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

HRID 1281883Notes

Reaction equation

HRID 1281883 reaction equation
[C:1]([C:6]1[S:20][C:9]2[O:10][C:11]3[CH:19]=[CH:18][CH:17]=[CH:16][C:12]=3[NH:13][C:14](=[O:15])[C:8]=2[CH:7]=1)(=O)[CH2:2][CH2:3][CH3:4].C([SiH](CC)CC)C>FC(F)(F)C(O)=O>[CH2:1]([C:6]1[S:20][C:9]2[O:10][C:11]3[CH:19]=[CH:18][CH:17]=[CH:16][C:12]=3[NH:13][C:14](=[O:15])[C:8]=2[CH:7]=1)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 12052TriethylsilaneHCID 184223142-Butyrylthieno[2,3-b][1,5]benzoxazepin-4(5H)-one

Product 1

HCID 184222972-butylthieno[2,3-b][1,5]benzoxazepin-4(5H)-oneYield 57.3%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

2-Butyrylthieno[2,3-b][1,5]benzoxazepin-4(5H)-one (1.1 g) was dissolved in trifluoroacetic acid (20 ml) and triethylsilane (1.3 g) was added. The mixture was stirred at room temperature for 72 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-butylthieno[2,3-b][1,5]benzoxazepin-4(5H)-one (600 mg).

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-2738f8cbbc1745189eb6bebe526d814b
Source dataset
uspto-grants-2002_09
Patent number
US06455521B1

Reaction notes

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