5-Fluorouracil → 1-Benzenesulfonyl-5-fluorouracil

HRID 918394Notes

Reaction equation

HRID 918394 reaction equation
[F:1][C:2]1[C:3](=[O:9])[NH:4][C:5](=[O:8])[NH:6][CH:7]=1.C(=O)([O-])[O-].[K+].[K+].O1CCOCC1.[C:22]1([S:28](Cl)(=[O:30])=[O:29])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>C(O)C>[C:22]1([S:28]([N:6]2[CH:7]=[C:2]([F:1])[C:3](=[O:9])[NH:4][C:5]2=[O:8])(=[O:30])=[O:29])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

6

Reactant 4

HCID 33855-FluorouracilHCID 7369Benzenesulfonyl chlorideHCID 11430Potassium CarbonateHCID 312751,4-Dioxane2×

Product 1

HCID 5556221-Benzenesulfonyl-5-fluorouracilYield 54.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

2.6 g (0.02 mole) of 5-fluorouracil and 1.38 g (0.01 mole) of anhydrous potassium carbonate were suspended in 70 ml. of dioxane. 3.5 g (0.02 mole) of benzenesulfonyl chloride in 10 ml. of dioxane was dropwise added thereto and stirred at 80°C. for 7 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 a small amount of ethanol and allowed to stand at 5°C. overnight. There was obtained 2.95 g (54.6% yield) of 1-benzenesulfonyl-5-fluorouracil. The product was recrystallized from dioxane-ethanol and gave granular crystals melting at 256°-257°C. 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. waitto stand at 5°C. overnight

Sources & evidence

ORD record
ord-0596ea97426749fd835c855fd11e614c
Source dataset
uspto-grants-1976_07
Patent number
US03971784

Reaction notes

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