Methacryloyl chloride → HCID 19032235, compound

HRID 1156390Notes

Reaction equation

HRID 1156390 reaction equation
[C:1]1([N:7]2[C:11](=[O:12])[CH:10]=[C:9]([NH2:13])[NH:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:14](Cl)(=[O:18])[C:15]([CH3:17])=[CH2:16]>N1C=CC=CC=1>[C:1]1([N:7]2[C:11](=[O:12])[CH:10]=[C:9]([NH:13][C:14](=[O:18])[C:15]([CH3:17])=[CH2:16])[NH:8]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 13528Methacryloyl chloride2×HCID 996833-Amino-1-phenyl-4,5-dihydropyrazolin-5-one2×

Product 1

HCID 19032235HCID 19032235, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Procedure

The 1-phenyl-3-methacrylamido-5-pyrazolone was prepared by acylation of 1-phenyl-3-amino-5-pyrazolone with an excess of methacrylyl chloride at 40° in pyridine by the following procedure. To a 500 ml three-necked flask fitted with a stirrer and thermometer there were added 35 g (0.2 mol) of 1-phenyl-3-amino-5-pyrazolone and 200 ml of dry pyridine. The mixture was stirred and the temperature held at 40° to 42°, and 42 g (0.4 mol) of methacrylyl chloride was added dropwise. After completion of the addition, the mixture was warmed to 75°. It was then poured onto cracked ice and allowed to stand overnight. The above-named product was filtered on a suction filter, washed with water and then recrystallized from ethanol. Coupler groups: 41 meq/100 g of polymeric coupler; carboxyl groups: 116 meq/100 g of polymeric coupler.

Workup

  1. customTo a 500 ml three-necked flask fitted with a stirrer
  2. customheld at 40° to 42°
  3. additionAfter completion of the addition
  4. temperaturethe mixture was warmed to 75°
  5. additionIt was then poured
  6. filtrationThe above-named product was filtered on a suction
  7. filtrationfilter
  8. washwashed with water
  9. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-13f05a58aafb440e909c3ce1045a14cc
Source dataset
uspto-grants-1982_06
Patent number
US04335197

Reaction notes

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