Ethanol → HCID 20338053, compound

HRID 1395755Notes

Reaction equation

HRID 1395755 reaction equation
[O:1]=[C:2]1[CH2:8][C:7]2[CH:9]=[CH:10][CH:11]=[CH:12][C:6]=2[O: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[O: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 20338042HCID 20338042, compound

Product 1

HCID 20338053HCID 20338053, compound

Procedure

To 50 mg of 2-(10,11-dihydro-11-oxo dibenzo[b,f]oxepin-3-yl)-propionamide in 2 ml of ethanol was added 0.2 ml of conc. sulfuric acid and the mixture was refluxed with stirring for 5 hours. The solvent was distilled off to obtain the residue, which 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 yellow oil, which was chromatographed over silica gel, eluted with chloroform and there was obtained 55 mg of ethyl 2-(10,11-dihydro-11-oxo dibenzo[b,f]oxepin-3-yl)-propionate as pale yellow oil.

Workup

  1. temperaturethe mixture was refluxed
  2. distillationThe solvent was distilled off
  3. customto obtain the residue, which
  4. extractionwas extracted with ethyl acetate
  5. washThe extract was washed with saturated sodium chloride solution
  6. dry with materialdried over anhydrous sodium sulfate
  7. distillationThe solvent was distilled off
  8. customto obtain yellow oil, which
  9. customwas chromatographed over silica gel
  10. washeluted with chloroform

Sources & evidence

ORD record
ord-4bcfc74a426846d9819afa0a4f6e2c4b
Source dataset
uspto-grants-1980_05
Patent number
US04205170

Reaction notes

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