Sodium Hydroxide → HCID 19085310, compound

HRID 963107Notes

Reaction equation

HRID 963107 reaction equation
[OH-].[Na+].[Cl:3][C:4]1[CH:38]=[CH:37][CH:36]=[CH:35][C:5]=1[C:6]([C:8]1[CH:12]=[C:11]([CH2:13][CH3:14])[S:10][C:9]=1[N:15]1[C:19]([CH3:20])=[N:18][N:17]=[C:16]1[CH2:21][NH:22][C:23]([C:25]1[CH:26]=[C:27]([CH:32]=[CH:33][CH:34]=1)[C:28]([O:30]C)=[O:29])=[O:24])=[O:7]>CO>[Cl:3][C:4]1[CH:38]=[CH:37][CH:36]=[CH:35][C:5]=1[C:6]([C:8]1[CH:12]=[C:11]([CH2:13][CH3:14])[S:10][C:9]=1[N:15]1[C:19]([CH3:20])=[N:18][N:17]=[C:16]1[CH2:21][NH:22][C:23]([C:25]1[CH:26]=[C:27]([CH:32]=[CH:33][CH:34]=1)[C:28]([OH:30])=[O:29])=[O:24])=[O:7]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 19085225HCID 19085225, compound

Product 1

HCID 19085310HCID 19085310, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methanol (13 ml) and a 2M sodium hydroxide aqueous solution (2.5 ml) were added to methyl 3-(4-(3-(2-chlorobenzoyl)-5-ethylthiophen-2-yl)-5-methyl[1,2,4]triazol-3-ylmethylcarbamoyl)benzoate (1.3 g), and the mixture was stirred at room temperature for 2 hours. The reaction mixture was evaporated, and the residue was partitioned between water and ethyl acetate. The aqueous layer was taken out, and citric acid was added to adjust the aqueous solution to pH 3. The solution was extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over magnesium sulfate. The solvent was evaporated, and the residue was recrystallized from a mixed solvent of ethyl acetate and diisopropyl ether to give 1.05 g of 3-(4-(3-(2-chlorobenzoyl)-5-ethylthiophen-2-yl)-5-methyl[1,2,4]triazol-3-ylmethylcarbamoyl)benzoic acid.

Workup

  1. customThe reaction mixture was evaporated
  2. customthe residue was partitioned between water and ethyl acetate
  3. additioncitric acid was added
  4. extractionThe solution was extracted with ethyl acetate
  5. washThe organic layer was washed with saturated brine
  6. dry with materialdried over magnesium sulfate
  7. customThe solvent was evaporated
  8. customthe residue was recrystallized from a mixed solvent of ethyl acetate and diisopropyl ether

Sources & evidence

ORD record
ord-18072c035f57436a84a00adee72d0386
Source dataset
uspto-grants-1998_06
Patent number
US05760032

Reaction notes

Loading…