Sodium Carbonate → HCID 20542669, compound

HRID 615029Notes

Reaction equation

HRID 615029 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.P(Cl)(Cl)(Cl)=O.[C:33](=[O:36])([O-])[O-:34].[Na+].[Na+]>C1C=CC=CC=1>[C:33]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[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)([OH:34])=[O:36]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 24813Phosphorus oxychlorideHCID 3084566Trifezolac

Product 1

HCID 20542669HCID 20542669, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

7.0 grams 1,3,5-triphenyl-pyrazol-4-acetic acid, 3.1 grams phosphorus oxychloride and 40 milliliters benzene were mixed and the mixture was heated to the boiling temperature under reflux for 2 hours. The reaction mixture was then poured on ice, the pH adjusted to 6 by the addition of dilute aqueous sodium carbonate solution. The benzene solution was separated, washed with water, dried over anhydrous magnesium sulfate, and evaporated. The residue, consisting of 1,3,5-triphenyl-pyrazol-4-acetylchloride was taken up in 40 milliliters absolute ether. The ether solution was then added dropwise at 0°-3° C. and within 20 minutes to a solution of 2.8 grams salicyclic acid in a mixture of 20 milliliters ether and 4.2 grams pyridine. The mixture was after stirred for 25 minutes and thereafter poured on a mixture of ice and concentrated aqueous hydrochloric acid. The acid solution was separated, extracted with water, and the ether evaporated. The residue was recrystallized from ethanol. 5.1 grams 1,3,5-triphenyl-pyrazol-4-acetic acid-(2-carboxyphenyl)-ester, melting at 190°-191° C., were obtained representing a yield of 54%.

Workup

  1. temperaturethe mixture was heated to the boiling temperature
  2. temperatureunder reflux for 2 hours
  3. additionThe reaction mixture was then poured on ice
  4. customThe benzene solution was separated
  5. washwashed with water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customevaporated
  8. additionThe ether solution was then added dropwise at 0°-3° C. and within 20 minutes to a solution of 2.8 grams salicyclic acid in a mixture of 20 milliliters ether and 4.2 grams pyridine
  9. additionpoured on a mixture of ice and concentrated aqueous hydrochloric acid
  10. customThe acid solution was separated
  11. extractionextracted with water
  12. customthe ether evaporated
  13. customThe residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-8f917a27d76b4a75ad92130b1823f7ec
Source dataset
uspto-grants-1979_03
Patent number
US04146721

Reaction notes

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