Acetic Acid → HCID 53990084, compound

HRID 2285968Notes

Reaction equation

HRID 2285968 reaction equation
[CH2:1]([O:3][C:4](=[O:25])[CH2:5][CH:6]([C:16](=O)[C:17]1[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=1)[C:7](=O)[C:8]1[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][CH:9]=1)[CH3:2].[C:26]1([NH:32][NH2:33])[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.C(O)(=O)C>C1C=CC=CC=1>[CH2:1]([O:3][C:4](=[O:25])[CH2:5][C:6]1[C:16]([C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=2)=[N:33][N:32]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:7]=1[C:8]1[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][CH:9]=1)[CH3:2]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 7516PhenylhydrazineHCID 53970847HCID 53970847, compound

Product 1

HCID 53990084HCID 53990084, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

12.0 grams 3,3-bis-(p-chlorobenzoyl)-propionic acid ethyl ester, 3.9 grams phenylhydrazine and 2.7 grams glacial acetic acid were mixed and the mixture was heated in a nitrogen atmosphere to the boiling temperature under reflux for 6 hours. To the reaction mixture were than added benzene, and the pH was adjusted to 2-3, followed by extraction with water. The benzene was evaporated from the benzene phase and the dry, crystalline residue was recrystallized from a mixture of cyclohexane and petroleum ether boiling in a range from 50°-70° C. 13.0 grams 1-phenyl-3,5-bis-(p-chlorophenyl)-pyrazol-4-acetic acid ethyl ester, melting at 120°-122° C., were obtained, representing a yield of 91%.

Workup

  1. temperaturethe mixture was heated in a nitrogen atmosphere to the boiling temperature
  2. temperatureunder reflux for 6 hours
  3. extractionfollowed by extraction with water
  4. customThe benzene was evaporated from the benzene phase
  5. customthe dry, crystalline residue was recrystallized from a mixture of cyclohexane and petroleum ether boiling in a range from 50°-70° C

Sources & evidence

ORD record
ord-258311d56a4e4deaa9eddda7ad062c9f
Source dataset
uspto-grants-1982_04
Patent number
US04325962

Reaction notes

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