Dimethylformamide → HCID 14555275, compound

HRID 1723480Notes

Reaction equation

HRID 1723480 reaction equation
[H-].[Na+].C[N:4]([CH3:7])[CH:5]=[O:6].[CH:8]1[C:13]([OH:14])=[CH:12][CH:11]=[C:10]([F:15])[CH:9]=1.Cl[C:17]1[N:25]=[CH:24][CH:23]=[CH:22][C:18]=1C(N)=O>C(OCC)C.O>[F:15][C:10]1[CH:11]=[CH:12][C:13]([CH2:7][NH:4][C:5](=[O:6])[C:23]2[CH:22]=[CH:18][CH:17]=[N:25][C:24]=2[O:14][C:13]2[CH:12]=[CH:11][C:10]([F:15])=[CH:9][CH:8]=2)=[CH:8][CH:9]=1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 97324-FluorophenolHCID 24758Sodium hydrideHCID 825882-Chloronicotinamide

Product 1

HCID 14555275HCID 14555275, compoundYield 25.95%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

Sodium hydride dispersion, 60% by weight (167 mg, 4.2 mmol) and 25 ml dimethylformamide (DMF) is placed in a 65 ml round bottom flask equipped with a stir bar and a reflux condenser under nitrogen. P-fluorophenol (430 mg, 3.8 mmol) is added to the reaction mixture and stirred for one hour. The chloronicotinamide (850 mg, 3.2 mmol) is then added and the reaction heated to reflux for 16 hours. The mixture is then cooled to room temperature and poured into 50 ml of water. This is extracted with ethyl acetate (2×50 ml), and the combined organics washed with 1M NaOH (2×50 ml), water (2×50 ml) and brine (1×50 ml). The ethyl acetate is dried over anhydrous sodium sulfate, filtered and concentrated in vacuo to yield a green oil. This is digested in diethyl ether, and the resulting green crystals filtered off. The solids are recrystallized in ethanol to yield 283 mg (25.95%) of the title product as a white solid.

Workup

  1. customequipped with a stir bar and a reflux condenser under nitrogen
  2. temperaturethe reaction heated
  3. temperatureto reflux for 16 hours
  4. extractionThis is extracted with ethyl acetate (2×50 ml)
  5. washthe combined organics washed with 1M NaOH (2×50 ml), water (2×50 ml) and brine (1×50 ml)
  6. dry with materialThe ethyl acetate is dried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customto yield a green oil
  10. filtrationthe resulting green crystals filtered off
  11. customThe solids are recrystallized in ethanol

Sources & evidence

ORD record
ord-76bcd3a3f29849839e6332ff50a89a18
Source dataset
uspto-grants-1989_08
Patent number
US04861891

Reaction notes

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