Reaction #927276

Reaction equation

4-fluoro-3-nitro-aniline

benzenesulphonic acid chloride

hydrochloric acid

→

N-{4-fluoro-3-nitro-phenyl}-benzenesulphonamide

Solvents

pyridine

Conditions

Workup

1. 1
   workup.STIRRINGThe mixture is stirred for about 0.5 h at ambient temperature
2. 2
   workup.ADDITIONpoured onto ice water
3. 3
   Extractionis extracted with 150 mL ethyl acetate
4. 4
   Washwashed with water
5. 5
   Otherdried
6. 6
   Concentrationconcentrated by evaporation
7. 7
   workup.DISSOLUTIONThe residue is dissolved in diethylether
8. 8
   workup.ADDITIONdiluted with petroleum ether
9. 9
   Temperaturecooled
10. 10
    OtherThe crystals formed
11. 11
    Filtrationare filtered off
12. 12
    Washwashed with diethylether/petroleum ether
13. 13
    Otherdried

Procedure

4-fluoro-3-nitro-aniline (7.8 g, 50 mmol) is taken up in 50 mL pyridine and cooled to 10° C. The benzenesulphonic acid chloride (7.0 mL, about 55 mmol) is added dropwise with stirring within about 20 min at 10-20° C. The mixture is stirred for about 0.5 h at ambient temperature and poured onto ice water. After acidifying with conc. hydrochloric acid the mixture is extracted with 150 mL ethyl acetate, washed with water, dried and concentrated by evaporation. The residue is dissolved in diethylether, diluted with petroleum ether and cooled. The crystals formed are filtered off, washed with diethylether/petroleum ether and dried.

Source