Water → 1-[2-ethoxy-4-[(ethylamino)carbonyl]phenyl]-1H-1,2,3-Triazole-4-carboxylic acid

HRID 1717332Notes

Reaction equation

HRID 1717332 reaction equation
[CH2:1]([O:3][C:4]1[CH:9]=[C:8]([C:10]([NH:12][CH2:13][CH3:14])=[O:11])[CH:7]=[CH:6][C:5]=1[N:15]1[CH:19]=[C:18]([C:20]([O:22]CC)=[O:21])[N:17]=[N:16]1)[CH3:2].[OH-].[Na+].O>C(O)C>[CH2:1]([O:3][C:4]1[CH:9]=[C:8]([C:10]([NH:12][CH2:13][CH3:14])=[O:11])[CH:7]=[CH:6][C:5]=1[N:15]1[CH:19]=[C:18]([C:20]([OH:22])=[O:21])[N:17]=[N:16]1)[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 68516073ethyl 1-{2-ethoxy-4-[(ethylamino)carbonyl]phenyl}-1H-1,2,3-triazole-4-carboxylate

Product 1

HCID 685156141-[2-ethoxy-4-[(ethylamino)carbonyl]phenyl]-1H-1,2,3-Triazole-4-carboxylic acidYield 77.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a solution of ethyl 1-{2-ethoxy-4-[(ethylamino)carbonyl]phenyl}-1H-1,2,3-triazole-4-carboxylate (0.51 g) obtained in Example 131e) in ethanol (8 ml) was added 8N aqueous sodium hydroxide solution (0.39 ml), and the mixture was stirred at room temperature for 5 hr. Water was added to the reaction mixture, and ethanol was evaporated under reduced pressure. Water was added to the obtained aqueous solution and the mixture was washed with ethyl acetate. 1N Hydrochloric acid was added to acidify the aqueous solution. The deposited precipitate was collected by filtration, washed with water and air-dried to give the title compound as a white powder (0.36 g, 76%).

Workup

  1. customwas evaporated under reduced pressure
  2. additionWater was added to the obtained aqueous solution
  3. washthe mixture was washed with ethyl acetate
  4. addition1N Hydrochloric acid was added
  5. filtrationThe deposited precipitate was collected by filtration
  6. washwashed with water
  7. customair-dried

Sources & evidence

ORD record
ord-ad996ebaa3164c459bba85c107a38987
Source dataset
uspto-grants-2010_09
Patent number
US07803822B2

Reaction notes

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