Pyridine → HCID 178454460, compound

HRID 1708852Notes

Reaction equation

HRID 1708852 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[C:4]([Cl:9])[C:3]=1[N:10]1[C:14](=[O:15])[CH:13]([C:16]2[CH:20]=[CH:19][NH:18][N:17]=2)[C:12]([NH:21][C:22](=[O:30])[C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([NH2:29])[CH:24]=2)=[N:11]1.N1C=CC=CC=1.[N+](C1C=CC=CC=1)([O-])=O.[C:46](Cl)(=[O:50])[C:47]([CH3:49])=[CH2:48].[OH-].[Na+]>O1CCCC1.O.C(O)(=O)C>[Cl:9][C:4]1[CH:5]=[C:6]([Cl:8])[CH:7]=[C:2]([Cl:1])[C:3]=1[N:10]1[C:14](=[O:15])[CH:13]([C:16]2[CH:20]=[CH:19][NH:18][N:17]=2)[C:12]([NH:21][C:22](=[O:30])[C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([NH:29][C:46](=[O:50])[C:47]([CH3:49])=[CH2:48])[CH:24]=2)=[N:11]1

Participants

9

Reactant 5

HCID 1049PyridineHCID 7416NitrobenzeneHCID 13528Methacryloyl chlorideHCID 14798Sodium HydroxideHCID 178507574HCID 178507574, compound

Product 1

HCID 178454460HCID 178454460, compoundYield 38.5%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

Next, 39.5 g (0.08 mol) of the 1-(2,4,6-trichlorophenyl)-3-(3-aminobenzamido)-4-pyrazolyl-5-oxo-2-pyrazoline was dissolved in 800 ml of tetrahydrofuran, and then 16 ml (0.2 mol) of pyridine and 2 ml of nitrobenzene were added. Next, 21 g (0.2 mol) of methacrylic acid chloride was added dropwise while cooling with ice, followed by stirring for 1.5 hours, after which 800 ml of water was added. Extraction with ethyl acetate was carried out. The extract was dried over anhydrous sodium sulfate, the solvent was distilled off under reduced pressure, and the residual oil was dissolved in 250 ml of ethanol. An aqueous solution of 4.8 g (0.12 mol) of sodium hydroxide in 100 ml of water was then added to the solution followed by stirring for 30 min, and then 5 ml of acetic acid was added and the separated oil was crystallized from acetonitrile. Its recrystallization from ethanol was made to obtain 16.4 g (38%) of the title compound. Melting point: 227° to 230° C.

Workup

  1. temperaturewhile cooling with ice
  2. extractionExtraction with ethyl acetate
  3. dry with materialThe extract was dried over anhydrous sodium sulfate
  4. distillationthe solvent was distilled off under reduced pressure
  5. dissolutionthe residual oil was dissolved in 250 ml of ethanol
  6. stirringby stirring for 30 min
  7. customthe separated oil was crystallized from acetonitrile
  8. customIts recrystallization from ethanol

Sources & evidence

ORD record
ord-07bde56ccfba4bb4a74a8982aada8f46
Source dataset
uspto-grants-1990_08
Patent number
US04946771

Reaction notes

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