Réaction #65071

Équation de réaction

4-fluoro-3-nitroaniline

ethanesulfonyl chloride

→

objective product

Rendement 93.0%

N-(4-fluoro-3-nitrophenyl)ethanesulfonamide

Rendement 93.0%

Solvants

pyridine

Conditions de réaction

Traitement

1. 1
   workup.WAITthe reaction was continued for one night
2. 2
   workup.DISTILLATIONAfter the pyridine was distilled off
3. 3
   workup.DISSOLUTIONthe thus-obtained product was dissolved in ethyl acetate
4. 4
   Lavagewashed with diluted hydrochloric acid twice
5. 5
   SéchageThe solution was dried over anhydrous sodium sulfate
6. 6
   workup.DISTILLATIONthe ethyl acetate was distilled off
7. 7
   Autreto obtain the crude product (crystals)
8. 8
   LavageThe crude product was washed with diisopropyl ether

Mode opératoire

20.2 g (0.129 mol) of 4-fluoro-3-nitroaniline was dissolved in 120 ml of pyridine, and 17.8 g (0.136 mol) of ethanesulfonyl chloride was added dropwise to the solution at a temperature of not higher than 5° C. Thereafter the temperature was raised to room temperature and the reaction was continued for one night. After the pyridine was distilled off, the thus-obtained product was dissolved in ethyl acetate and washed with diluted hydrochloric acid twice, then with water, and with saturated saline solution. The solution was dried over anhydrous sodium sulfate, and the ethyl acetate was distilled off to obtain the crude product (crystals). The crude product was washed with diisopropyl ether, thereby obtaining 29.7 g of the objective product (yield: 93%) in the form of brown crystals. Melting point: 133° to 136° C.

Source