5-Fluorouracil → HCID 12370701, compound

HRID 437754Notes

Reaction equation

HRID 437754 reaction equation
[F:1][C:2]1[C:3](=[O:9])[NH:4][C:5](=[O:8])[NH:6][CH:7]=1.[H-].[Na+].[CH2:12]([N:14]([CH2:18][CH3:19])[C:15](Cl)=[O:16])[CH3:13]>CC(N(C)C)=O>[CH2:12]([N:14]([CH2:18][CH3:19])[C:15]([N:6]1[CH:7]=[C:2]([F:1])[C:3](=[O:9])[NH:4][C:5]1=[O:8])=[O:16])[CH3:13]

Participants

5

Reactant 3

HCID 33855-FluorouracilHCID 6916Diethylcarbamoyl chlorideHCID 24758Sodium hydride

Product 1

HCID 12370701HCID 12370701, compoundYield 75.5%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent2×

Conditions

Temperature
30 °C

Procedure

1.3 g. (0.01 mole) of 5-fluorouracil was dissolved in 20 ml. of dimethyl acetamide and then 0.48 g. (0.01 mole) of 50% sodium hydride was added thereto. Subsequently, 1.36 g. (0.01 mole) of N,N-diethylcarbamoyl chloride in 5 ml. of dimethyl acetamide was added dropwise at 30° C. After stirring at 30° C. for 5 hours, the reaction mixture was allowed to stand overnight at room temperature. The reaction mixture was filtered and the resultant filtrate was evaporated under reduced pressure. The residue obtained was extracted with 30 ml. of chloroform and the extract was concentrated to dryness to give 2.14 g. of crude product. The product was washed with diethyl ether and 1.73 g. (75.5% yield) of 1-(N,N-diethylcarbamoyl)-5-fluorouracil melting at 157°-160° C. was obtained.

Workup

  1. waitto stand overnight at room temperature
  2. filtrationThe reaction mixture was filtered
  3. customthe resultant filtrate was evaporated under reduced pressure
  4. customThe residue obtained
  5. extractionwas extracted with 30 ml
  6. concentrationof chloroform and the extract was concentrated to dryness
  7. customto give 2.14 g
  8. washThe product was washed with diethyl ether and 1.73 g

Sources & evidence

ORD record
ord-a940d65182864cb69bebaf25c988024d
Source dataset
uspto-grants-1977_06
Patent number
US04032524

Reaction notes

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