and washed with a saturated aqueous sodium hydrogen carbonate solution and saturated brine in that order. After that, magnesium sulfate was added to the organic layer to dry it. Next, this mixture was suction filtered through Celite. The resulting filtrate was concentrated to give a solid. This solid was recrystallized with a mixed solvent of ethyl acetate and hexane to give 11 g of a white solid in a yield of 75%.

Quelle