Hydrofluoric Acid → 5-Fluorouracil

HRID 1112490Notes

Reaction equation

HRID 1112490 reaction equation
[NH:1]1[CH:8]=[CH:7][C:5](N)=[N:4][C:2]1=[O:3].FS(O)(=O)=[O:11].[F].[FH:15]>>[F:15][C:7]1[C:5](=[O:11])[NH:4][C:2](=[O:3])[NH:1][CH:8]=1

Participants

4

Reactant 3

HCID 14917Hydrofluoric AcidHCID 178418229CytosineHCID 178527664HCID 178527664, compound

Product 1

HCID 33855-Fluorouracil

Procedure

Into a solution of cytosine (11.1 g) in hydrogen fluoride (50 ml) kept at 5° C., fluorine fluorosulfonate was blown while stirring. The cytosine was completely consumed in 2 hours, and the total amount of fluorine fluorosulfonate was 0.21 mol. The reaction mixture was heated to distill out the hydrogen fluoride, water (100 ml) was added thereto, and the resulting mixture was heated under reflux for 2 hours. An aqueous solution of calcium hydroxide was added thereto to make pH 6, and precipitated materials were eliminated by filtration. The filtrate was cooled, and the separated crystals were collected by filtration to give 5-fluorouracil (9.9 g). Yield, 76.2%.

Workup

  1. customkept at 5° C.
  2. customThe cytosine was completely consumed in 2 hours
  3. temperatureThe reaction mixture was heated
  4. distillationto distill out the hydrogen fluoride, water (100 ml)
  5. additionwas added
  6. temperaturethe resulting mixture was heated
  7. temperatureunder reflux for 2 hours
  8. additionAn aqueous solution of calcium hydroxide was added
  9. customprecipitated materials
  10. filtrationwere eliminated by filtration
  11. temperatureThe filtrate was cooled
  12. filtrationthe separated crystals were collected by filtration

Sources & evidence

ORD record
ord-e467c5f2feb148d2a1c9af2ab9cf6254
Source dataset
uspto-grants-1978_10
Patent number
US04122251

Reaction notes

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