Potassium Acetate → HCID 53794938, compound

HRID 366335Notes

Reaction equation

HRID 366335 reaction equation
[C:1]([C:4]1[C:8]2[C:9]([Cl:27])=[CH:10][C:11]([F:26])=[C:12]([N:13]3[C:18](=[O:19])[CH:17]=[C:16]([C:20]([F:23])([F:22])[F:21])[N:15]([CH3:24])[C:14]3=[O:25])[C:7]=2[O:6][C:5]=1[CH3:28])(=O)[CH3:2].C([O-])(=O)C.[K+].Cl.[CH3:35][O:36][NH2:37]>CO>[Cl:27][C:9]1[C:8]2[C:4]([C:1](=[N:37][O:36][CH3:35])[CH3:2])=[C:5]([CH3:28])[O:6][C:7]=2[C:12]([N:13]2[C:18](=[O:19])[CH:17]=[C:16]([C:20]([F:23])([F:21])[F:22])[N:15]([CH3:24])[C:14]2=[O:25])=[C:11]([F:26])[CH:10]=1

Participants

5

Reactant 3

HCID 517044Potassium AcetateHCID 521874O-Methylhydroxylamine hydrochlorideHCID 15477254HCID 15477254, compound

Product 1

HCID 53794938HCID 53794938, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

50 ml of methanol was added to 0.4 g (1 mmol) of 3-(3-acetyl-4-chloro-6-fluoro-2-methylbenzofuran-7-yl)-1-methyl-6-trifluoromethyluracil, 0.5 g (5 mmol) of potassium acetate and 0.5 g (6 mmol) of methoxyamine hydrochloride, followed by stirring at room temperature for 12 hours and further for 8 hours under heating and refluxing. After completion of the reaction, methanol was distilled off under reduced pressure, ethyl acetate was added to the obtained residue, and the mixture was washed sequentially with water and a saturated sodium chloride aqueous solution. The organic layer was dried over anhydrous sodium sulfate. Then, the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography to obtain 0.4 g (yield: 100%) of the desired product as pale yellow crystals. Melting point: 65-67° C., 1H-NMR (solvent: CDCl3): 1.54 (1H,s), 2.21(3H,s), 2.35(3H,s), 3.59(3H,s), 3.91(3H,s), 6.41(1H,s), 7.16(1H,d)ppm

Workup

  1. temperatureunder heating
  2. temperaturerefluxing
  3. distillationwas distilled off under reduced pressure, ethyl acetate
  4. additionwas added to the obtained residue
  5. washthe mixture was washed sequentially with water
  6. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  7. distillationThen, the solvent was distilled off under reduced pressure
  8. customThe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-fc267559d4414ef1b72cd4fb87a1df0b
Source dataset
uspto-grants-2000_10
Patent number
US06130187

Reaction notes

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