Reaction #4577

Reaction equation

methyl 5-chlorooxindole-3-carboxylate

phenylisocyanate

→

Methyl 1-N-(phenyl)carbamoyl-5-chlorooxindole-3-carboxylate

Solvents

toluene

—

petroleum ether

Conditions

Workup

1. 1
   Temperatureheated
2. 2
   Temperatureto reflux overnight
3. 3
   TemperatureThe reaction mixture was cooled
4. 4
   Otherto give
5. 5
   Filtrationafter filtration
6. 6
   Otherdrying

Procedure

To 6.0 g. (0.027 mole) of methyl 5-chlorooxindole-3-carboxylate in 200 ml. of toluene was added 5.25 ml. (0.048 mole) of phenylisocyanate and the resulting reaction mixture heated to reflux overnight. The reaction mixture was cooled and diluted with petroleum ether to give, after filtration and drying, 2.0 g. of the desired product.

Source