3-Chloropropionyl chloride → 3-Chloro-1-(4-formyl-2,3,4,5-tetrahydro-1,4-benzoxazepin-7-yl)-1-propanone

HRID 429729Notes

Reaction equation

HRID 429729 reaction equation
[CH:1]([N:3]1[CH2:9][C:8]2[CH:10]=[CH:11][CH:12]=[CH:13][C:7]=2[O:6][CH2:5][CH2:4]1)=[O:2].[Cl:14][CH2:15][CH2:16][C:17](Cl)=[O:18].[Cl-].[Al+3].[Cl-].[Cl-]>ClCCCl>[Cl:14][CH2:15][CH2:16][C:17]([C:11]1[CH:12]=[CH:13][C:7]2[O:6][CH2:5][CH2:4][N:3]([CH:1]=[O:2])[CH2:9][C:8]=2[CH:10]=1)=[O:18]

Participants

5

Reactant 3

HCID 693643-Chloropropionyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 118195761,4-Benzoxazepine-4(5H)-carboxaldehyde, 2,3-dihydro-

Product 1

HCID 183526783-Chloro-1-(4-formyl-2,3,4,5-tetrahydro-1,4-benzoxazepin-7-yl)-1-propanoneYield 75.9%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a solution of 1.7 g of 4-formyl-2,3,4,5-tetrahydro-1,4-benzoxazepine and 1.28 g of 3-chloropropionyl chloride in 20 ml of 1,2-dichloroethane was added 3.0 g of aluminum chloride by portions. The mixture was stirred for 6 hours under reflux. The reaction mixture was poured into ice-water, and the resultant was subjected to extraction with dichloromethane. The extract was washed with water, dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by means of silica gel column chromatography (developing solvent: ethyl acetate) to give 1.95 g of the title compound as a colorless oily substance.

Workup

  1. temperatureunder reflux
  2. extractionthe resultant was subjected to extraction with dichloromethane
  3. washThe extract was washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationthe solvent was distilled off under reduced pressure
  6. customThe residue was purified by means of silica gel column chromatography (developing solvent: ethyl acetate)

Sources & evidence

ORD record
ord-048863db7e434cf49fc24558ed2b8f71
Source dataset
uspto-grants-2001_11
Patent number
US06319916B1

Reaction notes

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