1-Bromo-2-Chloroethane → HCID 20197212, compound

HRID 652416Notes

Reaction equation

HRID 652416 reaction equation
[CH3:1][CH:2]1[N:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[NH:5][C:4](=[O:13])[CH2:3]1.Br[CH2:15][CH2:16][Cl:17]>CO.C(Cl)Cl.O>[Cl:17][CH2:16][CH2:15][N:5]1[C:4](=[O:13])[CH2:3][CH:2]([CH3:1])[N:6]1[C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

6

Reactant 2

HCID 78491-Bromo-2-ChloroethaneHCID 44143303-Pyrazolidinone, 5-methyl-1-phenyl-

Product 1

HCID 20197212HCID 20197212, compoundYield 56.6%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A sodium methylate solution, obtained from 3.9 g sodium and 80 ml methanol is added to a suspension of 26.1 g 5-methyl-1-phenylpyrazolin-3-one in 200 ml methanol. After stirring for 30 minutes, 43.02 g 1-bromo-2-chloroethane are added to the clear solution at ambient temperature. The reaction mixture is heated for 15 hours under reflux. Then the solvent is drawn off under reduced pressure. The residue which remains is dissolved in 250 ml methylene chloride and 100 ml water. The organic phase is separated off, dried over sodium sulphate, filtered, and the solvent is evaporated off under reduced pressure. The residue is dissolved in ethyl ether, and the solution is filtered to remove the remaining initial material. Then the solvent is evaporated and the residue (27 g) is boiled in 100 ml butanol or 8 hours under reflux. Finally, the solvent is evaporated in a vacuum and the residue is purified by column chromatography over silica gel. 20 g 2-(2-chloroethyl)-5-methyl-1-phenylpyrazolin-3-one are obtained as an oil.

Workup

  1. temperatureThe reaction mixture is heated for 15 hours
  2. temperatureunder reflux
  3. customThe organic phase is separated off
  4. dry with materialdried over sodium sulphate
  5. filtrationfiltered
  6. customthe solvent is evaporated off under reduced pressure
  7. dissolutionThe residue is dissolved in ethyl ether
  8. filtrationthe solution is filtered
  9. customto remove the remaining initial material
  10. customThen the solvent is evaporated
  11. waitthe residue (27 g) is boiled in 100 ml butanol or 8 hours
  12. temperatureunder reflux
  13. customFinally, the solvent is evaporated in a vacuum
  14. customthe residue is purified by column chromatography over silica gel

Sources & evidence

ORD record
ord-69d56040f54845efbdf77cc12cda2c31
Source dataset
uspto-grants-1987_06
Patent number
US04672063

Reaction notes

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