Reaction #4241

Reaction equation

2-(chloromethyl)benzenesulfonamide

butyl isocyanate

→

white solid

Yield 74.8%

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

Yield 74.8%

Solvents

xylene

Conditions

Workup

1. 1
   Temperatureheated
2. 2
   Temperatureto reflux for 5.0 hrs
3. 3
   OtherVolatiles were removed under vacuum
4. 4
   workup.ADDITIONthe residue was treated with 0.5N NaOH (200 ml)
5. 5
   Extractionextracted with ethyl acetate (75 ml)
6. 6
   OtherThe aqueous layer was separated
7. 7
   Temperaturechilled
8. 8
   Extractionextracted with ethyl acetate
9. 9
   WashThe organic layer was washed with brine
10. 10
    Dryingdried (MgSO4)
11. 11
    Otherevaporated

Procedure

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°.

Source