Реакция #10832

Уравнение реакции

4-acetyl-benzenesulfonamide

5-(4-isobutyl-4H-[1,2,4]triazol-3-yl)-2,4-dimethoxy-benzaldehyde

lithium methoxide

→

title compound

4-{3E-[5-(4-Isobutyl-4H-[1,2,4]triazol-3-yl)-2,4-dimethoxy-phenyl]-acryloyl}-benzenesulfonamide

Растворители

N,N-dimethylformamide

Условия реакции

Обработка

1. 1
   ДругоеThe reaction was quenched with water
2. 2
   ПромывкаThe aqueous solution was washed ethyl acetate
3. 3
   Экстракцияextracted with dichloromethane, isopropyl alcohol (33%, v/v, in dichloromethane)
4. 4
   ПромывкаThe combined dichloromethane and isopropyl alcohol was washed with brine
5. 5
   Сушкаdried over sodium sulfate
6. 6
   Концентрированиеconcentrated
7. 7
   workup.STIRRINGThe crude product was then stirred in ethanol (50%, v/v, in acetone)

Методика

To a solution of 4-acetyl-benzenesulfonamide (Ex-26A, 0.12 g, 0.62 mmol) and 5-(4-isobutyl-4H-[1,2,4]triazol-3-yl)-2,4-dimethoxy-benzaldehyde (Ex-109E, 0.18 g, 0.62 mmol) in N,N-dimethylformamide (9 mL) was added lithium methoxide (1.0M in methanol, 2.4 mL, 2.4 mmol). The solution was allowed to stir overnight. The reaction was quenched with water. The aqueous solution was washed ethyl acetate, acidified to pH 5, extracted with dichloromethane, isopropyl alcohol (33%, v/v, in dichloromethane). The combined dichloromethane and isopropyl alcohol was washed with brine, dried over sodium sulfate and concentrated. The crude product was then stirred in ethanol (50%, v/v, in acetone) to give the title compound as a light yellow solid: m.p.>240° C. 1H NMR (DMSO-d6) δ 8.60 (s, 1H), 8.26 (d, J=8.1 Hz, 2H), 8.06 (d, J=15.3 Hz, 1H), 8.07 (s, 1H), 7.91 (d, J=8.1 Hz, 2H), 7.84 (d, J=15.3 Hz, 1H), 7.50 (s, 1H), 6.84 (s, 1H), 4.01 (s, 3H), 3.87 (s, 3H), 3.61 (d, J=7.3 Hz, 2H), 1.81–1.74 (m, 1H), 0.67 (d, J=16.7 Hz, 6H). MS m/z=471 ([M+H]+, 100%).

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