Iodine → Trifluoromethyluracil

HRID 1734117Notes

Reaction equation

HRID 1734117 reaction equation
II.S(=O)(=O)(O)O.[F:8][C:9]([F:19])([F:18])[CH:10]1[CH2:15][NH:14][C:13](=[O:16])[NH:12][C:11]1=[O:17].S([O-])([O-])=O.[Na+].[Na+]>CS(C)=O>[F:18][C:9]([F:8])([F:19])[C:10]1[C:11](=[O:17])[NH:12][C:13](=[O:16])[NH:14][CH:15]=1

Participants

6

Reactant 4

HCID 807Iodine2×HCID 1118Sulfuric AcidHCID 56385-(Trifluoromethyl)dihydropyrimidine-2,4(1H,3H)-dioneHCID 24437Sodium Sulfite

Product 1

HCID 5899TrifluoromethyluracilYield 60.6%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
140 °C

Procedure

In 93.6 ml of dimethylsulfoxide, 17.2 g of iodine and 3.6 ml of concentrated sulfuric acid were dissolved, and 25.2 g of 5-trifluoromethyl-5,6-dihydrouracil was added to obtain a uniform solution. The solution was stirred at 140° C. for 4 hours. The resulting mixture was allowed to cool to room temperature and 500 g of 3% aqueous sodium sulfite solution was added to reduce the iodine. The resultant was concentrated under reduced pressure and the obtained residue was dissolved in 150 ml of hot water. The resulting mixture was refrigerated for 2 days and the precipitated white needle-shaped crystals were collected by filtration and dried to obtain 15.1 g of 5-trifluoromethyluracil.

Workup

  1. customto obtain a uniform solution
  2. temperatureto cool to room temperature
  3. concentrationThe resultant was concentrated under reduced pressure
  4. dissolutionthe obtained residue was dissolved in 150 ml of hot water
  5. waitThe resulting mixture was refrigerated for 2 days
  6. filtrationthe precipitated white needle-shaped crystals were collected by filtration
  7. customdried

Sources & evidence

ORD record
ord-f8e8a9b9619d4f32b427a5349028cc1b
Source dataset
uspto-grants-1996_07
Patent number
US05532349

Reaction notes

Loading…