Реакция #87724

Уравнение реакции

trimethyl aluminium

methyl 4-[3-(2-chloro-6-fluorophenyl)-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl]benzoate

3-trifloromethyl aniline

→

desired product

Выход 30.0%

4-(3-(2-Chloro-6-fluorophenyl)-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl)-N-(3-(trifluoromethyl)phenyl)benzamide

Выход 30.0%

Растворители

toluene

Условия реакции

Обработка

1. 1
   ТемператураThe reaction mixture was refluxed for 1 h
2. 2
   ДругоеThe reaction mass was quenched in water
3. 3
   Экстракцияextracted in DCM
4. 4
   СушкаThe organic layer was dried over anhydrous sodium sulphate
5. 5
   Концентрированиеconcentrated
6. 6
   Другоеto afford crude product, which
7. 7
   Другоеpurified

Методика

To a solution of methyl 4-[3-(2-chloro-6-fluorophenyl)-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl]benzoate (step-2 of Intermediate-9, 0.100 g, 0.28 mmol) in dry toluene was added 3-trifloromethyl aniline (0.070 g, 0.43 mmol) followed by addition of trimethyl aluminium (2M solution in toluene) (0.5 mL). The reaction mixture was refluxed for 1 h. The reaction mass was quenched in water and acidified with dilute HCl and extracted in DCM. The organic layer was dried over anhydrous sodium sulphate and concentrated to afford crude product, which was column purified to afford 0.040 g of desired product. 1H NMR (DMSO-d6): δ 7.45-7.54 (m, 2H), 7.59 (m, 2H), 7.72 (q, J=6.3 Hz, 1H), 8.05-8.12 (m, 5H), 8.25 (s, 1H), 10.58 (br s, 1H), 12.77 (br s, 1H); MS (m/z): 477.08 [M+H]+.

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