Citric Acid → HCID 23289189, compound

HRID 366341Notes

Reaction equation

HRID 366341 reaction equation
O1CCOC[CH2:2]1.[Cl:7][C:8]1[C:13]2[CH:14]=[C:15]([CH:17]=O)[O:16][C:12]=2[C:11]([N:19]2[C:24](=[O:25])[CH:23]=[C:22]([C:26]([F:29])([F:28])[F:27])[N:21]([CH3:30])[C:20]2=[O:31])=[C:10]([F:32])[CH:9]=1.C(=O)([O-])[O-].[K+].[K+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O>[Cl:7][C:8]1[C:13]2[CH:14]=[C:15]([CH:17]=[CH2:2])[O:16][C:12]=2[C:11]([N:19]2[C:24](=[O:25])[CH:23]=[C:22]([C:26]([F:28])([F:27])[F:29])[N:21]([CH3:30])[C:20]2=[O:31])=[C:10]([F:32])[CH:9]=1

Participants

7

Reactant 4

HCID 311Citric AcidHCID 11430Potassium CarbonateHCID 312751,4-DioxaneHCID 15477226HCID 15477226, compound

Product 1

HCID 23289189HCID 23289189, compoundYield 51%

Reagents, catalysts & solvents 2

HCID 74505Methyltriphenyliphosphonium bromideCatalystHCID 962WaterSolvent2×

Procedure

50 ml of dioxane and 0.5 ml of water were added to 1.0 g (2.6 mmol) of 3-(4-chloro-6-fluoro-2-formylbenzofuran-7-yl)-1-methyl-6-trifluoromethyluracil, 0.94 g (2.6 mmol) of methyltriphenylphosphonium bromide and 0.43 g (3.1 mmol) of potassium carbonate, followed by stirring for 2 hours under heating and refluxing. After completion of the reaction, the reaction solution was poured into water and adjusted to pH 3 with an aqueous citric acid solution and then, 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 0.51 g (yield: 51%) of the desired product as yellow crystals. Melting point: 108-109° C.

Workup

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

Sources & evidence

ORD record
ord-0cc31ac2f3e14c84be339130c397672b
Source dataset
uspto-grants-2000_10
Patent number
US06130187

Reaction notes

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