Dimethyl Sulfoxide → HCID 21427004, compound

HRID 437752Notes

Reaction equation

HRID 437752 reaction equation
[F:1][C:2]1[C:3](=[O:9])[NH:4][C:5](=[O:8])[NH:6][CH:7]=1.CS(C)=O.[C:14]1([N:20]=[C:21]=[O:22])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>C(O)C>[F:1][C:2]1[C:3](=[O:9])[N:4]([C:5](=[O:8])[NH2:6])[C:21](=[O:22])[N:20]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:7]=1

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 33855-FluorouracilHCID 7672Phenyl isocyanate

Product 1

HCID 21427004HCID 21427004, compoundYield 81.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

10.4 g. (0.08 mole) of 5-fluorouracil was dissolved in 100 ml. of dimethyl sulfoxide, then 14.3 g. (0.12 mole) of phenyl isocyanate was added thereto and stirred at room temperature for 1 hour. The milky reaction mixture was filtered off and a fine precipitate was obtained. The precipitate was suspended in hot ethanol and again filtered. There was obtained 16.2 g. (81.4% yield) of 5-fluoro-1-phenyl carbamoyluracil melting at 280° C.

Workup

  1. customThe milky reaction mixture
  2. filtrationwas filtered off
  3. customa fine precipitate was obtained
  4. filtrationagain filtered
  5. customThere was obtained 16.2 g

Sources & evidence

ORD record
ord-1b8ff4225e6c443cacbd934f96735b22
Source dataset
uspto-grants-1977_06
Patent number
US04032524

Reaction notes

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