Réaction #1340589

Équation de réaction

3-amino-N-[2,6-diethyl-4-(1,2,2,2-tetrafluoro-1-trifluoromethyl-ethyl)phenyl]-4-(1,2,4-triazol-1-yl)benzamide

triethylamine

4-fluorobenzoyl chloride

→

3-(4-fluorobenzoylamino)-N-[2,6-diethyl-4-(1,2,2,2-tetrafluoro-1-trifluoromethylethyl)phenyl]-4-(1,2,4-triazol-1-yl)benzamide

Rendement 82.0%

Solvants

dichloromethane

Conditions de réaction

Traitement

1. 1
   TempératureThe reaction mixture was heated
2. 2
   Températureto reflux for 15 hours
3. 3
   Autrequenched by addition of saturated aqueous sodium hydrogen carbonate (5 ml)
4. 4
   AutreThe phases were separated
5. 5
   Extractionthe aqueous phase was extracted with dichloromethane (2×5 ml)
6. 6
   SéchageThe combined organic phases were dried over sodium sulfate
7. 7
   Concentrationconcentrated
8. 8
   Autrepurification by column chromatography on silica gel (eluent: hexane/ethyl acetate 1:4)
9. 9
   Autreto give Compound No

Mode opératoire

To a solution of 3-amino-N-[2,6-diethyl-4-(1,2,2,2-tetrafluoro-1-trifluoromethyl-ethyl)phenyl]-4-(1,2,4-triazol-1-yl)benzamide (75 mg, 0.15 mmol) (Example I4) in dichloromethane (3 ml) was added triethylamine (63 μl, 0.45 mmol) and 4-fluorobenzoyl chloride (21.3 μl, 0.18 mmol). The reaction mixture was heated to reflux for 15 hours. The reaction mixture was cooled to ambient temperature and quenched by addition of saturated aqueous sodium hydrogen carbonate (5 ml). The phases were separated and the aqueous phase was extracted with dichloromethane (2×5 ml). The combined organic phases were dried over sodium sulfate and concentrated. The residue was purification by column chromatography on silica gel (eluent: hexane/ethyl acetate 1:4) to give Compound No. D2 of Table D (76 mg, 82% yield).

Source