Reaktion #2374035

Reaktionsgleichung

Dimethylformamide

thionyl chloride

3,4-dihydro-2-trichloromethyl-2H-benzo[e]-[1,3]-oxazin-4-one

→

3-formyl-3,4-dihydro-2-trichloromethyl-2H-benzo[e]-[1,3]-oxazin-4-one

Lösungsmittel

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGstirred for 1 hour
2. 2
   Filtrationfiltered
3. 3
   workup.DISSOLUTIONThe solid product was dissolved in toluene
4. 4
   Sonstigepurified by column chromatography on "Kieselgel"-60 (trade mark)
5. 5
   Wascheneluting with a mixture of 5% by volume of ethyl acetate in toluene
6. 6
   SonstigeThe solvent was evaporated
7. 7
   Sonstigethe product was crystallised from petroleum ether (b.p. 60°-80° C.)

Vorschrift

Dimethylformamide (20 ml.) and thionyl chloride (5 ml.) were stirred together, 3,4-dihydro-2-trichloromethyl-2H-benzo[e]-[1,3]-oxazin-4-one (2.0 g.) was added in small portions over 15 minutes, and the mixture was stirred at ambient temperature for 48 hours. The reaction mixture was added to water (100 ml.), stirred for 1 hour and filtered. The solid product was dissolved in toluene, and purified by column chromatography on "Kieselgel"-60 (trade mark), eluting with a mixture of 5% by volume of ethyl acetate in toluene. The solvent was evaporated, and the product was crystallised from petroleum ether (b.p. 60°-80° C.) to give 3-formyl-3,4-dihydro-2-trichloromethyl-2H-benzo[e]-[1,3]-oxazin-4-one, m.p. 114° C.

Quelle