Reaction #5860

Reaction equation

aniline

aniline

toluene

toluenesulfonylisocyanate

→

N-(p-toluenesulfonyl)-N'-phenylurea

Conditions

Workup

1. 1
   OtherA three-necked flask equipped with a dropping funnel
2. 2
   OtherWhile the resultant reaction solution
3. 3
   OtherDuring the stirring, an exothermic reaction
4. 4
   Othera large amount of white solid was precipitated
5. 5
   OtherThe resultant reaction mixture
6. 6
   Temperaturecooled
7. 7
   Filtrationfiltered
8. 8
   OtherWhite crystals were obtained in an amount of 58.0 g

Procedure

A three-necked flask equipped with a dropping funnel, a thermometer, and a reflux condenser was charged with 18.6 g of aniline and the aniline was dissolved in 200 ml of toluene. While the resultant reaction solution was stirred with a magnetic stirrer, 42.0 g of toluenesulfonylisocyanate were added dropwise from the dropping funnel to the reaction solution. During the stirring, an exothermic reaction occurred and a large amount of white solid was precipitated. The resultant reaction mixture was heated at a temperature of 90° C. for one hour, cooled, and then filtered. White crystals were obtained in an amount of 58.0 g. The crystals had a melting point of 166° C.

Source