Reaktion #94724

Reaktionsgleichung

o-amino-N,N-diethylbenzenesulfonamide

sodium nitrite

sulfur dioxide

→

N,N-diethyl-1,2-benzenedisulfonamide

Lösungsmittel

hydrochloric acid

acetic acid

water

acetic acid

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGThis mixture was stirred at 0° for 15 minutes
2. 2
   FiltrationThe crude sulfonyl chloride was filtered off
3. 3
   Waschenwashed with water
4. 4
   workup.DISSOLUTIONIt was then dissolved in 1 l of ethyl ether
5. 5
   Waschenwashed with water
6. 6
   Trocknendried over magnesium sulfate
7. 7
   workup.ADDITIONTo this ether solution was added 20 ml of liquid anhydrous ammonia at 5°-15°
8. 8
   workup.STIRRINGAfter stirring overnight at room temperature the solid
9. 9
   Filtrationwas filtered off
10. 10
    Waschenwashed with water, ethanol
11. 11
    SonstigeOven drying at 60°

Vorschrift

To a solution of 114 g of o-amino-N,N-diethylbenzenesulfonamide in a mixture of 400 ml of concentrated hydrochloric acid and 100 ml of glacial acetic acid was added a solution of 50 g of sodium nitrite in 130 ml of water at -5° to 0°. The solution was stirred at 0° for 15 minutes then poured into a mixture of 14 g of cuprous chloride and 100 ml of liquid sulfur dioxide in 550 ml of glacial acetic acid at 0°-5°. This mixture was stirred at 0° for 15 minutes then at room temperature for 3 hours before pouring into three liters of ice water. The crude sulfonyl chloride was filtered off and washed with water. It was then dissolved in 1 l of ethyl ether, washed with water and dried over magnesium sulfate. To this ether solution was added 20 ml of liquid anhydrous ammonia at 5°-15°. After stirring overnight at room temperature the solid was filtered off, washed with water, ethanol and then 1-chlorobutane. Oven drying at 60° gave 91.8 g N,N-diethyl-1,2-benzenedisulfonamide, m.p. 156°-9°.

Quelle