Reacción #67907

Ecuación de reacción

potassium carbonate

3,5-dimethyl-benzoic acid N-tert-butyl-hydrazide

2-fluoro-4-ethyl benzoyl chloride

→

3,5-Dimethyl-benzoic acid N-tert-butyl-N′-(4-ethyl-2-fluoro-benzoyl)-hydrazide

Disolventes

methylene chloride

methylene chloride

water

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONA small stirbar was added
2. 2
   workup.DISSOLUTIONdissolved
3. 3
   OtroThe aqueous phase was removed
4. 4
   Lavadothe organic phase was washed twice with 1 M potassium carbonate solution
5. 5
   OtroThe organic phase was removed
6. 6
   Secadodried over magnesium sulfate
7. 7
   FiltraciónThe organic phase was filtered
8. 8
   Otrothe solvent removed
9. 9
   OtroThe product, 3,5-dimethylbenzoic acid N-tert-butyl-N′-(2-fluoro-4-ethylbenzoyl)-hydrazide, was purified by trituration with 1:1 ether

Procedimiento

0.150 g of 3,5-dimethyl-benzoic acid N-tert-butyl-hydrazide (1 eq, 0.68 mmol) and 0.110 mL (1.2 eq, 0.77 mmol) of 2-fluoro-4-ethyl benzoyl chloride were weighed into a 1 oz. vial. A small stirbar was added followed by 2 mL of methylene chloride. The mixture was stirred until the hydrazone dissolved. The stirring was stopped and 2 mL of a 1 M potassium carbonate (K2CO3) solution was added. The mixture was allowed to stir overnight. At the end of this period, 1 mL of water and 1 mL of methylene chloride were added. The aqueous phase was removed and the organic phase was washed twice with 1 M potassium carbonate solution. The organic phase was removed and dried over magnesium sulfate. The organic phase was filtered thru a pad of basic alumina and the solvent removed. The product, 3,5-dimethylbenzoic acid N-tert-butyl-N′-(2-fluoro-4-ethylbenzoyl)-hydrazide, was purified by trituration with 1:1 ether:hexane. 1H NMR (300 MHz, CDCl3) δ (ppm): 7.7 (m, 2H), 7.6 (t, 1H), 7.0 (m, 3H), 2.6 (q, 2H), 2.3 (s, 3H), 2.1 (s, 6H), 1.5 (s, 9H), 1.1 (t, 3H).

Fuente