Acetonitrile → HCID 19860054, compound

HRID 2072661Notes

Reaction equation

HRID 2072661 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:12]([NH:16][C:17]2[CH:22]=[C:21]([NH2:23])[CH:20]=[CH:19][C:18]=2[Cl:24])[NH:11]1.C(#N)C.[C:28]([C:36]1[CH:46]=[CH:45][C:39]([O:40][CH2:41][C:42](Cl)=[O:43])=[CH:38][CH:37]=1)([CH2:31][C:32]([CH3:35])([CH3:34])[CH3:33])([CH3:30])[CH3:29]>N1C=CC=CC=1>[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:12]([NH:16][C:17]2[CH:22]=[C:21]([NH:23][C:42](=[O:43])[CH2:41][O:40][C:39]3[CH:45]=[CH:46][C:36]([C:28]([CH2:31][C:32]([CH3:35])([CH3:34])[CH3:33])([CH3:29])[CH3:30])=[CH:37][CH:38]=3)[CH:20]=[CH:19][C:18]=2[Cl:24])[NH:11]1

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 11030961-(2',4',6'-Trichlorophenyl)-3-(2'-chloro-5'-aminoanilino)-5-pyrazoloneHCID 19926029HCID 19926029, compound

Product 1

HCID 19860054HCID 19860054, compoundYield 854.2%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Forty point four grams of 1-(2,4,6-trichlorophenyl)-3-(2-chloro-5-aminoanilino)-5-pyrazolone were dissolved into 250 ml of acetonitrile, and to the solution were added 9.4 grams of pyridine. To this mixture, while being refluxed by heating, were dropwise added 28.3 g of 4-t-octylphenoxyacetyl chloride, and the reflux was further continued for another hour. The acetonitrile was distilled off from the reaction liquid under reduced pressure, then 500 ml of water and ethyl acetate were added to the liquid, and then the reaction product was extracted by ethyl acetate. The residuum that has been obtained by distilling off the ethyl acetate phase under reduced pressure was recrystallized from 300 ml of ethanol, whereby 55 g of objective 1-(2,4,6-trichlorophenyl)-3-[2-chloro-5-(4-t-octylphenoxyacetamido)anilino]-5-pyrazolone were obtained. Melting point: 126° to 128° C. The structure was confirmed through the procedures of NMR, IR and MASS.

Workup

  1. temperatureTo this mixture, while being refluxed
  2. temperatureby heating
  3. waitthe reflux was further continued for another hour
  4. distillationThe acetonitrile was distilled off from the reaction liquid under reduced pressure
  5. addition500 ml of water and ethyl acetate were added to the liquid
  6. extractionthe reaction product was extracted by ethyl acetate
  7. customThe residuum that has been obtained
  8. distillationby distilling off the ethyl acetate phase under reduced pressure
  9. customwas recrystallized from 300 ml of ethanol

Sources & evidence

ORD record
ord-f7f543b63db140ab99c22839dabee68d
Source dataset
uspto-grants-1990_04
Patent number
US04914013

Reaction notes

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