Hydrochloric Acid → HCID 17862367, compound

HRID 644841Notes

Reaction equation

HRID 644841 reaction equation
[H-].[Na+].[OH:3][C:4]1[CH:8]=[C:7]([CH3:9])[NH:6][N:5]=1.Cl[C:11]1[C:16]([Cl:17])=[CH:15][C:14]([Cl:18])=[CH:13][N:12]=1.Cl>CN(C=O)C>[Cl:17][C:16]1[C:11]([O:3][C:4]2[CH:8]=[C:7]([CH3:9])[NH:6][N:5]=2)=[N:12][CH:13]=[C:14]([Cl:18])[CH:15]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 27666Pyridine, 2,3,5-trichloro-HCID 3197713H-Pyrazol-3-one, 2,4-dihydro-5-methyl-

Product 1

HCID 17862367HCID 17862367, compoundYield 57.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

Sodium hydride (60% in oil, 0.2 g, 5.5 mmol) was added to a solution of 3-hydroxy-5-methylpyrazole (0.49 g, 5.0 mmol) in DMF (10 ml) at 0° C., and the mixture was stirred for 30 minutes while it was allowed to have room temperature gradually. Then, 2,3,5-trichloropyridine (0.9 g, 5.0 mmol) was added, and the mixture was stirred under heating at 70° C. for 2 days. After completion of the reaction, the reaction mixture was poured into 2N hydrochloric acid (20 ml) and extracted with ethyl acetate (10 ml×3). An organic layer was washed with water, dried over anhydrous magnesium sulfate and filtered to remove a desiccant, and the solvent was distilled off from the filtrate under reduced pressure. The resultant crude product was purified with a silica gel column (ethyl acetate/hexane=1/7→1/2), to give a white solid of 3-(3,5-dichloropyridin-2-yloxy)-5-methylpyrazole (0.7 g, yield: 57.4%). mp: 109-111° C.; 1H-NMR (CDCl3, TMS, ppm): δ 2.32 (s, 3H), 5.86 (s, 1H), 7.77 (d, J=2.3 Hz, 1H), 8.03 (d, J=2.3 Hz, 1H), 9.40-11.50 (br s, 1H).

Workup

  1. customto have room temperature
  2. stirringthe mixture was stirred
  3. customAfter completion of the reaction
  4. extractionextracted with ethyl acetate (10 ml×3)
  5. washAn organic layer was washed with water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. customto remove a desiccant, and the solvent
  9. distillationwas distilled off from the filtrate under reduced pressure
  10. customThe resultant crude product was purified with a silica gel column (ethyl acetate/hexane=1/7→1/2)

Sources & evidence

ORD record
ord-f36abeba70b74d81b3f640463f22f904
Source dataset
uspto-grants-2010_04
Patent number
US07700786B2

Reaction notes

Loading…