Reaktion #2298358

Reaktionsgleichung

Potassium hydroxide

2-[(3-trifluoromethylphenyl)amino]-benzoic acid, hydrazide

carbon disulfide

→

product

Ausbeute 69.0%

5-[2-[[3-(Trifluoromethyl)phenyl]amino]phenyl]-1,3,4-oxadiazol-2(3H)-thione

Ausbeute 69.0%

Lösungsmittel

methanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe mixture is heated
2. 2
   Temperaturat reflux overnight
3. 3
   EinengenThe solution is concentrated in vacuo
4. 4
   workup.DISSOLUTIONthe residue dissolved in water
5. 5
   Extraktionthe resulting solids extracted into a 1:1 mixture of ether and ethyl acetate
6. 6
   WaschenThe organic layer is washed with brine
7. 7
   Trocknendried over magnesium sulfate
8. 8
   Filtrationfiltered
9. 9
   Einengenconcentrated in vacuo
10. 10
    SonstigeThe residue is chromatographed
11. 11
    Wascheneluting with hexane:ethyl acetate (1:1)
12. 12
    Sonstigeproviding a white solid
13. 13
    SonstigeDrying in vacuo at 65° C. overnight

Vorschrift

Potassium hydroxide (123.0 mg, 1.87 mmol) is added to a 020 C. solution of 2-[(3-trifluoromethylphenyl)amino]-benzoic acid, hydrazide (515.8 mg, 1.75 mmol) and carbon disulfide (250 μl, 3.96 mmol) in 15 ml of methanol. The mixture is heated at reflux overnight. The solution is concentrated in vacuo and the residue dissolved in water. The resulting aqueous solution is acidified with 1N hydrochloric acid and the resulting solids extracted into a 1:1 mixture of ether and ethyl acetate. The organic layer is washed with brine, dried over magnesium sulfate, filtered and concentrated in vacuo. The residue is chromatographed, eluting with hexane:ethyl acetate (1:1), providing a white solid. Drying in vacuo at 65° C. overnight gives 406.4 mg (69%) of product, mp 211°-213° C.

Quelle