Reaktion #54247
ord-f96e9ff5ba8147c991cb80b144fa53c2
Reaktionsgleichung
p-chloroaniline
t-butyl hypochlorite
triethylamine
2-ethylmercaptobutyrolactone
→
5-chloro-3-(2-hydroxyethyl)-3-ethylmercapto-2-oxindole
Reagenzien
Keine
Reaktionsbedingungen
Detaillierte Bedingungen
See reaction.notes.procedure_details.
Aufarbeitung
- 1workup.WAITAfter ten minutes
- 2Filtrationthe precipitate filtered off
Vorschrift
To the stirred solution of 5.6 g p-chloroaniline in 150 ml of methylene chloride is added dropwise 4.7 ml of t-butyl hypochlorite in 20 ml of methylene chloride at -65°. After ten minutes, the solution of 5.75 g of 2-ethylmercaptobutyrolactone in 20 ml of methylene chloride is added dropwise and the temperature held at -65° for two hours. Then the solution of 6.1 ml of triethylamine in 20 ml of methylene chloride is added dropwise and the mixture is allowed to warm up to room temperature. 50 ml of water are added with stirring and the precipitate filtered off, to yield the 5-chloro-3-(2-hydroxyethyl)-3-ethylmercapto-2-oxindole melting at 132°-135°.