تفاعل #4241

معادلة التفاعل

2-(chloromethyl)benzenesulfonamide

butyl isocyanate

→

white solid

المردود 74.8%

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

المردود 74.8%

المذيبات

xylene

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةheated
2. 2
   درجة الحرارةto reflux for 5.0 hrs
3. 3
   أخرىVolatiles were removed under vacuum
4. 4
   workup.ADDITIONthe residue was treated with 0.5N NaOH (200 ml)
5. 5
   استخلاصextracted with ethyl acetate (75 ml)
6. 6
   أخرىThe aqueous layer was separated
7. 7
   درجة الحرارةchilled
8. 8
   استخلاصextracted with ethyl acetate
9. 9
   غسيلThe organic layer was washed with brine
10. 10
    تجفيفdried (MgSO4)
11. 11
    أخرىevaporated

الإجراء التجريبي

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°.

المصدر