Reaktion #4241

Reaktionsgleichung

2-(chloromethyl)benzenesulfonamide

butyl isocyanate

→

white solid

Ausbeute 74.8%

2-(Chloromethyl)-N-(butylaminocarbonyl)benzenesulfonamide

Ausbeute 74.8%

Lösungsmittel

xylene

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturheated
2. 2
   Temperaturto reflux for 5.0 hrs
3. 3
   SonstigeVolatiles were removed under vacuum
4. 4
   workup.ADDITIONthe residue was treated with 0.5N NaOH (200 ml)
5. 5
   Extraktionextracted with ethyl acetate (75 ml)
6. 6
   SonstigeThe aqueous layer was separated
7. 7
   Temperaturchilled
8. 8
   Extraktionextracted with ethyl acetate
9. 9
   WaschenThe organic layer was washed with brine
10. 10
    Trocknendried (MgSO4)
11. 11
    Sonstigeevaporated

Vorschrift

A mixture of 2-(chloromethyl)benzenesulfonamide (13.2 g, 64 mmol) and butyl isocyanate (7.0 g, 71 mmol) in xylene (80 ml) was contacted with diazabicyclo[2.2.2]octane (0.25 g) and heated to reflux for 5.0 hrs. Volatiles were removed under vacuum and the residue was treated with 0.5N NaOH (200 ml) and extracted with ethyl acetate (75 ml). The aqueous layer was separated, chilled, acidified (pH 4) with hydrochloric acid, and extracted with ethyl acetate. The organic layer was washed with brine, dried (MgSO4), and evaporated to give 14.6 g of white solid. A sample was recrystallized from toluene to give m.p. 104°-106°.

Quelle