Potassium Carbonate → HCID 82881970, compound

HRID 1848728Notes

Reaction equation

HRID 1848728 reaction equation
Cl[CH2:2][C:3]1[CH:7]=[CH:6][N:5]([CH3:8])[N:4]=1.C([O-])([O-])=O.[K+].[K+].[F:15][C:16]1[CH:17]=[C:18]([OH:25])[CH:19]=[CH:20][C:21]=1[N+:22]([O-:24])=[O:23]>C(#N)C>[F:15][C:16]1[CH:17]=[C:18]([CH:19]=[CH:20][C:21]=1[N+:22]([O-:24])=[O:23])[O:25][CH2:2][C:3]1[CH:7]=[CH:6][N:5]([CH3:8])[N:4]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 4239233-(Chloromethyl)-1-methyl-1H-pyrazoleHCID 5209483-Fluoro-4-nitrophenol

Product 1

HCID 82881970HCID 82881970, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 3-(chloromethyl)-1-methyl-1H-pyrazole (15.6 g, 0.12 mol) in acetonitrile (200 mL) was added K2CO3 (67 g, 0.48 mol) followed by 3-fluoro-4-nitrophenol (19 g, 0.12 mol). The mixture was stirred at 90° Celsius overnight. When the reaction was complete, it was cooled to RT and the solvent was concentrated to dryness. The resulting residue was dissolved in DCM (500 mL) and then washed with water (500 mL). The organic phase was separated, concentrated to dryness and purified by recrystallization from ethyl acetate (100 mL) to give the title compound. MS (ESI): mass calcd. for C11H10FN3O3, 251.07; m/z found, 252.2 [M+H]+. 1H NMR (300 MHz, CDCl3) δ 8.05-7.99 (t, 1H), 7.33 (d, J=3, 1H), 6.86-6.84 (m, 1H), 6.81-6.78 (m, 1H), 6.29 (d, J=3, 1H), 5.11 (s, 2H), 3.88 (s, 3H).

Workup

  1. temperatureit was cooled to RT
  2. concentrationthe solvent was concentrated to dryness
  3. dissolutionThe resulting residue was dissolved in DCM (500 mL)
  4. washwashed with water (500 mL)
  5. customThe organic phase was separated
  6. concentrationconcentrated to dryness
  7. custompurified by recrystallization from ethyl acetate (100 mL)

Sources & evidence

ORD record
ord-84607f07406448a7917f74b1798bf1fe
Source dataset
uspto-grants-2015_02
Patent number
US08952177B2

Reaction notes

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