Ethanol → HCID 21162420, compound

HRID 894006Notes

Reaction equation

HRID 894006 reaction equation
[F:1][C:2]([F:25])([F:24])[C:3]1[CH:4]=[CH:5][C:6]2[S:12][C:11]3[CH:13]=[CH:14][C:15]([CH:17]([CH3:21])[C:18](N)=[O:19])=[CH:16][C:10]=3[C:9](=[O:22])[CH2:8][C:7]=2[CH:23]=1.C([OH:28])C.[OH-].[Na+]>O>[F:1][C:2]([F:25])([F:24])[C:3]1[CH:4]=[CH:5][C:6]2[S:12][C:11]3[CH:13]=[CH:14][C:15]([CH:17]([CH3:21])[C:18]([OH:28])=[O:19])=[CH:16][C:10]=3[C:9](=[O:22])[CH2:8][C:7]=2[CH:23]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 12895877HCID 12895877, compound

Product 1

HCID 21162420HCID 21162420, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
75 °C

Procedure

To a mixture of 40 mg of 2-(10,11-dihydro-8-trifluoromethyl-11-oxodibenzo[b,f]thiepin-2-yl)-propionamide and 1 ml of ethanol was added 200 mg of sodium hydroxide in 1 ml of water, and the mixture was stirred at 75° C. for 5 hours. After cooling, the solvent or ethanol was removed by distillation to obtain a residue, to which was added water, and the resulting mixture was washed with chloroform. The aqueous layer was acidified with hydrochloric acid and extracted with ethyl acetate. The extract was washed with a saturated sodium chloride solution and dried over anhydrous sodium sulfate. The solvent was distilled off to obtain a yellow oil, which was thin-layer chromatographed and developed with chloroform-methanol (10:1), thereby obtaining 15 mg (yield: 38%) of 2-(10,11-dihydro-8-trifluoromethyl-11-oxodibenzo[b,f]thiepin-2-yl)-propionic acid as a light yellow oil.

Workup

  1. temperatureAfter cooling
  2. customthe solvent or ethanol was removed by distillation
  3. customto obtain a residue
  4. washthe resulting mixture was washed with chloroform
  5. extractionextracted with ethyl acetate
  6. washThe extract was washed with a saturated sodium chloride solution
  7. dry with materialdried over anhydrous sodium sulfate
  8. distillationThe solvent was distilled off
  9. customto obtain a yellow oil, which
  10. customchromatographed

Sources & evidence

ORD record
ord-39dc6047fd2d4623ada27d84a6114a3d
Source dataset
uspto-grants-1981_08
Patent number
US04282245

Reaction notes

Loading…