Pyridine → HCID 13627551, compound

HRID 482856Notes

Reaction equation

HRID 482856 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:9]2[C:13](=[O:14])[CH2:12][C:11]([NH2:15])=[N:10]2)[CH:5]=[C:6]([Cl:8])[CH:7]=1.N1C=CC=CC=1.[N+](C1C=CC=CC=1)([O-])=O.[C:31](Cl)(=[O:34])[CH:32]=[CH2:33].[OH-].[Na+]>O.O1CCCC1>[Cl:1][C:2]1[CH:3]=[C:4]([N:9]2[C:13](=[O:14])[CH2:12][C:11]([NH:15][C:31](=[O:34])[CH:32]=[CH2:33])=[N:10]2)[CH:5]=[C:6]([Cl:8])[CH:7]=1

Participants

8

Reactant 5

HCID 1049PyridineHCID 7416NitrobenzeneHCID 13140Acryloyl chlorideHCID 14798Sodium HydroxideHCID 12799707HCID 12799707, compound

Product 1

HCID 13627551HCID 13627551, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

Fourteen-point-six grams (0.06 mole) of 1-(3,5-dichlorophenyl)-3-amino-2-pyrazoline-5-one, 11.4 ml (0.14 mole) of pyridine and 1.2 ml of nitrobenzene were added to 200 ml of tetrahydrofuran. To this mixture, cooled by ice, were added dropwise 12.7 g (0.14 mole) of acryloyl chloride. The liquid, after 30-minute stirring, was poured into 2 liters of water, extracted with use of ethyl acetate, and dried with use of anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure at a temperature of from 25° to 35° C. To the remaining oily substance were added 60 ml of ethanol and 60 ml of water, and further a solution of 8.4 g (0.21 mole) of sodium hydroxide dissolved in water. The liquid was stirred for 30 minutes at room temperature, and neutralized, and the thus deposited crystals were filtrated, and recrystallized from ethanol, whereby 8.6 g (48%) of Coupler Monomer (6) were obtained.

Workup

  1. temperatureTo this mixture, cooled by ice
  2. extractionextracted with use of ethyl acetate
  3. dry with materialdried with use of anhydrous sodium sulfate
  4. distillationthe solvent was distilled off under reduced pressure at a temperature of from 25° to 35° C
  5. additionTo the remaining oily substance were added 60 ml of ethanol and 60 ml of water
  6. stirringThe liquid was stirred for 30 minutes at room temperature
  7. filtrationneutralized, and the thus deposited crystals were filtrated
  8. customrecrystallized from ethanol, whereby 8.6 g (48%) of Coupler Monomer (6)
  9. customwere obtained

Sources & evidence

ORD record
ord-1f100f33bbcc4d99ad892de233fbe0da
Source dataset
uspto-grants-1986_03
Patent number
US04576911

Reaction notes

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