Ethanol → HCID 20338088, compound

HRID 1395747Notes

Reaction equation

HRID 1395747 reaction equation
[O:1]=[C:2]1[CH2:8][C:7]2[CH:9]=[CH:10][CH:11]=[CH:12][C:6]=2[S:5][C:4]2[CH:13]=[C:14]([CH:17]([CH3:21])[C:18](N)=[O:19])[CH:15]=[CH:16][C:3]1=2.S(=O)(=O)(O)O.[CH2:27]([OH:29])[CH3:28]>>[O:1]=[C:2]1[CH2:8][C:7]2[CH:9]=[CH:10][CH:11]=[CH:12][C:6]=2[S:5][C:4]2[CH:13]=[C:14]([CH:17]([CH3:21])[C:18]([O:29][CH2:27][CH3:28])=[O:19])[CH:15]=[CH:16][C:3]1=2

Participants

4

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 20338077HCID 20338077, compound

Product 1

HCID 20338088HCID 20338088, compound

Procedure

To 300 mg of 2-(10,11-dihydro-11-oxo dibenzo[b,f]thiepin-3-yl)-propionamide in 3 ml of ethanol was added 0.3 ml of conc. sulfuric acid and the mixture was refluxed for 3.5 hours. The solvent was distilled off to obtain the residue, to which was added pieces of ice, and the mixture was extracted with ethyl acetate. The extract was washed with saturated sodium chloride solution and dried over anhydrous sodium sulfate. The solvent was distilled off to obtain brown oil, which was chromatographed over silica gel, eluted with chloroform, and there was obtained 277 mg of ethyl 2-(10,11-dihydro-11-oxo dibenzo[b,f]thiepin-3-yl)-propionate as pale brown oil.

Workup

  1. temperaturethe mixture was refluxed for 3.5 hours
  2. distillationThe solvent was distilled off
  3. customto obtain the residue
  4. additionto which was added pieces of ice
  5. extractionthe mixture was extracted with ethyl acetate
  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 brown oil, which
  10. customwas chromatographed over silica gel
  11. washeluted with chloroform

Sources & evidence

ORD record
ord-53b67106b4c6414b85caca03d449588d
Source dataset
uspto-grants-1980_05
Patent number
US04205170

Reaction notes

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