Butyryl chloride → 2-butylthieno[2,3-b][1,5]benzoxazepin-4(5H)-one

HRID 650004Notes

Reaction equation

HRID 650004 reaction equation
[S:1]1[C:5]2[O:6][C:7]3[CH:15]=[CH:14][CH:13]=[CH:12][C:8]=3[NH:9][C:10](=[O:11])[C:4]=2[CH:3]=[CH:2]1.[C:16](Cl)(=O)[CH2:17][CH2:18][CH3:19].[Cl-].[Al+3].[Cl-].[Cl-]>ClCCCl>[CH2:16]([C:2]1[S:1][C:5]2[O:6][C:7]3[CH:15]=[CH:14][CH:13]=[CH:12][C:8]=3[NH:9][C:10](=[O:11])[C:4]=2[CH:3]=1)[CH2:17][CH2:18][CH3:19]

Participants

5

Reactant 3

HCID 8855Butyryl chlorideHCID 6451240Aluminum(III) ChlorideHCID 18422172HCID 18422172, compound

Product 1

HCID 184222972-butylthieno[2,3-b][1,5]benzoxazepin-4(5H)-oneYield 63.6%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

Thieno[2,3-b][1,5]benzoxazepin-4(5H)-one (1.5 g) was suspended in 1,2-dichloroethane (20 ml) and butyryl chloride (880 mg) was added. To this reaction system was added portionwise aluminium chloride (4.6 g) under ice-cooling. The mixture was stirred at room temperature for 45 minutes. Insoluble matter was filtrated and the filtrate was poured into ice water, and chloroform was added. The organic layer was washed with water and dried over sodium sulfate. The solvent was evaporated under reduced pressure and water-ethanol was added. The precipitated crystals were collected by filtration. The obtained crystals were washed with chloroform-diisopropyl ether to give 2-butylthieno[2,3-b][1,5]benzoxazepin-4(5H)-one (1.2 g).

Workup

  1. temperaturecooling
  2. filtrationInsoluble matter was filtrated
  3. additionthe filtrate was poured into ice water, and chloroform
  4. additionwas added
  5. washThe organic layer was washed with water
  6. dry with materialdried over sodium sulfate
  7. customThe solvent was evaporated under reduced pressure and water-ethanol
  8. additionwas added
  9. filtrationThe precipitated crystals were collected by filtration
  10. washThe obtained crystals were washed with chloroform-diisopropyl ether

Sources & evidence

ORD record
ord-d9a696ea63cf4e42b81a65cdd85aa3ef
Source dataset
uspto-grants-2001_08
Patent number
US06271225B1

Reaction notes

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