HCID 131720828, compound → HCID 9907063, compound

HRID 568078Notes

Reaction equation

HRID 568078 reaction equation
C([NH:5][S:6]([C:9]1[CH:14]=[CH:13][C:12](/[C:15](/[C:25]2[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][CH:26]=2)=[C:16](\[CH2:22]CO)/[C:17]([O:19][CH2:20]C)=[O:18])=[CH:11][CH:10]=1)(=[O:8])=[O:7])(C)(C)C>FC(F)(F)C(O)=O>[Cl:31][C:28]1[CH:27]=[CH:26][C:25](/[C:15](=[C:16]2\[C:17](=[O:18])[O:19][CH2:20][CH2:22]\2)/[C:12]2[CH:11]=[CH:10][C:9]([S:6]([NH2:5])(=[O:7])=[O:8])=[CH:14][CH:13]=2)=[CH:30][CH:29]=1

Participants

3

Reactant 1

HCID 131720828HCID 131720828, compound

Product 1

HCID 9907063HCID 9907063, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 10 g of ethyl (Z)-3-(4-t-butylaminosulphonylphenyl)-3-(4-chlorophenyl)-2-(2-hydroxyethyl)-2-propenoate prepared in Example 124, in 80 ml of trifluoroacetic acid is heated under reflux for 15 hours. After evaporation of the solvent under vacuum, the residue is taken up in dichloromethane. The organic phase is washed with water and then dried over magnesium sulphate and evaporated under vacuum to give an oil which crystallises in an acetone/diisopropyl ether mixture giving 3.9 g of (Z)-4-[(4-chlorophenyl)-(2-oxo-dihydro-furan-3-ylidene)-methyl]benzenesulphonamide in the form of crystals melting at 187-189° C.

Workup

  1. temperatureunder reflux for 15 hours
  2. customAfter evaporation of the solvent under vacuum
  3. washThe organic phase is washed with water
  4. dry with materialdried over magnesium sulphate
  5. customevaporated under vacuum
  6. customto give an oil which
  7. customcrystallises in an acetone/diisopropyl ether mixture

Sources & evidence

ORD record
ord-aae5a317838e4db494ccde079db40126
Source dataset
uspto-grants-2001_01
Patent number
US06180651B2

Reaction notes

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