Reaktion #46112

Reaktionsgleichung

4,5-Dichloro-2-fluoroaniline

sulphur dioxide

sodium nitrite

ether

→

4,5-dichloro-2-fluorobenzenesulphonamide

Lösungsmittel

acetic acid

hydrochloric acid

methanol

water

acetic acid

water

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONThe resulting mixture is slowly added to suspension A and
2. 2
   SonstigeThe ethereal phase is separated off
3. 3
   Waschenwashed with water (100 mL)
4. 4
   EinengenThe organic phase is concentrated to dryness by distillation under reduced pressure
5. 5
   workup.DISSOLUTIONthe residue is re-dissolved in dioxane (25 mL)
6. 6
   workup.ADDITIONThe solution is poured slowly
7. 7
   workup.STIRRINGwhilst stirring, into a mixture of concentrated ammonia (25 mL) and water (10 mL)
8. 8
   Temperaturcooled on an ice bath
9. 9
   workup.WAITAfter 30 minutes
10. 10
    Sonstigethe solution is evaporated to dryness by distillation under reduced pressure
11. 11
    Sonstigethe residue obtained
12. 12
    workup.ADDITIONThe methanolic solution is treated with absorbent carbon
13. 13
    Filtrationfiltered
14. 14
    Sonstigethe filtrate is evaporated to dryness
15. 15
    SonstigeThe residue is recrystallised from a methanol/water mixture

Vorschrift

In a 500 mL round-bottom flask, a portion of glacial acetic acid (30 mL) is saturated for 30 minutes with a current of gaseous sulphur dioxide. To the resulting solution there is added a solution of cupric chloride (1.5 g) in water (10 mL) (suspension A). 4,5-Dichloro-2-fluoroaniline (5 g) is dissolved in a mixture of glacial acetic acid (30 mL) and concentrated hydrochloric acid (15 mL). The resulting solution is cooled to −5° C. on a bath of ice and salt. A solution of sodium nitrite (2.5 g) in water (10 mL) is then added dropwise with constant stirring. The resulting mixture is slowly added to suspension A and is stirred on an ice bath for 15 minutes. The mixture is then poured into a mixture of water (200 mL) and ether (200 mL). The ethereal phase is separated off and washed with water (100 mL). The organic phase is concentrated to dryness by distillation under reduced pressure and the residue is re-dissolved in dioxane (25 mL). The solution is poured slowly, whilst stirring, into a mixture of concentrated ammonia (25 mL) and water (10 mL) cooled on an ice bath. After 30 minutes, the solution is evaporated to dryness by distillation under reduced pressure and the residue obtained is dissolved in methanol. The methanolic solution is treated with absorbent carbon and filtered and the filtrate is evaporated to dryness. The residue is recrystallised from a methanol/water mixture.

Quelle