5-Fluorouracil → 1-PYRIMIDINECARBOXAMIDE, 5-FLUORO-1,3-DIHYDRO-N-

HRID 1834768Notes

Reaction equation

HRID 1834768 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:18]=[C:19]=[O:20])[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17]>CC(N(C)C)=O>[CH2:10]([NH:18][C:19]([N:6]1[CH:7]=[C:2]([F:1])[C:3](=[O:9])[NH:4][C:5]1=[O:8])=[O:20])[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17]

Participants

4

Reactant 2

HCID 33855-FluorouracilHCID 76616Octyl isocyanate

Product 1

HCID 1165431-PYRIMIDINECARBOXAMIDE, 5-FLUORO-1,3-DIHYDRO-N-Yield 43.2%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

40 ml of dimethyl acetamide was added to 10.01 g of 5-fluorouracil and 11.95g of n-octyl isocyanate. After the reaction was carried out at 60° C for an hour, the reaction mixture was allowed to stand overnight at room temperature. The solvent was distilled off and to the residue were added 200 ml of chloroform and 300 ml of water to effect extraction. The chloroform layer was dried over anhydrous sodium sulfate. After evaporating off the chloroform, the precipitated crystals were recrystallized from ethanol to obtain 9.49 g of 1-(N-n-octylcarbamoyl)-5-fluorouracil melting at 98°-100° C.

Workup

  1. waitAfter the reaction was carried out at 60° C for an hour
  2. distillationThe solvent was distilled off and to the residue
  3. additionwere added 200 ml of chloroform and 300 ml of water
  4. extractionextraction
  5. dry with materialThe chloroform layer was dried over anhydrous sodium sulfate
  6. customAfter evaporating off the chloroform
  7. customthe precipitated crystals were recrystallized from ethanol

Sources & evidence

ORD record
ord-476fd085617a49fcb491d306799340fc
Source dataset
uspto-grants-1978_01
Patent number
US04071519

Reaction notes

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