5-Fluorouracil → Carmofur

HRID 1834767Notes

Reaction equation

HRID 1834767 reaction equation
[F:1][C:2]1[C:3](=[O:9])[NH:4][C:5](=[O:8])[NH:6][CH:7]=1.[CH2:10]([N:16]=[C:17]=[O:18])[CH2:11][CH2:12][CH2:13][CH2:14][CH3:15]>CC(N(C)C)=O>[F:1][C:2]1[C:3](=[O:9])[NH:4][C:5](=[O:8])[N:6]([C:17](=[O:18])[NH:16][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15])[CH:7]=1

Participants

4

Reactant 2

HCID 33855-FluorouracilHCID 75659Hexyl isocyanate

Product 1

HCID 2577CarmofurYield 75%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
50 °C

Procedure

13.0g (0.10 mole) of 5-fluorouracil was suspended in 60 ml of dimethyl acetamide, then 14.0g (0.11 mole) of n-hexyl isocyanate was added thereto at room temperature and stirred at 50° C for 8 hours. After the reaction mixture was concentrated under reduced pressure, the residue was poured into 400 ml of water and resultant precipitate was filtered off. The precipitate was washed and dried and 19.3g (75.0% yield) of 5-fluoro-1-(n-hexylcarbamoyl)uracil was obtained.

Workup

  1. concentrationAfter the reaction mixture was concentrated under reduced pressure
  2. additionthe residue was poured into 400 ml of water and resultant precipitate
  3. filtrationwas filtered off
  4. washThe precipitate was washed
  5. customdried

Sources & evidence

ORD record
ord-32199e7ae65a4ff194f679bb9b1f5b97
Source dataset
uspto-grants-1978_01
Patent number
US04071519

Reaction notes

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