5-Fluorouracil → 1-Methylcarbamoyl-5-fluorouracil

HRID 437753Notes

Reaction equation

HRID 437753 reaction equation
[F:1][C:2]1[C:3](=[O:9])[NH:4][C:5](=[O:8])[NH:6][CH:7]=1.[CH3:10][N:11]=[C:12]=[O:13]>CS(C)=O>[F:1][C:2]1[C:3](=[O:9])[NH:4][C:5](=[O:8])[N:6]([C:12](=[O:13])[NH:11][CH3:10])[CH:7]=1

Participants

4

Reactant 2

HCID 33855-FluorouracilHCID 12228Methyl Isocyanate

Product 1

HCID 924521-Methylcarbamoyl-5-fluorouracilYield 86.1%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

10.4 g. (0.08 mole) of 5-fluorouracil and 10.0 g. (0.176 mole) of methyl isocyanate were mixed in 100 ml. of dimethyl sulfoxide and stirred at room temperature. Dimethyl sulfoxide and excess methyl isocyanate were removed from the reaction mixture by distillation. The resultant residue was washed with chloroform and dried in a vacuum oven to give 15.8 g. (86.1% yield) of 5-fluoro-1-methylcarbamoyluracil. The product was recrystallized from ethyl acetate and there were obtained white crystals melting at 277° C.

Workup

  1. customDimethyl sulfoxide and excess methyl isocyanate were removed from the reaction mixture by distillation
  2. washThe resultant residue was washed with chloroform
  3. customdried in a vacuum oven
  4. customto give 15.8 g

Sources & evidence

ORD record
ord-8fb5b8a2fbc24ff0b02f79d5f1677d5d
Source dataset
uspto-grants-1977_06
Patent number
US04032524

Reaction notes

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