Hydrochloric Acid → 2-isopropenylthieno[2,3-b][1,5]benzoxazepin-4(5H)-one

HRID 650009Notes

Reaction equation

HRID 650009 reaction equation
[C:1]([C:4]1[S:18][C:7]2[O:8][C:9]3[CH:17]=[CH:16][CH:15]=[CH:14][C:10]=3[NH:11][C:12](=[O:13])[C:6]=2[CH:5]=1)(=O)[CH3:2].[CH3:19]I.[Mg].Cl>CCOCC>[C:1]([C:4]1[S:18][C:7]2[O:8][C:9]3[CH:17]=[CH:16][CH:15]=[CH:14][C:10]=3[NH:11][C:12](=[O:13])[C:6]=2[CH:5]=1)([CH3:19])=[CH2:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 184223372-acetylthieno[2,3-b][1,5]benzoxazepin-4(5H)-oneHCID 86584867HCID 86584867, compound

Product 1

HCID 184222742-isopropenylthieno[2,3-b][1,5]benzoxazepin-4(5H)-one

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

2-Acetylthieno[2,3-b][1,5]benzoxazepin-4(5H)-one (1.8 g) was suspended in ether (15 ml) and 20 equivalent amounts of magnesium methyl iodide was added under ice-cooling. The mixture was stirred at room temperature for 24 hours. The reaction mixture was poured into 1M hydrochloric acid under ice-cooling and insoluble matter was filtered off. The resulting mixture was extracted twice with chloroform. The chloroform layer was dried over sodium sulfate and the solvent was evaporated under reduced pressure. The residue was suspended in toluene and a catalytic amount of p-toluenesulfonic acid was added. The mixture was stirred under reflux with heating for 20 minutes. The reaction system was cooled to room temperature and the reaction mixture was washed with saturated aqueous sodium hydrogencarbonate solution. The solvent was evaporated under reduced pressure and diisopropyl ether was added to the residue. The precipitated crystals were collected by filtration to give 2-isopropenylthieno[2,3-b][1,5]benzoxazepin-4(5H)-one (800 mg).

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. filtrationinsoluble matter was filtered off
  4. extractionThe resulting mixture was extracted twice with chloroform
  5. dry with materialThe chloroform layer was dried over sodium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. additiona catalytic amount of p-toluenesulfonic acid was added
  8. stirringThe mixture was stirred
  9. temperatureunder reflux
  10. temperaturewith heating for 20 minutes
  11. temperatureThe reaction system was cooled to room temperature
  12. washthe reaction mixture was washed with saturated aqueous sodium hydrogencarbonate solution
  13. customThe solvent was evaporated under reduced pressure and diisopropyl ether
  14. additionwas added to the residue
  15. filtrationThe precipitated crystals were collected by filtration

Sources & evidence

ORD record
ord-61d4620c77cf439b80f233876d6d4ccd
Source dataset
uspto-grants-2001_08
Patent number
US06271225B1

Reaction notes

Loading…