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

HRID 718029Notes

Reaction equation

HRID 718029 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 1 (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-1289525490584608b7bba4eb62d2e1cb
Source dataset
uspto-grants-2015_11
Patent number
US09193749B2

Reaction notes

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