Reaction #1340589

Reaction equation

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

Yield 82.0%

Solvents

dichloromethane

Conditions

Workup

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

Procedure

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