Pyridine → HCID 13627550, compound

HRID 482855Notes

Reaction equation

HRID 482855 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]=[CH:6][C:7]=1[Cl:8].N1C=CC=CC=1.[N+](C1C=CC=CC=1)([O-])=O.[C:31](Cl)(=[O:35])[C:32]([CH3:34])=[CH2:33].[OH-].[Na+]>C(O)(=O)C.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:35])[C:32]([CH3:34])=[CH2:33])=[N:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

9

Reactant 5

HCID 1049PyridineHCID 7416NitrobenzeneHCID 13528Methacryloyl chlorideHCID 14798Sodium HydroxideHCID 12799708HCID 12799708, compound

Product 1

HCID 13627550HCID 13627550, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

Twenty grams (0.08 mole) of 1-(3,4-dichlorophenyl)-3-amino-2-pyrazoline-5-one, 15.2 ml (0.19 mole) of pyridine and 2.0 ml of nitrobenzene were added to 300 ml of tetrahydrofuran. To this mixture, cooled by ice, were added dropwise 19.6 g (0.19 mole) of methacryloyl 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 11.2 g (0.28 mole) of sodium hydroxide dissolved into water. This mixture was stirred for 30 minutes at room temperature, and neutralized with acetic acid. The thus deposited crystals were filtrated, and recrystallized from ethanol, whereby 14.4 g (57%) of Coupler Monomer (3) were obtained. M.P. 212°-213° C.

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. stirringThis mixture was stirred for 30 minutes at room temperature
  7. filtrationThe thus deposited crystals were filtrated
  8. customrecrystallized from ethanol, whereby 14.4 g (57%) of Coupler Monomer (3)
  9. customwere obtained

Sources & evidence

ORD record
ord-51f2d4070ab6414f8d09f0d3d5473333
Source dataset
uspto-grants-1986_03
Patent number
US04576911

Reaction notes

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