Hydrochloric Acid → HCID 15477254, compound

HRID 366333Notes

Reaction equation

HRID 366333 reaction equation
[Cl:1][C:2]1[C:7]2[CH:8]=[C:9]([CH3:11])[O:10][C:6]=2[C:5]([N:12]2[C:17](=[O:18])[CH:16]=[C:15]([C:19]([F:22])([F:21])[F:20])[N:14]([CH3:23])[C:13]2=[O:24])=[C:4]([F:25])[CH:3]=1.[Cl-].[Al+3].[Cl-].[Cl-].[C:30](Cl)(=[O:32])[CH3:31].Cl>[N+](C)([O-])=O>[C:30]([C:8]1[C:7]2[C:2]([Cl:1])=[CH:3][C:4]([F:25])=[C:5]([N:12]3[C:17](=[O:18])[CH:16]=[C:15]([C:19]([F:22])([F:20])[F:21])[N:14]([CH3:23])[C:13]3=[O:24])[C:6]=2[O:10][C:9]=1[CH3:11])(=[O:32])[CH3:31]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6367Acetyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 15477207HCID 15477207, compound

Product 1

HCID 15477254HCID 15477254, compoundYield 68.2%

Reagents, catalysts & solvents 1

HCID 6375NitromethaneSolvent

Procedure

1.6 g (4.2 mmol) of 3-(4-chloro-6-fluoro-2-methylbenzofuran-7-yl)-1-methyl-6-trifluoromethyluracil was dissolved in 50 ml of nitromethane, and 5.6 g (42 mmol) of aluminum chloride was added thereto at room temperature. Further, 3.3 g (42 mmol) of acetyl chloride was dropwise added thereto. After completion of the dropwise addition, stirring was carried out for 5 hours under heating and ref refluxing. 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 sodium 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 1.2 g (yield: 66.7%) of the desired product as pale yellow crystals. Melting point: 138-140° C.

Workup

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

Sources & evidence

ORD record
ord-7e047feee90f498f86722fb4d52de87c
Source dataset
uspto-grants-2000_10
Patent number
US06130187

Reaction notes

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