Ethanol → HCID 53881481, compound

HRID 440665Notes

Reaction equation

HRID 440665 reaction equation
[Cl:1][C:2]1[C:7]2[C:8](=O)[C:9]([CH3:12])([CH3:11])[O:10][C:6]=2[C:5]([N:14]2[C:19](=[O:20])[CH:18]=[C:17]([C:21]([F:24])([F:23])[F:22])[N:16]([CH3:25])[C:15]2=[O:26])=[C:4]([Cl:27])[CH:3]=1.[CH3:28][O:29][NH3+:30].[Cl-].C(O)C.N1C=CC=CC=1>C(OCC)(=O)C>[Cl:1][C:2]1[C:7]2[C:8](=[N:30][O:29][CH3:28])[C:9]([CH3:11])([CH3:12])[O:10][C:6]=2[C:5]([N:14]2[C:19](=[O:20])[CH:18]=[C:17]([C:21]([F:24])([F:23])[F:22])[N:16]([CH3:25])[C:15]2=[O:26])=[C:4]([Cl:27])[CH:3]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 1049PyridineHCID 11639O-methylhydroxylammonium chlorideHCID 22404772HCID 22404772, compound

Product 1

HCID 53881481HCID 53881481, compoundYield 21.2%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

In a flask were placed 3.20 g (0.0076 mole) of 3-(4,6-dichloro-2,3-dihydro-2,2-dimethylbenzofuran-3-on-7-yl)-1-methyl-6-trifluoromethyluracil, 1,20 g (0.0144 mole) of 0-methylhydroxylamine hydrochloride, 4 mL of ethanol, and 4 mL of pyridine. This mixture was heated at reflux for five hours and then was evaporated under reduced pressure, leaving a residue. The residue was dissolved in ethyl acetate, and this solution was washed with water. The aqueous washings were then extracted twice with ethyl acetate, and these extracts were combined with the ethyl acetate solution of the product. The combined extracts and solution was dried over anhydrous magnesium sulfate, filtered, and the solvent was evaporated from the filtrate under reduced pressure, leaving a light reddish, viscous oil as a residue. This oil was passed through a column of silica gel, eluting with methylene chloride. Product-containing fractions were combined, and the solvent evaporated under reduced pressure, leaving 0.73 g of 3-(4,6-dichloro-2,3-dihydro-2,2-dimethyl-3-methoxyiminobenzofuran-7-yl)-1-methyl-6-trifluoromethyluracil (Compound 26) as an off-white, fluffy solid, m.p. 145°-149° C. The NMR and IR spectra were consistent with the proposed structure.

Workup

  1. customIn a flask were placed
  2. temperatureThis mixture was heated
  3. temperatureat reflux for five hours
  4. customwas evaporated under reduced pressure
  5. customleaving a residue
  6. washthis solution was washed with water
  7. extractionThe aqueous washings were then extracted twice with ethyl acetate
  8. dry with materialThe combined extracts and solution was dried over anhydrous magnesium sulfate
  9. filtrationfiltered
  10. customthe solvent was evaporated from the filtrate under reduced pressure
  11. customleaving a light reddish, viscous oil as a residue
  12. washeluting with methylene chloride
  13. customthe solvent evaporated under reduced pressure

Sources & evidence

ORD record
ord-619b96f40c7a44799fe9802a0a232d6c
Source dataset
uspto-grants-1996_05
Patent number
US05521147

Reaction notes

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