Water → HCID 19962365, compound

HRID 53334Notes

Reaction equation

HRID 53334 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][CH2:12][CH2:13][C:14]2[CH:15]=[C:16]([CH2:29][CH2:30][C:31]([OH:33])=[O:32])[CH:17]=[C:18]([C:20](=[O:28])[C:21]3[CH:26]=[CH:25][C:24](F)=[CH:23][CH:22]=3)[CH:19]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[C:34](=O)([O-])[O-:35].[K+].[K+].O>CO>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][CH2:12][CH2:13][C:14]2[CH:15]=[C:16]([CH2:29][CH2:30][C:31]([OH:33])=[O:32])[CH:17]=[C:18]([C:20](=[O:28])[C:21]3[CH:26]=[CH:25][C:24]([O:35][CH3:34])=[CH:23][CH:22]=3)[CH:19]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 11430Potassium Carbonate2×HCID 199623683-[2-[(4-Chlorophenyl)sulphonylamino]ethyl]-5-(4-fluorobenzoyl)benzenepropanoic acid

Product 1

HCID 19962365HCID 19962365, compoundYield 85.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 3-[2-[(4-chlorophenyl)sulphonylamino]ethyl]-5-(4-fluorobenzoyl)benzenepropanoic acid (0.25 g) and potassium carbonate (0.212 g) in anhydrous methanol (5.0 ml) was heated under reflux for 18 hours. Additional potassium carbonate (0.212 g) was added and the mixture was heated under reflux for a further 20 hours and then cooled. Water (15 ml) was added and the solution was evaporated to about 10 ml and then acidified with 2N hydrochloric acid. The mixture was extracted several times with ethyl acetate and the combined extracts were washed with water and dried (MgSO4). Evaporation of the solvent gave the title compound as a glass (0.22 g). Found: C,60.25; H,4.92; N,2.51. C25H24ClNO6S requires C,59.81; H,4.82; N,2.79%.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 18 hours
  3. temperaturethe mixture was heated
  4. temperatureunder reflux for a further 20 hours
  5. temperaturecooled
  6. customthe solution was evaporated to about 10 ml
  7. extractionThe mixture was extracted several times with ethyl acetate
  8. washthe combined extracts were washed with water
  9. dry with materialdried (MgSO4)
  10. customEvaporation of the solvent

Sources & evidence

ORD record
ord-124031ecb21442b89a16ecd519315e68
Source dataset
uspto-grants-1997_04
Patent number
US05618941

Reaction notes

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