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

HRID 1281878Notes

Reaction equation

HRID 1281878 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:19])[CH2:17][CH3:18].[Cl-].[Al+3].[Cl-].[Cl-]>ClCCCl>[C: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)(=[O:19])[CH2:17][CH3:18]

Participants

5

Reactant 3

HCID 62324Propionyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 18422172Thieno[2,3-b][1,5]benzoxazepin-4(5H)-one

Product 1

HCID 184222072-propionylthieno[2,3-b][1,5]benzoxazepin-4(5H)-oneYield 74.2%

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 propionyl chloride (770 mg) was added. To this reaction system was added portionwise aluminum chloride (4.7 g) under ice-cooling. Insoluble matter was filtrated, and the filtrate was poured into ice water and chloroform was added. The aqueous layer was extracted twice with chloroform and the combined organic layer was dried over sodium sulfate. The solvent was evaporated under reduced pressure and the precipitated crystals were collected by filtration to give 2-propionylthieno[2,3-b][1,5]benzoxazepin-4(5H)-one (1.4 g).

Workup

  1. temperaturecooling
  2. filtrationInsoluble matter was filtrated
  3. additionthe filtrate was poured into ice water and chloroform
  4. additionwas added
  5. extractionThe aqueous layer was extracted twice with chloroform
  6. dry with materialthe combined organic layer was dried over sodium sulfate
  7. customThe solvent was evaporated under reduced pressure
  8. filtrationthe precipitated crystals were collected by filtration

Sources & evidence

ORD record
ord-fe6efc1e841c472aab1ae5c9bf8f747b
Source dataset
uspto-grants-2002_09
Patent number
US06455521B1

Reaction notes

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