Water → HCID 68209594, compound

HRID 715918Notes

Reaction equation

HRID 715918 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[C:9](=[O:11])[CH3:10].[NH:12]1[CH:16]=[CH:15][N:14]=[N:13]1.C(=O)([O-])[O-].[K+].[K+].O>CN1CCCC1=O.C(OCC)(=O)C>[F:8][C:5]1[CH:6]=[CH:7][C:2]([N:13]2[N:14]=[CH:15][CH:16]=[N:12]2)=[C:3]([C:9](=[O:11])[CH3:10])[CH:4]=1

Participants

7

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 747941-(2,5-Difluorophenyl)ethan-1-oneHCID 178418936HCID 178418936, compound

Product 1

HCID 68209594HCID 68209594, compoundYield 26.6%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
140 °C

Procedure

1-(2,5-Difluorophenyl)ethanone (3.00 g) and 1H-triazole (1.99 g) were dissolved in N-methylpyrrolidone (5 ml). To the solution, potassium carbonate (2.66 g) was added, and the mixture was stirred at 140° C. for 4.5 hours. After standing to cool, water and ethyl acetate were added to the reaction solution to separate the aqueous and organic layers. The aqueous layer was subjected to extraction with ethyl acetate. The organic layers were combined, washed three times with saturated saline, dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (n-hexane-ethyl acetate) to obtain the title compound (1.05 g).

Workup

  1. temperatureto cool
  2. customto separate the aqueous and organic layers
  3. extractionThe aqueous layer was subjected to extraction with ethyl acetate
  4. washwashed three times with saturated saline
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe obtained residue was purified by silica gel column chromatography (n-hexane-ethyl acetate)

Sources & evidence

ORD record
ord-0e7b46e1e3334e92a86d4b73939f2ccb
Source dataset
uspto-grants-2015_11
Patent number
US09187489B2

Reaction notes

Loading…