4-Toluenesulfonyl chloride → 5,11-Dihydro-5-[2-(4-methylphenylsulfonyl)oxyethyl]dibenzo [b,e][1,4]oxazepine

HRID 1859468Notes

Reaction equation

HRID 1859468 reaction equation
[OH:1][CH2:2][CH2:3][N:4]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[CH2:8][O:7][C:6]2[CH:15]=[CH:16][CH:17]=[CH:18][C:5]1=2.[C:19]1([CH3:29])[CH:24]=[CH:23][C:22]([S:25](Cl)(=[O:27])=[O:26])=[CH:21][CH:20]=1>N1C=CC=CC=1>[CH3:29][C:19]1[CH:24]=[CH:23][C:22]([S:25]([O:1][CH2:2][CH2:3][N:4]2[C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=3[CH2:8][O:7][C:6]3[CH:15]=[CH:16][CH:17]=[CH:18][C:5]2=3)(=[O:27])=[O:26])=[CH:21][CH:20]=1

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 186256285,11-Dihydro-5-(2-hydroxyethyl) dibenzo[b,e][1,4]oxazepine

Product 1

HCID 186255895,11-Dihydro-5-[2-(4-methylphenylsulfonyl)oxyethyl]dibenzo [b,e][1,4]oxazepine

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

0.99 g (4.1 mmol) of 5,11-dihydro-5-(2-hydroxyethyl) dibenzo[b,e][1,4]oxazepine was dissolved in 6 ml of anhydrous pyridine. 0.94 g (4.9 mmol) of p-toluenesulfonyl chloride was added to the obtained solution, and they were stirred at room temperature for 6 hours. The solvent was evaporated under reduced pressure. The residue was dissolved in dichloromethane. The obtained solution was washed with 5% aqueous potassium hydrogensulfate solution, saturated aqueous sodium hydrogencarbonate solution and saturated aqueous sodium chloride solution successively. After drying, the solvent was evaporated under reduced pressure. The obtained residue was subjected to silica gel column chromatography. The product was eluted with ethyl acetate and hexane (1:3). The appropriate fractions were combined, and the solvent was evaporated under reduced pressure to obtain 5,11-dihydro-5-[2-(4-methylphenylsulfonyl)oxyethyl]dibenzo[b,e][1,4]oxazepine in the form of a light yellow oil (1.25 g, 76.6%).

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. dissolutionThe residue was dissolved in dichloromethane
  3. washThe obtained solution was washed with 5% aqueous potassium hydrogensulfate solution, saturated aqueous sodium hydrogencarbonate solution and saturated aqueous sodium chloride solution successively
  4. customAfter drying
  5. customthe solvent was evaporated under reduced pressure
  6. washThe product was eluted with ethyl acetate and hexane (1:3)
  7. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-178e2dde3f36480ea8e7e858ee7c992b
Source dataset
uspto-grants-2003_03
Patent number
US06528504B2

Reaction notes

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