Реакция #49909

Уравнение реакции

N'-t-butyl-N-benzoyl-N'-(3,5-dimethylbenzoyl)hydrazine

sodium hydride

propargyl bromide

→

N-(2-propynyl)-N'-(3,5-dimethylbenzoyl)hydrazine

Выход 70.0%

Растворители

dimethylformamide

ethyl acetate

Условия реакции

Обработка

1. 1
   Промывкаwashed with water (5×20 ml)
2. 2
   СушкаThe organic layer was then dried over magnesium sulfate
3. 3
   Другоеthe solvent removed under vacuum

Методика

To a stirred suspension of N'-t-butyl-N-benzoyl-N'-(3,5-dimethylbenzoyl)hydrazine (1.5 g) in dimethylformamide (DMF) (20 ml) was added sodium hydride (200 mg of 60% oil dispersion) portionwise. After 15 min., propargyl bromide (0.6 g) was added to the reaction mixture dropwise and the reaction stirred for 1 hour. The reaction mixture was diluted with ethyl acetate (50 ml) and washed with water (5×20 ml). The organic layer was then dried over magnesium sulfate and the solvent removed under vacuum to afford N-(2-propynyl)-N'-(3,5-dimethylbenzoyl)hydrazine as a yellow amorphous solid. The product, N-(2-propynyl)-N'-t-butyl-N-benzoyl-N'-(3,5-dimethylbenzoyl)hydrazine, was purified by column chromatography on silica gel (solvent system: methylene chloride) to afford a 70% yield as a white solid.

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