5-Fluorouracil → Tegafur

HRID 127693Notes

Reaction equation

HRID 127693 reaction equation
[F:1][C:2]1[C:3](=[O:9])[NH:4][C:5](=[O:8])[NH:6][CH:7]=1.[Cl-].[Al+3].[Cl-].[Cl-].[O:14]1[CH:18]=[CH:17][CH2:16][CH2:15]1>N1C=CC=CC=1>[O:14]1[CH2:18][CH2:17][CH2:16][CH:15]1[N:6]1[CH:7]=[C:2]([F:1])[C:3](=[O:9])[NH:4][C:5]1=[O:8]

Participants

5

Reactant 3

HCID 33855-Fluorouracil2×HCID 709342,3-DihydrofuranHCID 6451240Aluminum(III) Chloride

Product 1

HCID 5386TegafurYield 75.4%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

In 50 ml of pyridine were dissolved 2.5 g of 5-fluorouracil and 0.35 g of anhydrous aluminum chloride. To this solution were added 2.3 ml of 2,3-dihydrofuran and the mixture was reacted at 120° C. for 6 hours. A part of the reaction liquid was extracted and subjected to thin layer chromatography to observe the state of proceeding of the reaction whereby the composition of the product was 70% of the end product, 10% of by-products and less than 1% of unreacted 5-fluorouracil. The pyridine was distilled off from the reaction liquid and the residue was shaken with 50 ml of chloroform and a small amount of water and the mixture was separated. The chloroform layer was dried and the chloroform was distilled off. The precipitated crystals were collected by filtration, washed with ether and dried to obtain 2.9 g of 1-(2-tetrahydrofuryl)-5-fluorouracil in a yield of 75.4%, which had a melting point of 167°-168° C.

Workup

  1. customthe mixture was reacted at 120° C. for 6 hours
  2. customA part of the reaction liquid
  3. extractionwas extracted
  4. customthe state of proceeding of the reaction whereby the composition of the product
  5. distillationThe pyridine was distilled off from the reaction liquid
  6. customa small amount of water and the mixture was separated
  7. dry with materialThe chloroform layer was dried
  8. distillationthe chloroform was distilled off
  9. filtrationThe precipitated crystals were collected by filtration
  10. washwashed with ether
  11. customdried

Sources & evidence

ORD record
ord-00097dc6dd854b0f893820b575593141
Source dataset
uspto-grants-1981_03
Patent number
US04256885

Reaction notes

Loading…