Sodium Hydroxide → HCID 9819646, compound

HRID 2393634Notes

Reaction equation

HRID 2393634 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]([F:31])=[CH:27][CH:26]=2)=[C:16](\[CH2:22][CH2:23][OH:24])/[C:17]([O:19]CC)=O)=[CH:11][CH:10]=1)(=[O:8])=[O:7])(C)(C)C.[OH-].[Na+]>C(O)C.O>[NH2:5][S:6]([C:9]1[CH:10]=[CH:11][C:12](/[C:15](=[C:16]2/[C:17](=[O:19])[O:24][CH2:23][CH2:22]/2)/[C:25]2[CH:26]=[CH:27][C:28]([F:31])=[CH:29][CH:30]=2)=[CH:13][CH:14]=1)(=[O:8])=[O:7]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 70223253HCID 70223253, compound

Product 1

HCID 9819646HCID 9819646, compoundYield 77.6%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

Ethyl (E)-3-(4-t-butylaminosulfonylphenyl)-3-(4-fluorophenyl)-2-(2-hydroxyethyl)-2-propenoate (10 g), prepared in Example 59, is dissolved in 20 ml of ethanol, and a solution of 2 g of sodium hydroxide in 10 ml of water is added. The mixture is refluxed for 2 h. After evaporation to dryness, the residue is taken up with water, acidified with 1N hydrochloric acid and then extracted with dichloromethane. The organic phase is dried over magnesium sulphate and then evaporated under vacuum. The residue is added in portions to 500 ml of concentrated sulphuric acid. The mixture is stirred for 15 minutes at room temperature and then poured into iced water and the crystals formed are filtered off, washed with diethyl ether and then taken up with 100 ml of warm acetone. 50 ml of diethyl ether are added to the solution obtained and the crystals formed are filtered off and dried to give 6 g of (E)-3-[1-(4-aminosulphonylphenyl)-1-(4-fluorophenyl)methylidene]dihydrofuran-2-one in the form of crystals melting at 202° C.

Workup

  1. temperatureThe mixture is refluxed for 2 h
  2. customAfter evaporation to dryness
  3. extractionextracted with dichloromethane
  4. dry with materialThe organic phase is dried over magnesium sulphate
  5. customevaporated under vacuum
  6. additionThe residue is added in portions to 500 ml of concentrated sulphuric acid
  7. additionpoured into iced water
  8. customthe crystals formed
  9. filtrationare filtered off
  10. washwashed with diethyl ether
  11. addition50 ml of diethyl ether are added to the solution
  12. customobtained
  13. customthe crystals formed
  14. filtrationare filtered off
  15. customdried

Sources & evidence

ORD record
ord-52fe3bd53c9e4bbaba7a3da809845e8e
Source dataset
uspto-grants-1998_09
Patent number
US05807873

Reaction notes

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