Diethyl Oxalate → 6-Trifluoromethyloxindole

HRID 1057428

Reaktionsgleichung

Reaktionsgleichung von HRID 1057428
[H-].[Na+].C(OC(=O)C([O:9][CH2:10][CH3:11])=O)C.[N+:13]([C:16]1[CH:21]=[C:20]([C:22]([F:25])([F:24])[F:23])[CH:19]=[CH:18][C:17]=1C)([O-])=O.[Cl-].[NH4+]>CCCCCC.C(OCC)(=O)C.CS(C)=O>[F:23][C:22]([F:24])([F:25])[C:20]1[CH:21]=[C:16]2[C:17]([CH2:11][C:10](=[O:9])[NH:13]2)=[CH:18][CH:19]=1

Komponenten

8

Edukt 4

HCID 7268Diethyl OxalateHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 14728854-Methyl-3-nitrobenzotrifluoride

Produkt 1

HCID 6084876-Trifluoromethyloxindole

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 679Dimethyl SulfoxideLösungsmittelHCID 8058HexaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

Dimethylsulfoxide (330 mL) was added to 7.9 g of sodium hydride followed by, dropwise, 43.6 g of diethyloxalate. The mixture was heated to 100° C. for 1 hour and cooled to room temperature. 2-Nitro-4-trifluromethyltoluene (31.3 g) was added, the reaction stirred for 30 minutes at room temperature and then heated to 100° C. for 1 hour. The reaction was cooled and poured into a mixture of saturated aqueous ammonium chloride, ethyl acetate and hexane. The organic layer was washed with saturated ammonium chloride, water and brine, dried, and concentrated to give dimethyl

Aufarbeitung

  1. temperaturecooled to room temperature
  2. temperatureheated to 100° C. for 1 hour
  3. temperatureThe reaction was cooled
  4. washThe organic layer was washed with saturated ammonium chloride, water and brine
  5. customdried
  6. concentrationconcentrated
  7. customto give dimethyl

Quellen und Nachweise

ORD-Eintrag
ord-7cf27e07f26d4d12827b8af62e66dd4a
Quelldatensatz
uspto-grants-2003_02
Patentnummer
US06514981B1

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