Triethylsilane → 2-ethylthieno[2,3-b][1,5]benzoxazepin-4(5H)-one

HRID 1281881Notes

Reaction equation

HRID 1281881 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].C([SiH](CC)CC)C>FC(F)(F)C(O)=O>[CH2:1]([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)[CH3:2]

Participants

4

Reactant 2

HCID 12052TriethylsilaneHCID 184223372-acetylthieno[2,3-b][1,5]benzoxazepin-4(5H)-one

Product 1

HCID 184222472-ethylthieno[2,3-b][1,5]benzoxazepin-4(5H)-oneYield 77.5%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

2-Acetylthieno[2,3-b][1,5]benzoxazepin-4(5H)-one (1.5 g) was dissolved in trifluoroacetic acid (20 ml) and triethylsilane (2 g) was added. The mixture was stirred at room temperature for 42 hours. The solvent was evaporated under reduced pressure and the residue was dissolved in chloroform. The mixture was washed with water and saturated aqueous sodium hydrogencarbonate solution, and dried over sodium sulfate. The solvent was evaporated under reduced pressure. To the residue were added chloroform and ethyl acetate and the precipitated crystals were collected by filtration. The obtained crystals were washed with diisopropyl ether to give 2-ethylthieno[2,3-b][1,5]benzoxazepin-4(5H)-one (1.1 g).

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. dissolutionthe residue was dissolved in chloroform
  3. washThe mixture was washed with water and saturated aqueous sodium hydrogencarbonate solution
  4. dry with materialdried over sodium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. additionTo the residue were added chloroform and ethyl acetate
  7. filtrationthe precipitated crystals were collected by filtration
  8. washThe obtained crystals were washed with diisopropyl ether

Sources & evidence

ORD record
ord-8e08805920ce4fd0a7d70d115b45261b
Source dataset
uspto-grants-2002_09
Patent number
US06455521B1

Reaction notes

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