Pyridine → HCID 13627549, compound

HRID 482854Notes

Reaction equation

HRID 482854 reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[N:9]1[C:13](=[O:14])[CH2:12][C:11]([NH2:15])=[N:10]1.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[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[N:9]1[C:13](=[O:14])[CH2:12][C:11]([NH:15][C:31](=[O:35])[C:32]([CH3:34])=[CH2:33])=[N:10]1

Participants

9

Reactant 5

HCID 1049PyridineHCID 7416NitrobenzeneHCID 13528Methacryloyl chlorideHCID 14798Sodium HydroxideHCID 13627548HCID 13627548, compound

Product 1

HCID 13627549HCID 13627549, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Forty grams (0.16 mole) of 1-(2,3-dichlorophenyl)-3-amino-2-pyrazoline-5-one, 30.4 ml (0.38 mole) of pyridine, and 4.0 ml of nitrobenzene were added to 600 ml of tetrahydrofuran, and to the mixture, cooled by ice, were added dropwise 39.2 g (0.38 mole) of methacryloyl chloride, and the liquid was stirred for 30 minutes, and then poured into 4 liters of water, extracted with use of ethyl acetate, then 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 80 ml of ethanol and 80 ml of water and then a solution containing 22.4 g (0.56 mole) of sodium hydroxide. This mixture was stirred for 30 minutes at room temperature, and neutralized with acetic acid. The deposited crystals were filtrated, and recrystallized from methanol, whereby 32.4 g (64%) of Coupler Monomer (1 ) were obtained.

Workup

  1. temperatureto the 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 80 ml of ethanol and 80 ml of water
  6. stirringThis mixture was stirred for 30 minutes at room temperature
  7. filtrationThe deposited crystals were filtrated
  8. customrecrystallized from methanol, whereby 32.4 g (64%) of Coupler Monomer (1 )
  9. customwere obtained

Sources & evidence

ORD record
ord-b1140796fa8b4283ab4d56aa38b350ff
Source dataset
uspto-grants-1986_03
Patent number
US04576911

Reaction notes

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