반응 #4241

반응 방정식

2-(chloromethyl)benzenesulfonamide

butyl isocyanate

→

white solid

수율 74.8%

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

수율 74.8%

용매

xylene

반응 조건

후처리

1. 1
   온도heated
2. 2
   온도to reflux for 5.0 hrs
3. 3
   기타Volatiles were removed under vacuum
4. 4
   workup.ADDITIONthe residue was treated with 0.5N NaOH (200 ml)
5. 5
   추출extracted with ethyl acetate (75 ml)
6. 6
   기타The aqueous layer was separated
7. 7
   온도chilled
8. 8
   추출extracted with ethyl acetate
9. 9
   세척The organic layer was washed with brine
10. 10
    건조dried (MgSO4)
11. 11
    기타evaporated

실험 절차

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°.

출처