Reaction #4582

Reaction equation

phosgene

2-(1-methoxycarbonylethoxy)-benzenesulfonamide

n-butylisocyanate

phosgene

→

2-(1-methoxycarbonylethoxy)benzenesulfonyl isocyanate

Yield 125.5%

Solvents

xylene

Conditions

Workup

1. 1
   Temperatureis refluxed for 30 minutes
2. 2
   Temperaturethe solution is then cooled
3. 3
   Concentrationconcentrated in vacuo

Procedure

A mixture of 12.9 g of 2-(1-methoxycarbonylethoxy)-benzenesulfonamide, 4.9 g of n-butylisocyanate and 0.1 g of diazabicyclooctane and 130 ml of xylene is refluxed for 30 minutes. Then 10 g of phosgene are passed into the solution at the same temperature over 90 minutes. Excess phosgene is expelled with nitrogen and the solution is then cooled and concentrated in vacuo, affording 17.7 g of 2-(1-methoxycarbonylethoxy)benzenesulfonyl isocyanate in the form of a brownish oil which can be further used without purification.

Source