Reaktion #1138434

Reaktionsgleichung

4-Methyl-3-nitrobenzoic acid

HATU

DIPEA

3-(trifluoromethyl)aniline

→

title compound

Ausbeute 74.0%

4-methyl-3-nitro-N-(3-(trifluoromethyl)phenyl)benzamide

Ausbeute 74.0%

Lösungsmittel

dimethyl formamide

ethyl acetate

Reaktionsbedingungen

Aufarbeitung

1. 1
   Waschenwashed with a saturated aqueous sodium bicarbonate solution and saline
2. 2
   SonstigeThe organic layer thus obtained
3. 3
   Trocknenwas dried over anhydrous sodium sulfate
4. 4
   Filtrationfiltered
5. 5
   Einengenconcentrated under reduced pressure
6. 6
   workup.ADDITIONThe concentrated solid was added with ethyl acetate
7. 7
   workup.STIRRINGstirred for 2 hours or more
8. 8
   FiltrationThe resulting solid was filtered under reduced pressure
9. 9
   Waschenwashed with ethyl acetate and methanol
10. 10
    SonstigeThe filtered solid was dried
11. 11
    Temperaturwith warm wind in an oven (40° C.) for 3 hours or more

Vorschrift

4-Methyl-3-nitrobenzoic acid (14.6 g, 81.0 mmol) was stirred in a solvent of dimethyl formamide (40 mL). The reaction solution was added with HATU (47.2 g, 124 mmol), DIPEA (32.5 mL, 186 mmol) and 3-(trifluoromethyl)aniline (7.72 mL, 62.1 mmol), followed by stirring for about 12 hours at room temperature. The reaction mixture was diluted with ethyl acetate, and washed with a saturated aqueous sodium bicarbonate solution and saline. The organic layer thus obtained was dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The concentrated solid was added with ethyl acetate, and stirred for 2 hours or more. The resulting solid was filtered under reduced pressure, and washed with ethyl acetate and methanol. The filtered solid was dried with warm wind in an oven (40° C.) for 3 hours or more to obtain the title compound (14.9 g, 74%).

Quelle