Benzyl Bromide → 10-Benzyl-11-oxo-10,11-dihydrodibenzo[b,f][1,4]oxazepine-8-carbaldehyde

HRID 638856Notes

Reaction equation

HRID 638856 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH2:7](Br)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[O:15]=[C:16]1[C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=2[O:20][C:19]2[CH:27]=[CH:28][C:29]([CH:31]=[O:32])=[CH:30][C:18]=2[NH:17]1>C(#N)C.C(OCC)(=O)C>[CH2:7]([N:17]1[C:16](=[O:15])[C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=2[O:20][C:19]2[CH:27]=[CH:28][C:29]([CH:31]=[O:32])=[CH:30][C:18]1=2)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 2222445211-Oxo-10,11-dihydrodibenzo[b,f][1,4]oxazepine-8-carbaldehyde

Product 1

HCID 2222449110-Benzyl-11-oxo-10,11-dihydrodibenzo[b,f][1,4]oxazepine-8-carbaldehydeYield 63%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

Potassium carbonate anhydrous (0.207 g, 1.5 mmole) and benzyl bromide (0.205 g, 1.2 mmole) were added to a solution of the 11-oxo-10,11dihydrodibenzo[b,f][1,4]oxazepine-8-carbaldehyde (0.240 g, 1 mmole) in acetonitrile under N2 at room temperature. The reaction mixture then was refluxed for 4 hours, and cooled to room temperature. Diluted the reaction mixture with ethyl acetate and filtered through a magnesol pad and concentrated. Purified with silica gel column and 50% ethyl acetate in hexane. Obtained the desired compound (light yellow oil) in 63% yield.

Workup

  1. temperatureThe reaction mixture then was refluxed for 4 hours
  2. filtrationfiltered through a magnesol pad
  3. concentrationconcentrated
  4. customPurified with silica gel column and 50% ethyl acetate in hexane

Sources & evidence

ORD record
ord-45c2c30d8e374b47a224293bd4da9036
Source dataset
uspto-grants-2010_04
Patent number
US07691842B2

Reaction notes

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