Chlorodifluoromethane → HCID 15220184, compound

HRID 1599982Notes

Reaction equation

HRID 1599982 reaction equation
[OH-].[Na+].[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH2:14][C:13](=[O:15])[N:12]([CH3:16])[N:11]=2)=[CH:6][CH:5]=1.Cl[CH:18]([F:20])[F:19]>O.O1CCOCC1>[Cl:3][C:4]1[CH:5]=[CH:6][C:7]([C:10]2[CH:14]=[C:13]([O:15][CH:18]([F:20])[F:19])[N:12]([CH3:16])[N:11]=2)=[CH:8][CH:9]=1

Participants

6

Reactant 3

HCID 6372ChlorodifluoromethaneHCID 14798Sodium HydroxideHCID 151450175-(4-Chlorophenyl)-2-methyl-2,4-dihydro-3H-pyrazol-3-one

Product 1

HCID 15220184HCID 15220184, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

A solution of 162 g (4.0 mol) of sodium hydroxide in l 1 of water was addedto a solution of 169.1 g (0,811 mol) of 3-(4-chlorophenyl)-1-methyl-2-pyrazolin-5-one in 2.5 1 of dioxane. Chlorodifluoromethane (about 175 g) was passed in over the course of 5 hours at 60°-65° C., after which the reaction solution was stirred into 1.5 1 of water. Extraction three times with methyl tertbutyl ether, followed by drying of the organic phase and removal of the solvent in vacuo, gave the crude product, which was purified further by chromatography on silica gel (hexane/ethyl acetate 7:3). Yield: 142.9 g; 1H-NMR (400 MHz, in CDCl3): δ [ppm]=7.60 (d,2H), 7.28 (d,2H), 6.54 (t,1H), 6.08 (s,1H), 3.69 (s,3H).

Workup

  1. customwas passed in over the course of 5 hours at 60°-65° C.
  2. extractionExtraction three times with methyl tertbutyl ether
  3. customby drying of the organic phase and removal of the solvent in vacuo

Sources & evidence

ORD record
ord-f52436a1a6964dde8c220c8c289db684
Source dataset
uspto-grants-1998_04
Patent number
US05744426

Reaction notes

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