반응 #63147

반응 방정식

iodobenzene

ammonium hydroxide

N-(1,1-dimethylethyl)-2-(methylthio)benzenesulfonamide

n-butyllithium

→

material

수율 68.4%

N-(1,1-Dimethylethyl)-2-(methylthio)-6-phenylbenzenesulfonamide

수율 68.4%

용매

ethyl acetate

—

hexanes

tetrahydrofuran

Acetic acid

반응 조건

후처리

1. 1
   기타then recooled to -20°
2. 2
   workup.WAITAfter 10 minutes at -15°
3. 3
   온도the mixture was then heated
4. 4
   온도to reflux overnight
5. 5
   온도after cooling the mixture to 15°
6. 6
   workup.STIRRINGthe mixture was stirred vigorously in the presence of air
7. 7
   기타removal of the copper salts
8. 8
   기타The aqueous phase was separated
9. 9
   추출extracted with more ethyl acetate
10. 10
    세척the combined organic extracts were washed successively with concentrated ammonium hydroxide, water and brine
11. 11
    건조dried (MgSO4)
12. 12
    기타evaporated to an oil
13. 13
    기타The product crystallized from ether/hexanes

실험 절차

A solution of 11.3 g (0.0436 mol) N-(1,1-dimethylethyl)-2-(methylthio)benzenesulfonamide in 300 ml tetrahydrofuran (THF) was treated with 60.5 ml (0.096 mol) 2M n-butyllithium in hexanes at -30° under a nitrogen atmosphere. The mixture was stirred for 1 hour at ambient temperature then recooled to -20° and treated with 8.3 g (0.0436 mol) of cuprous iodide (anhydrous). After 10 minutes at -15°, 4.9 ml (0.0438 mol) iodobenzene was added and the mixture was then heated to reflux overnight. Acetic acid (10 ml) was added after cooling the mixture to 15°, then 200 ml concentrated ammonium hydroxide plus 200 ml ethyl acetate was introduced and the mixture was stirred vigorously in the presence of air to facilitate removal of the copper salts. The aqueous phase was separated, extracted with more ethyl acetate and the combined organic extracts were washed successively with concentrated ammonium hydroxide, water and brine, then dried (MgSO4) and evaporated to an oil. The product crystallized from ether/hexanes to afford 10 g of material, m.p. 162°-165°.

출처