Sodium Hydroxide → HCID 67727833, compound

HRID 963042Notes

Reaction equation

HRID 963042 reaction equation
[Cl:1][C:2]1[CH:40]=[CH:39][CH:38]=[CH:37][C:3]=1[C:4]([C:6]1[CH:10]=[C:9]([CH2:11][CH3:12])[S:8][C:7]=1[N:13]1[C:17]([CH2:18][CH2:19][C:20]([O:22]CC)=[O:21])=[N:16][N:15]=[C:14]1[CH2:25][NH:26][C:27](=[O:36])[C:28]1[CH:33]=[CH:32][C:31]([Cl:34])=[C:30]([Cl:35])[CH:29]=1)=[O:5].[OH-].[Na+]>CO>[Cl:1][C:2]1[CH:40]=[CH:39][CH:38]=[CH:37][C:3]=1[C:4]([C:6]1[CH:10]=[C:9]([CH2:11][CH3:12])[S:8][C:7]=1[N:13]1[C:17]([CH2:18][CH2:19][C:20]([OH:22])=[O:21])=[N:16][N:15]=[C:14]1[CH2:25][NH:26][C:27](=[O:36])[C:28]1[CH:33]=[CH:32][C:31]([Cl:34])=[C:30]([Cl:35])[CH:29]=1)=[O:5]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67727746HCID 67727746, compound

Product 1

HCID 67727833HCID 67727833, compoundYield 83.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

Ethyl 3-(4-(3-(2-chlorobenzoyl)-5-ethylthiophen-2-yl)-3-(3,4-dichlorobenzoylaminomethyl) [1,2,4]triazol-5-yl)propionate (0.7 g) and a 2M aqueous sodium hydroxide solution (1.13 ml) were added to methanol (10 ml), and the mixture was stirred at 50° C. for 3 hours. The solvent was evaporated, and the residue was dissolved in water. Ethyl acetate was added to the solution for washing. The aqueous layer was taken out, and citric acid was added to adjust the solution to pH 3. The solution was extracted with ethyl acetate. The extract was washed with saturated brine and dried over magnesium sulfate. The solvent was evaporated, and the residue was recrystallized from diisopropyl ether to give 0.56 g of 3-(4-(3-(2-chlorobenzoyl)-5-ethylthiophen-2-yl)-3-(3,4-dichlorobenzoylaminomethyl) [1,2,4]triazol-5-yl)propionic acid.

Workup

  1. customThe solvent was evaporated
  2. dissolutionthe residue was dissolved in water
  3. additionEthyl acetate was added to the solution
  4. washfor washing
  5. additioncitric acid was added
  6. extractionThe solution was extracted with ethyl acetate
  7. washThe extract was washed with saturated brine
  8. dry with materialdried over magnesium sulfate
  9. customThe solvent was evaporated
  10. customthe residue was recrystallized from diisopropyl ether

Sources & evidence

ORD record
ord-198b2fc2bc334cabb702d63592a6a859
Source dataset
uspto-grants-1998_06
Patent number
US05760032

Reaction notes

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