Hydrochloric Acid → HCID 15477231, compound

HRID 366320Notes

Reaction equation

HRID 366320 reaction equation
[Cl:1][C:2]1[C:7]2[CH:8]=[CH:9][O:10][C:6]=2[C:5]([N:11]2[C:16](=[O:17])[CH:15]=[C:14]([C:18]([F:21])([F:20])[F:19])[N:13]([CH3:22])[C:12]2=[O:23])=[C:4]([F:24])[CH:3]=1.[Cl-].[Al+3].[Cl-].[Cl-].[C:29](Cl)(=[O:32])[CH2:30][CH3:31].Cl>[N+](C)([O-])=O>[Cl:1][C:2]1[C:7]2[CH:8]=[C:9]([C:29](=[O:32])[CH2:30][CH3:31])[O:10][C:6]=2[C:5]([N:11]2[C:16](=[O:17])[CH:15]=[C:14]([C:18]([F:21])([F:20])[F:19])[N:13]([CH3:22])[C:12]2=[O:23])=[C:4]([F:24])[CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 62324Propionyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 15477206HCID 15477206, compound

Product 1

HCID 15477231HCID 15477231, compoundYield 56.3%

Reagents, catalysts & solvents 1

HCID 6375NitromethaneSolvent

Procedure

1.3 g (1.4 mmol) of 3-(4-chloro-6-fluorobenzofuran-7-yl)-1-methyl-6-trifluoromethyluracil and 1.9 g (1.4 mmol) of aluminum chloride, were dissolved in 20 ml of nitromethane, and 0.5 g (1.4 mmol) of propionyl chloride was dropwise added thereto under cooling with ice. After completion of the dropwise addition, the mixture was stirred at room temperature for 12 hours. After completion of the reaction, the reaction solution was poured into a mixture of dilute hydrochloric acid and ice and extracted with ethyl acetate. The organic layer was washed sequentially with water and a saturated s odium chloride aqueous solution and then dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure. Then, the obtained residue was purified by silica gel column chromatography to obtain 0.33 g (yield: 56%) of the desired product as a yellow glassy substance. Refractive index: unmeasurable, 1H-NMR (solvent, CDCl3): 1.20(3H,m), 2.91(2H,q), 3.56(3H,s), 6.38(1H,s), 7.28(1H,d), 7.58(1H,s)ppm

Workup

  1. temperatureunder cooling with ice
  2. additionAfter completion of the dropwise addition
  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 s odium chloride aqueous solution and then dried over anhydrous sodium 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-b90aaaf7b1b54af9a1755ba10295303f
Source dataset
uspto-grants-2000_10
Patent number
US06130187

Reaction notes

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