Water → HCID 15030566, compound

HRID 1738363Notes

Reaction equation

HRID 1738363 reaction equation
Cl[CH:2]([F:4])[F:3].[Cl:5][C:6]1[C:11]([CH3:12])=[CH:10][C:9]([C:13]2[NH:17][N:16]([CH3:18])[C:15](=[O:19])[CH:14]=2)=[C:8]([F:20])[CH:7]=1.[OH-].[Na+].O>O1CCOCC1>[Cl:5][C:6]1[C:11]([CH3:12])=[CH:10][C:9]([C:13]2[CH:14]=[C:15]([O:19][CH:2]([F:4])[F:3])[N:16]([CH3:18])[N:17]=2)=[C:8]([F:20])[CH:7]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 6372ChlorodifluoromethaneHCID 14798Sodium HydroxideHCID 21266768HCID 21266768, compound

Product 1

HCID 15030566HCID 15030566, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Gaseous chlorodifluoromethane was passed at room temperature for 2 hours into a solution of 133 g (0.55 mol) of 5-(4-chloro-2-fluoro-5-methylphenyl)-1,2-dihydro-2-methyl-3H-pyrazol-3-one and 110 g (2.7 mol) of sodium hydroxide in 1 l of dioxane and 0.5 1 of water. The reaction solution was then poured into 2 l of water, whereupon the aqueous phase was extracted three times using ethyl acetate. The combined organic phases were dried over magnesium sulfate and then filtered and concentrated. The residue was purified by means of column chromatography on silica gel (eluent: cyclohexane/ethyl acetate=9:1), followed by preparative MPLC on silica gel (same eluent). Yield: 43 g.

Workup

  1. extractionwas extracted three times
  2. dry with materialThe combined organic phases were dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by means of column chromatography on silica gel (eluent: cyclohexane/ethyl acetate=9:1)

Sources & evidence

ORD record
ord-207a77b2d12749e8874fbc1b1420c4bd
Source dataset
uspto-grants-1999_10
Patent number
US05962694

Reaction notes

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