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To a solution of 4.0 g (0.03 mole) of oxindole in 125 ml dry glyme there is added 1.4 g (0.03 mole) of sodium hydride (50% oil dispersion) and the mixture is stirred at room temperature for 3 hours. Then 3.6 g (0.3 mole) of 2-chloroethyl isothiocyanate in 5 ml of dry glyme is added and the mixture is refluxed overnight. After evaporation of the solvent in vacuo, the residue is chromatographed on an Alumina Act. IV column. Elution with ethyl ether yields the product which is crystallized from ethyl ether to yield 0.6 g, m.p. 97°-99°.

1. temperaturethe mixture is refluxed overnight
2. customAfter evaporation of the solvent in vacuo
3. customthe residue is chromatographed on an Alumina Act
4. washElution with ethyl ether
5. customyields the product which
6. customis crystallized from ethyl ether
7. customto yield 0.6 g, m.p. 97°-99°