Potassium Carbonate → HCID 90112556, compound

HRID 1508884Notes

Reaction equation

HRID 1508884 reaction equation
Cl[CH2:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7][OH:8])=[CH:5][CH:4]=1.[Cl:11][C:12]1[CH:13]=[N:14][NH:15][CH:16]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C.O>[Cl:11][C:12]1[CH:13]=[N:14][N:15]([CH2:2][C:3]2[CH:10]=[CH:9][C:6]([CH2:7][OH:8])=[CH:5][CH:4]=2)[CH:16]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 275241H-Pyrazole, 4-chloro-HCID 5107660[4-(Chloromethyl)phenyl]methanol

Product 1

HCID 90112556HCID 90112556, compoundYield 75%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

A mixture of 4-(chloromethyl)benzyl alcohol (0.500 g, 3.19 mmol), 4-chloro-1H-pyrazole (0.753 g, 7.34 mmol), and potassium carbonate (0.908 g, 7.02 mmol) in acetonitrile (40 mL) was stirred at rt overnight. After this time, the mixture was diluted with water and extracted with ethyl acetate. The combined organic layer was dried over anhydrous sodium sulfate, filtered and the filtrate was concentrated. The residue was purified by column chromatography (silica, hexanes/ethyl acetate) to afford the title compound (0.375 g, 75%) as a white solid. MW=222.67. 1H NMR (CDCl3, 500 MHz) δ 7.45 (s, 1H), 7.37 (s, 1H), 7.35 (s, 1H), 7.33 (s, 1H), 7.23 (s, 1H), 7.22 (s, 1H), 5.24 (s, 2H), 4.70 (d, J=5.9 Hz, 2H), 1.68 (t, J=5.9 Hz, 1H).

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe combined organic layer was dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationthe filtrate was concentrated
  5. customThe residue was purified by column chromatography (silica, hexanes/ethyl acetate)

Sources & evidence

ORD record
ord-cbdc83d4cb1244429b87e4c439215361
Source dataset
uspto-grants-2015_12
Patent number
US09221843B2

Reaction notes

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