Methanol → HCID 20542689, compound

HRID 615028Notes

Reaction equation

HRID 615028 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:20])[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.[CH3:28]O.S(=O)(=O)(O)O>C(Cl)(Cl)(Cl)Cl>[CH3:28][O:20][C:19](=[O:21])[CH2:18][C:10]1[C:9]([C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)=[N:8][N:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[C:11]=1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 3084566Trifezolac

Product 1

HCID 20542689HCID 20542689, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

15 grams 1,3,5-triphenyl-pyrazol-4-acetic acid, 50 milliliters methanol, 40 milliliters carbon tetrachloride and 0.64 gram concentrated sulfuric acid were mixed and the mixture heated to the boiling temperature under reflux for 11 hours. The cooled reaction mixture was then extracted, first with sodium carbonate solution and thereafter with water. The organic phase was then dried and evaporated. The residue was recrystallized from a mixture of methanol and water. 14.2 grams 1,3,5-triphenyl-pyrazol-4-acetic acid-methyl ester, melting at 80.5°-81.5° C., were obtained, representing a yield of 91%.

Workup

  1. temperaturethe mixture heated to the boiling temperature
  2. temperatureunder reflux for 11 hours
  3. customThe cooled reaction mixture
  4. extractionwas then extracted, first with sodium carbonate solution
  5. customThe organic phase was then dried
  6. customevaporated
  7. customThe residue was recrystallized from a mixture of methanol and water

Sources & evidence

ORD record
ord-45641d9941ec4109899850c1b2379ffe
Source dataset
uspto-grants-1979_03
Patent number
US04146721

Reaction notes

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