Water → 3-(4-Chloro-2-ethyl-6-fluorobenzofuran-7-yl)-1-methyl-6-trifluoromethyluracil

HRID 366315

Reaction equation

HRID 366315 reaction equation
[Cl:1][C:2]1[C:7]2[CH:8]=[C:9]([CH2:11][CH3:12])[O:10][C:6]=2[C:5]([N:13]2[C:18](=[O:19])[CH:17]=[C:16]([C:20]([F:23])([F:22])[F:21])[NH:15][C:14]2=[O:24])=[C:4]([F:25])[CH:3]=1.[C:26](=O)([O-])[O-].[K+].[K+].CI.O>CN(C)C=O>[Cl:1][C:2]1[C:7]2[CH:8]=[C:9]([CH2:11][CH3:12])[O:10][C:6]=2[C:5]([N:13]2[C:18](=[O:19])[CH:17]=[C:16]([C:20]([F:23])([F:21])[F:22])[N:15]([CH3:26])[C:14]2=[O:24])=[C:4]([F:25])[CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 232891763-(4-Chloro-2-ethyl-6-fluorobenzofuran-7-yl)-6-trifluoromethyluracil

Product 1

HCID 154772083-(4-Chloro-2-ethyl-6-fluorobenzofuran-7-yl)-1-methyl-6-trifluoromethyluracilYield 94.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

0.50 g (1.3 mmol) of 3-(4-chloro-2-ethyl-6-fluorobenzofuran-7-yl)-6-trifluoromethyluracil and 0.30 g (2.3 mmol) of potassium carbonate, were suspended in 20 ml of N,N-dimethylformamide, and 0.23 g (1.6 mmol) of methyl iodide was dropwise added thereto under cooling with ice. After stirring at room temperature for 3 hours, the reaction solution was poured into water and extracted with ethyl acetate. The organic layer was washed sequentially with water and a saturated sodium chloride aqueous solution and then dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure. Then, the obtained residue was purified by silica gel column chromatography to obtain 0.48 g (yield: 92%) of the desired product as white crystals. Melting point: 142-143° C.

Workup

  1. temperatureunder cooling with ice
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed sequentially with water
  4. dry with materiala saturated sodium chloride aqueous solution and then dried over anhydrous magnesium sulfate
  5. distillationThe solvent was distilled off under reduced pressure
  6. customThen, the obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-4cc8c6405c384e7bae5f92be5d72802b
Source dataset
uspto-grants-2000_10
Patent number
US06130187

Linked notes

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