Potassium Hydroxide → HCID 20506969, compound

HRID 1395760Notes

Reaction equation

HRID 1395760 reaction equation
[O:1]=[C:2]1[CH2:8][C:7]2[CH:9]=[CH:10][CH:11]=[N:12][C:6]=2[S:5][C:4]2[CH:13]=[CH:14][C:15]([CH:17]([CH3:21])[C:18](N)=[O:19])=[CH:16][C:3]1=2.[OH-:22].[K+].[OH-].[Na+]>C(OCC)C.O.C(O)C>[O:1]=[C:2]1[CH2:8][C:7]2[CH:9]=[CH:10][CH:11]=[N:12][C:6]=2[S:5][C:4]2[CH:13]=[CH:14][C:15]([CH:17]([CH3:21])[C:18]([OH:22])=[O:19])=[CH:16][C:3]1=2

Participants

7

Reactant 3

HCID 14797Potassium HydroxideHCID 14798Sodium HydroxideHCID 20338043HCID 20338043, compound

Product 1

HCID 20506969HCID 20506969, compoundYield 81.9%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolvent2×HCID 3283Diethyl EtherSolvent

Procedure

To 101 mg of 2-(5,6-dihydro-6-oxo benzo[b]pyrido[3,2-f]-thiepin-8-yl)-propionamide were added 0.4 g of potassium hydroxide, 1 ml of water and 4 ml of ethanol and the mixture was refluxed with stirring for 5 hours. After cooling, to this were added water and 3% sodium hydroxide solution, then a small amount of diethyl ether, and the mixture was shaked. The aqueous layer was collected and acidified with acetic acid, and to this was added sodium chloride, and the resulting mixture was extracted with chloroform. The extract was washed with saturated sodium chloride solution and dried over anhydrous sodium sulfate. The solvent was distilled off to obtain 115 mg of brown glutinous substance, which was chromatographed over silica gel, eluted with chloroform/methanol(100/1-20/1), and there was obtained 83 mg of 2-(5,6-dihydro-6-oxo benzo[b]pyrido[3,2-f]thiepin-8-yl)-propionic acid as colorless glutinous substance. This was solidified by washing with n-hexane and there was obtained colorless crystals having a melting point of 141°-143° C.

Workup

  1. temperaturethe mixture was refluxed
  2. temperatureAfter cooling
  3. customThe aqueous layer was collected
  4. additionto this was added sodium chloride
  5. extractionthe resulting mixture was extracted with chloroform
  6. washThe extract was washed with saturated sodium chloride solution
  7. dry with materialdried over anhydrous sodium sulfate
  8. distillationThe solvent was distilled off
  9. customto obtain 115 mg of brown glutinous substance, which
  10. customwas chromatographed over silica gel
  11. washeluted with chloroform/methanol(100/1-20/1)

Sources & evidence

ORD record
ord-cabb018962af482c90630e9a977d85c6
Source dataset
uspto-grants-1980_05
Patent number
US04205170

Reaction notes

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