5-Fluorouracil → Tegafur

HRID 127690Notes

Reaction equation

HRID 127690 reaction equation
[F:1][C:2]1[C:3](=[O:9])[NH:4][C:5](=[O:8])[NH:6][CH:7]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1.[O:21]1[CH:25]=[CH:24][CH2:23][CH2:22]1>N1C=CC=CC=1>[O:21]1[CH2:25][CH2:24][CH2:23][CH:22]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-FluorouracilHCID 6101p-Toluenesulfonic acidHCID 709342,3-Dihydrofuran2×

Product 1

HCID 5386Tegafur

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Procedure

In 50 ml of pyridine were dissolved 2.5 g of 5-fluorouracil and 0.4 g of p-toluenesulfonic acid. To this solution were added 1.5 ml of 2,3-dihydrofuran and the mixture was reacted for 6 hours at 120° C. in an oil bath. Further, 3 ml of 2,3-dihydrofuran in 4 portions were added and the mixture was reacted for 15 hours. After completion of the reaction, pyridine was removed from the reaction liquid by distillation and the residue was dissolved in 100 ml of chloroform and filtered to separate insoluble matters. The filtrate was washed with water, dried and concentrated by removing chloroform by distillation. The precipitated crystals were collected by filtration, washed with a small amount of ether and dried to obtain 2.0 g of 1-(2-tetrahydrofuryl)-5-fluorouracil. The crystals had a melting point of 167°-168° C. and were identical in IR-absorption spectra with the standard sample.

Workup

  1. customthe mixture was reacted for 6 hours at 120° C. in an oil bath
  2. customthe mixture was reacted for 15 hours
  3. customwas removed from the reaction liquid by distillation
  4. dissolutionthe residue was dissolved in 100 ml of chloroform
  5. filtrationfiltered
  6. customto separate insoluble matters
  7. washThe filtrate was washed with water
  8. customdried
  9. concentrationconcentrated
  10. customby removing chloroform
  11. distillationby distillation
  12. filtrationThe precipitated crystals were collected by filtration
  13. washwashed with a small amount of ether
  14. customdried

Sources & evidence

ORD record
ord-afcbbfc51f474b73abae2c7b055a3f27
Source dataset
uspto-grants-1981_03
Patent number
US04256885

Reaction notes

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