Sodium Hydroxide → 5-(4-methoxyphenyl)-4-phenyl-4H-1,2,4-triazole-3-acetic acid

HRID 4599Notes

Reaction equation

HRID 4599 reaction equation
C([O:3][C:4](=[O:25])[CH2:5][C:6]1[N:10]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:9]([C:17]2[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=2)=[N:8][N:7]=1)C.[OH-].[Na+]>C(O)C>[CH3:24][O:23][C:20]1[CH:19]=[CH:18][C:17]([C:9]2[N:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[C:6]([CH2:5][C:4]([OH:25])=[O:3])=[N:7][N:8]=2)=[CH:22][CH:21]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 13174853HCID 13174853, compound

Product 1

HCID 201515485-(4-methoxyphenyl)-4-phenyl-4H-1,2,4-triazole-3-acetic acidYield 98.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 4 g of the product of Example 16, 10 ml of 2N sodium hydroxide and 20 ml of ethanol was stirred at 60° C. under argon for 30 minutes and the ethanol was evaporated at 40° C. under reduced pressure. 9.9 ml of 2N hydrochloric acid were added to the aqueous solution and the mixture stood at 0° to 5° C. for 16 hours and was filtered. The recovered product was cmpasted several times with ice water to remove chlorides and was dried at room temperature under reduced pressure of 0.5 to 1 mmHg to obtain 3.6 g of 5-(4-methoxyphenyl)-4-phenyl-4H-1,2,4-triazole-3-acetic acid.

Workup

  1. customthe ethanol was evaporated at 40° C. under reduced pressure
  2. addition9.9 ml of 2N hydrochloric acid were added to the aqueous solution
  3. waitthe mixture stood at 0° to 5° C. for 16 hours
  4. filtrationwas filtered
  5. customto remove chlorides
  6. customwas dried at room temperature under reduced pressure of 0.5 to 1 mmHg

Sources & evidence

ORD record
ord-1fd7cbb8125345dca119b87a84a21449
Source dataset
uspto-grants-1988_02
Patent number
US04727084

Reaction notes

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