Chlorodifluoromethane → HCID 18425025, compound

HRID 1280320Notes

Reaction equation

HRID 1280320 reaction equation
[OH-].[Na+].[Cl:3][C:4]1[C:17]([Cl:18])=[CH:16][CH:15]=[CH:14][C:5]=1[CH2:6][C:7]1[NH:11][N:10]([CH3:12])[C:9](=[O:13])[CH:8]=1.Cl[CH:20]([F:22])[F:21]>O.O1CCOCC1>[Cl:3][C:4]1[C:17]([Cl:18])=[CH:16][CH:15]=[CH:14][C:5]=1[CH2:6][C:7]1[N:11]([CH:20]([F:22])[F:21])[N:10]([CH3:12])[C:9](=[O:13])[CH:8]=1

Participants

6

Reactant 3

HCID 6372ChlorodifluoromethaneHCID 14798Sodium HydroxideHCID 11807320HCID 11807320, compound

Product 1

HCID 18425025HCID 18425025, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of 19 g (0.48 mol) of sodium hydroxide in 165 ml of water was added to a solution of 24.5 g (95.3 mmol) of 5-(2,3-dichlorobenzyl)-1,2-dihydro-2-methyl-3H-pyrazol-3-one in 200 ml of dioxane. The mixture was subsequently heated to 60—65° C. and gaseous chlorodifluoromethane was passed through until the starting material had been completely consumed (after about 2 hours). The reaction mixture was then poured into 500 ml of water. The product was extracted with methyl tert-butyl ether. The organic phase was finally dried over magnesium sulfate and concentrated. The crude product was purified by silica gel chromatography (eluent: hexane/ethyl acetate=1:1). Yield: at first 11.5 g of compound Ic.1 and thereafter 5.8 g of compound IIIc.1;

Workup

  1. temperatureThe mixture was subsequently heated to 60—65° C.
  2. customhad been completely consumed (after about 2 hours)
  3. additionThe reaction mixture was then poured into 500 ml of water
  4. extractionThe product was extracted with methyl tert-butyl ether
  5. dry with materialThe organic phase was finally dried over magnesium sulfate
  6. concentrationconcentrated
  7. customThe crude product was purified by silica gel chromatography (eluent: hexane/ethyl acetate=1:1)

Sources & evidence

ORD record
ord-f2f2a126ec624631ad8dd5ff1a40d227
Source dataset
uspto-grants-2002_09
Patent number
US06451734B1

Reaction notes

Loading…