تفاعل #63147

معادلة التفاعل

iodobenzene

ammonium hydroxide

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

n-butyllithium

→

material

المردود 68.4%

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

المردود 68.4%

المذيبات

ethyl acetate

—

hexanes

tetrahydrofuran

Acetic acid

ظروف التفاعل

المعالجة

1. 1
   أخرىthen recooled to -20°
2. 2
   workup.WAITAfter 10 minutes at -15°
3. 3
   درجة الحرارةthe mixture was then heated
4. 4
   درجة الحرارةto reflux overnight
5. 5
   درجة الحرارةafter cooling the mixture to 15°
6. 6
   workup.STIRRINGthe mixture was stirred vigorously in the presence of air
7. 7
   أخرىremoval of the copper salts
8. 8
   أخرىThe aqueous phase was separated
9. 9
   استخلاصextracted with more ethyl acetate
10. 10
    غسيلthe combined organic extracts were washed successively with concentrated ammonium hydroxide, water and brine
11. 11
    تجفيفdried (MgSO4)
12. 12
    أخرىevaporated to an oil
13. 13
    أخرىThe product crystallized from ether/hexanes

الإجراء التجريبي

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°.

المصدر