Pyridine → HCID 15396960, compound

HRID 918390Notes

Reaction equation

HRID 918390 reaction equation
[F:1][C:2]1[C:3](=[O:9])[NH:4][C:5](=[O:8])[NH:6][CH:7]=1.O1CCOCC1.N1C=CC=CC=1.[CH3:22][O:23][C:24]1[CH:32]=[CH:31][C:27]([C:28](Cl)=[O:29])=[CH:26][CH:25]=1>C(O)C>[F:1][C:2]1[C:3](=[O:9])[NH:4][C:5](=[O:8])[N:6]([C:28](=[O:29])[C:27]2[CH:31]=[CH:32][C:24]([O:23][CH3:22])=[CH:25][CH:26]=2)[CH:7]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 33855-FluorouracilHCID 7477p-Anisoyl chlorideHCID 312751,4-Dioxane2×

Product 1

HCID 15396960HCID 15396960, compoundYield 49.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

1.3 g (0.01 mole) of 5-fluorouracil was suspended in a mixed solution of 40 ml. of dioxane and 2 ml. of pyridine. 1.7 g (0.01 mole) of p-methoxybenzoyl chloride in 5 ml. of dioxane was added to the suspension and stirred at 80°C. for 5 hours. The reaction mixture was cooled to room temperature and filtered. The filtrate was concentrated under reduced pressure and a resinous residue was obtained. The residue was dissolved in ethanol and filtered. After cooling to 0°C., the resulting crystals were filtered and dried to give 1.30 g (49.2% yield) of 5-fluoro-1-(p-methoxybenzoyl)uracil. The product was recrystallized from dioxane-ethanol and white needles melting at 200°-201°C. were obtained. The results of an elementary analysis thereof were well in agreement with the calculated value as follows:

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. customa resinous residue was obtained
  5. filtrationfiltered
  6. temperatureAfter cooling to 0°C.
  7. filtrationthe resulting crystals were filtered
  8. customdried

Sources & evidence

ORD record
ord-d5c2d220aa3c4e59a42e2c0387fe82e5
Source dataset
uspto-grants-1976_07
Patent number
US03971784

Reaction notes

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