Uracil → 5-Fluorouracil

HRID 2082665Notes

Reaction equation

HRID 2082665 reaction equation
C(F)(F)=C(Cl)[F:3].[NH:7]1[CH:14]=[CH:13][C:11](=[O:12])[NH:10][C:8]1=[O:9].FF>F>[F:3][C:13]1[C:11](=[O:12])[NH:10][C:8](=[O:9])[NH:7][CH:14]=1

Participants

5

Reactant 3

HCID 1174Uracil2×HCID 6594Chlorotrifluoroethylene2×HCID 24524Fluorine

Product 1

HCID 33855-Fluorouracil

Reagents, catalysts & solvents 1

HCID 14917Hydrofluoric AcidSolvent2×

Procedure

In a 200 ml volume flask made from "Daiflon Resin" (trifluorochloroethylene resin manufactured by Daikin Kogyo Co., Ltd.) which is equipped with a stirrer, a cooler, an inlet for gas and a thermometer, a designed amount of uracil and an aqueous solution of hydrofluoric acid (50 g) are charged, and the contents are stirred at a temperature lower than the reaction temperature to dissolve uracil in the aqueous solution of hydrofluoric acid. A designed amount of fluorine gas diluted or not with nitrogen gas is introduced therein over a period of 30 minutes to 1 hour. Then, nitrogen gas is made to pass through the flask for about 10 minutes to remove fluorine present in the reaction system. The reaction solvent is distilled off with heating to obtain crude 5-fluorouracil.

Workup

  1. customis equipped with a stirrer
  2. additionis introduced
  3. waitover a period of 30 minutes to 1 hour
  4. customto remove fluorine
  5. distillationThe reaction solvent is distilled off
  6. temperaturewith heating

Sources & evidence

ORD record
ord-076612d93bbc4af0b58dd6614efdc462
Source dataset
uspto-grants-1978_04
Patent number
US04082752

Reaction notes

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