Phosphorus oxychloride → 11-Chlorodibenzo[b,f][1,4]oxazepine

HRID 1907779Notes

Reaction equation

HRID 1907779 reaction equation
[CH:1]1[C:6]2[C:7](=O)[NH:8][C:9]3[CH:15]=[CH:14][CH:13]=[CH:12][C:10]=3[O:11][C:5]=2[CH:4]=[CH:3][CH:2]=1.P(Cl)(Cl)([Cl:19])=O>>[Cl:19][C:7]1=[N:8][C:9]2[CH:15]=[CH:14][CH:13]=[CH:12][C:10]=2[O:11][C:5]2[CH:4]=[CH:3][CH:2]=[CH:1][C:6]1=2

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 72374O-(o-Aminophenoxy)benzoic acid lactam

Product 1

HCID 706187211-Chlorodibenzo[b,f][1,4]oxazepineYield 86%

Procedure

A solution of 10,11-dihydrodibenz[b,f][1,4]oxazepin-11-one (1.00 g, 4.74 mmol) and phosphorus oxychloride (40 mL) was stirred for 5 h at reflux. The reaction mixture was then cooled to room temperature and concentrated under reduced pressure. The residue was dissolved into AcOEt and washed with water and brine. The organic layer was dried (Na2SO4), filtered and concentrated to give an orange oil. The residue was purified by silica gel column chromatography with EtOAc (10%) in hexanes to afford 554 (939 mg, 86%) as a yellow solid. LRMS (ESI): (calc) 229.0 (found) 230.1 (MH)+.

Workup

  1. temperatureat reflux
  2. concentrationconcentrated under reduced pressure
  3. dissolutionThe residue was dissolved into AcOEt
  4. washwashed with water and brine
  5. dry with materialThe organic layer was dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto give an orange oil
  9. customThe residue was purified by silica gel column chromatography with EtOAc (10%) in hexanes

Sources & evidence

ORD record
ord-925f4e3f221a456081800c2a2acb6b79
Source dataset
uspto-grants-2013_12
Patent number
US08598168B2

Reaction notes

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