Sodium Hydroxide → HCID 178442383, compound

HRID 848795Notes

Reaction equation

HRID 848795 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([Cl:24])=[C:6]([CH:23]=1)[NH:7][C:8]1[CH2:12][C:11](=[O:13])[N:10]([C:14]2[C:19]([Cl:20])=[CH:18][C:17]([Cl:21])=[CH:16][C:15]=2[Cl:22])[N:9]=1.Cl[CH:26]([CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37])[CH2:27][C:28](Cl)=[O:29].[OH-].[Na+]>C(#N)C.C1(C)C=CC=CC=1.[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC.O>[Cl:24][C:5]1[CH:4]=[CH:3][C:2]([N:1]2[CH:31]([CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37])[CH2:26][CH2:27][C:28]2=[O:29])=[CH:23][C:6]=1[NH:7][C:8]1[CH2:12][C:11](=[O:13])[N:10]([C:14]2[C:19]([Cl:20])=[CH:18][C:17]([Cl:21])=[CH:16][C:15]=2[Cl:22])[N:9]=1

Participants

8

Reactant 3

HCID 14798Sodium HydroxideHCID 20564669HCID 20564669, compoundHCID 178507595HCID 178507595, compound

Product 1

HCID 178442383HCID 178442383, compoundYield 81%

Reagents, catalysts & solvents 4

HCID 70681Tetrabutylammonium ChlorideCatalystHCID 962WaterSolvent2×HCID 1140TolueneSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

26 g of 3-(5-amino-2-chloroanilino)-1-(2,4,6-trichlorophenyl)-2-pyrazolin-5-one was suspended in 200 ml of acetonitrile and to the suspension 15.5 g of γ-chlorodecanoyl chloride described above was added dropwise under refluxing. After refluxing for 1 hour, the reaction mixture was cooled and water was added to the mixture followed by extracting with ethyl acetate. By distilling off the solvent under reduced pressure, the crystalline residue was obtained. The residue was dissolved in 300 ml of toluene; to the solution 3 g of tetrabutylammonium chloride was added, and then a solution containing 30 g of sodium hydroxide dissolved in 30 ml of water was added. After stirring vigorously at 60° C. for 4 hours, the reaction mixture was cooled and separated. The organic solvent layer was washed with water and the solvent was distilled off under reduced pressure. The residual crystals were recrystallized from acetonitrile to obtain 29 g of the desired compound. The melting point was 224° to 227° C.

Workup

  1. additionabove was added dropwise
  2. temperatureunder refluxing
  3. temperatureAfter refluxing for 1 hour
  4. temperaturethe reaction mixture was cooled
  5. extractionby extracting with ethyl acetate
  6. distillationBy distilling off the solvent under reduced pressure
  7. customthe crystalline residue was obtained
  8. additionwas added
  9. temperaturethe reaction mixture was cooled
  10. customseparated
  11. washThe organic solvent layer was washed with water
  12. distillationthe solvent was distilled off under reduced pressure
  13. customThe residual crystals were recrystallized from acetonitrile

Sources & evidence

ORD record
ord-4b070627aaa442cca1025d9f7d0fcc3e
Source dataset
uspto-grants-1981_10
Patent number
US04297440

Reaction notes

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