Diethyl Oxalate → 6-Trifluoromethyloxindole

HRID 1057428Notes

Reaction equation

HRID 1057428 reaction equation
[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

Participants

8

Reactant 4

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

Product 1

HCID 6084876-Trifluoromethyloxindole

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

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

Workup

  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

Sources & evidence

ORD record
ord-7cf27e07f26d4d12827b8af62e66dd4a
Source dataset
uspto-grants-2003_02
Patent number
US06514981B1

Reaction notes

Loading…