5-Fluorouracil → HCID 20525115, compound

HRID 1702777Notes

Reaction equation

HRID 1702777 reaction equation
[C:1]([CH2:4][CH2:5][N:6]=[C:7]=[O:8])(=[O:3])[CH3:2].[F:9][C:10]1[C:11](=[O:17])[NH:12][C:13](=[O:16])[NH:14][CH:15]=1>CN(C)C(=O)C.C(OCC)(=O)C>[C:1]([CH2:4][CH2:5][NH:6][C:7]([N:14]1[CH:15]=[C:10]([F:9])[C:11](=[O:17])[NH:12][C:13]1=[O:16])=[O:8])(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 33855-FluorouracilHCID 214648874-Isocyanatobutan-2-one

Product 1

HCID 20525115HCID 20525115, compound

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 31374DimethylacetamideSolvent

Procedure

To the above solution of 2-acetylethyl isocyanate was added a solution of 5-fluorouracil (2.60 g.) in N,N-dimethylacetamide (15 ml.) at 80° C. and stirred for further 5 hours at the same temperature. The resultant mixture was diluted with ethyl acetate (200 ml.), washed with water (each 30 ml., 3 times), dried over magnesium sulfate, treated with activated charcoal, filtered and evaporated in vacuo. The residue was recrystallized from ethyl acetate to give 1-[N-(2-acetylethyl)carbamoyl]-5-fluorouracil (439 mg.).

Workup

  1. washwashed with water (each 30 ml
  2. dry with material, 3 times), dried over magnesium sulfate
  3. additiontreated with activated charcoal
  4. filtrationfiltered
  5. customevaporated in vacuo
  6. customThe residue was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-ac14c62d94a1475ca929795337f64343
Source dataset
uspto-grants-1982_09
Patent number
US04349552

Reaction notes

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