Ammonia → HCID 53905449, compound

HRID 615030Notes

Reaction equation

HRID 615030 reaction equation
[C:1]1([N:7]2[C:11]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[C:10]([CH2:18][C:19]([OH:21])=O)[C:9]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[N:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.P(Cl)(Cl)(Cl)=O.[NH3:33].O>C1C=CC=CC=1.C(OC(=O)C)C>[C:1]1([N:7]2[C:11]([C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=3)=[C:10]([CH2:18][C:19]([NH2:33])=[O:21])[C:9]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[N:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 4

HCID 222AmmoniaHCID 962WaterHCID 24813Phosphorus oxychlorideHCID 3084566Trifezolac

Product 1

HCID 53905449HCID 53905449, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

3.54 grams 1,3,5-triphenyl-pyrazol-4-acetic acid, 1.68 gram phosphorus oxychloride and 30 milliliters benzene were mixed and the mixture heated to the boiling temperature under reflux for 2 hours. The reaction mixture, containing in benzene solution the correspondingly substituted acetyl chloride was then added dropwise at 0° C. to 30 milliliters 25% aqueous ammonia solution. The mixture was permitted to stand over night at room temperature. Thereafter, 30 milliliteres water and enough ethylacetate were added to cause dissolution of the crystalline mass formed in the reaction mixture. The organic phase was separated, dried with magnesium sulfate, evaporated and the residue was recrystallized from a mixture of ethanol and water. 3.2 grams 1,3,5-triphenyl-pyrazol-4-acetamide, melting at 207°-207.5° C., were obtained, representing a yield of 91%.

Workup

  1. temperaturethe mixture heated to the boiling temperature
  2. temperatureunder reflux for 2 hours
  3. waitto stand over night at room temperature
  4. dissolutiondissolution of the crystalline mass
  5. customformed in the reaction mixture
  6. customThe organic phase was separated
  7. dry with materialdried with magnesium sulfate
  8. customevaporated
  9. customthe residue was recrystallized from a mixture of ethanol and water

Sources & evidence

ORD record
ord-c4a2a6a6ad30403490c7999334599f15
Source dataset
uspto-grants-1979_03
Patent number
US04146721

Reaction notes

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