Chlorodifluoromethane → HCID 15030566, compound

HRID 566596Notes

Reaction equation

HRID 566596 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+]>O1CCOCC1.O>[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 3

HCID 6372ChlorodifluoromethaneHCID 14798Sodium HydroxideHCID 21266768HCID 21266768, compound

Product 1

HCID 15030566HCID 15030566, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

Gaseous chlorodifluoromethane was passed 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 l of water at room temperature. 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 (identical 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-c8b1d572b93d4a8db497307034d91ccd
Source dataset
uspto-grants-2001_01
Patent number
US06175007B1

Reaction notes

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