Reacción #4241

Ecuación de reacción

2-(chloromethyl)benzenesulfonamide

butyl isocyanate

→

white solid

Rendimiento 74.8%

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

Rendimiento 74.8%

Disolventes

xylene

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturaheated
2. 2
   Temperaturato reflux for 5.0 hrs
3. 3
   OtroVolatiles were removed under vacuum
4. 4
   workup.ADDITIONthe residue was treated with 0.5N NaOH (200 ml)
5. 5
   Extracciónextracted with ethyl acetate (75 ml)
6. 6
   OtroThe aqueous layer was separated
7. 7
   Temperaturachilled
8. 8
   Extracciónextracted with ethyl acetate
9. 9
   LavadoThe organic layer was washed with brine
10. 10
    Secadodried (MgSO4)
11. 11
    Otroevaporated

Procedimiento

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°.

Fuente