N-Iodosuccinimide → HCID 178517797, compound

HRID 877913Notes

Reaction equation

HRID 877913 reaction equation
[F:1][C:2]([F:11])([F:10])[C:3]1[C:4]([OH:9])=[N:5][CH:6]=[CH:7][CH:8]=1.[I:12]N1C(=O)CCC1=O.C([O-])(O)=O.[Na+]>CC#N.CN(C=O)C>[I:12][C:7]1[CH:8]=[C:3]([C:2]([F:1])([F:10])[F:11])[C:4]([OH:9])=[N:5][CH:6]=1

Participants

6

Reactant 3

HCID 120273N-IodosuccinimideHCID 516892Sodium BicarbonateHCID 36784112(1H)-Pyridinone, 3-(trifluoromethyl)-

Product 1

HCID 178517797HCID 178517797, compoundYield 81.9%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

3-trifluoromethyl-2-pyridinol (25 g, 153.3 mmol) is dissolved in anhydrous CH3CN (150 mL) and DMF (150 mL). N-iodosuccinimide (34.5 g, 153 mmol) is then added. The reaction mixture is stirred at 80° C. for 2 hours and cooled to room temperature. Aqueous 1 M NaHCO3 (150 mL) is then added to the cooled mixture. After stirring for 5 min, the solvents are evaporated to dryness. Water is added and the aqueous phase is extracted (×2) with dichloromethane. The organic phase is then evaporated and the desired product is recrystallized in water to afford 36.2 g (81%) of a white powder.

Workup

  1. temperaturecooled to room temperature
  2. stirringAfter stirring for 5 min
  3. customthe solvents are evaporated to dryness
  4. additionWater is added
  5. extractionthe aqueous phase is extracted (×2) with dichloromethane
  6. customThe organic phase is then evaporated
  7. customthe desired product is recrystallized in water

Sources & evidence

ORD record
ord-4d4d028115a842858d6b89c6e040c15e
Source dataset
uspto-grants-2015_03
Patent number
US08987452B2

Reaction notes

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