反応 #63147

反応方程式

iodobenzene

ammonium hydroxide

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

n-butyllithium

→

material

収率 68.4%

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

収率 68.4%

溶媒

ethyl acetate

—

hexanes

tetrahydrofuran

Acetic acid

反応条件

後処理

1. 1
   その他then recooled to -20°
2. 2
   workup.WAITAfter 10 minutes at -15°
3. 3
   温度the mixture was then heated
4. 4
   温度to reflux overnight
5. 5
   温度after cooling the mixture to 15°
6. 6
   workup.STIRRINGthe mixture was stirred vigorously in the presence of air
7. 7
   その他removal of the copper salts
8. 8
   その他The aqueous phase was separated
9. 9
   抽出extracted with more ethyl acetate
10. 10
    洗浄the combined organic extracts were washed successively with concentrated ammonium hydroxide, water and brine
11. 11
    乾燥dried (MgSO4)
12. 12
    その他evaporated to an oil
13. 13
    その他The product crystallized from ether/hexanes

実験手順

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°.

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