5-Fluorouracil → HCID 13014273, compound

HRID 2286697Notes

Reaction equation

HRID 2286697 reaction equation
[F:1][C:2]1[C:3](=[O:9])[NH:4][C:5](=[O:8])[NH:6][CH:7]=1.[H-].[Na+].[C:12]([O:15][CH2:16]Cl)(=[O:14])[CH3:13]>CC(N(C)C)=O>[C:12]([O:15][CH2:16][N:6]1[CH:7]=[C:2]([F:1])[C:3](=[O:9])[N:4]([CH2:16][O:15][C:12](=[O:14])[CH3:13])[C:5]1=[O:8])(=[O:14])[CH3:13]

Participants

5

Reactant 3

HCID 33855-FluorouracilHCID 24758Sodium hydrideHCID 69366Chloromethyl acetate

Product 1

HCID 13014273HCID 13014273, compoundYield 6.6%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent2×

Procedure

In 70 ml of dimethylacetamide was dissolved 2.60 g (0.02 mol) of 5-fluorouracil. To this solution were added 0.96 g (0.02 mol) of 50% sodium hydride and then a solution of 2.16 g (0.02 mol) of chloromethyl acetate in 10 ml of dimethylacetamide. The mixture was reacted together at room temperature for 5.5 hours. After completion of the reaction, the reaction liquid was filtered to remove a precipitate and then the dimethylacetamide used as solvent was removed from the filtrate by distillation. The residue was taken up in 100 ml of ether and the ethereal solution was filtered to remove insoluble matters. The ether was removed by distillation and the residue was subjected to an adsorption treatment using a column packed with silica gel. The adsorbed substance was elutriated with a mixture (1:1 in mixing ratio) of benzene and ethyl acetate to isolate at first 180 mg of 1,3-bis(acetoxymethyl)-5-fluorouracil in a yield of 3.2%. This product was a viscous liquid and exhibited in IR-absorption spectral analysis characteristic absorption bands at 3120, 2970, 1755(s), 1704(s), 1690(s), 1478, 1375, 1285, 1230(s), 1170, 1087, 1035(s), 980, 842, 790 and 772 cm-1.

Workup

  1. customThe mixture was reacted together at room temperature for 5.5 hours
  2. customAfter completion of the reaction
  3. customthe reaction liquid
  4. filtrationwas filtered
  5. customto remove a precipitate
  6. customwas removed from the filtrate by distillation
  7. filtrationthe ethereal solution was filtered
  8. customto remove insoluble matters
  9. customThe ether was removed by distillation

Sources & evidence

ORD record
ord-6bfefbcccdb24540a11f1efeba84a5d4
Source dataset
uspto-grants-1981_05
Patent number
US04267326

Reaction notes

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