Phosphorus oxychloride → (E)-Methyl 11-chlorodibenzo[b,f][1,4]oxazepine-8-carboxylate

HRID 1907777Notes

Reaction equation

HRID 1907777 reaction equation
O=[C:2]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[O:6][C:5]2[CH:13]=[CH:14][C:15]([C:17]([O:19][CH3:20])=[O:18])=[CH:16][C:4]=2[NH:3]1.O=P(Cl)(Cl)[Cl:23]>>[Cl:23][C:2]1=[N:3][C:4]2[CH:16]=[C:15]([C:17]([O:19][CH3:20])=[O:18])[CH:14]=[CH:13][C:5]=2[O:6][C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]1=2

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 59737222Methyl 11-oxo-10,11-dihydrodibenzo[b,f][1,4]oxazepine-8-carboxylate

Product 1

HCID 58875660(E)-Methyl 11-chlorodibenzo[b,f][1,4]oxazepine-8-carboxylateYield 100%

Conditions

Temperature
100 °C

Procedure

Compound 548 (1.00 g, 3.71 mmol)) was suspended in POCl3 (20 mL). The reaction mixture was stirred at 100° C. for 3 h. POCl3 was removed on rotovap. The crude product was dissolved in ethyl acetate and washed with 2M Na2CO3 solution then with NaHCO3 saturated solution and finally with brine. The organic layer was separated and dried with Na2SO4, filtered and concentrated via rotary evaporation to afford compound 549 (1.069 g, 100%) as a orange solid that was taken on without further purification.

Workup

  1. customPOCl3 was removed on rotovap
  2. dissolutionThe crude product was dissolved in ethyl acetate
  3. washwashed with 2M Na2CO3 solution
  4. customThe organic layer was separated
  5. dry with materialdried with Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated via rotary evaporation

Sources & evidence

ORD record
ord-185d9d493deb44baac8f63ab34c284a5
Source dataset
uspto-grants-2013_12
Patent number
US08598168B2

Reaction notes

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