Phosphorus pentachloride → 8,11-Dichlorodibenzo[b,f][1,4]oxazepine

HRID 1450190Notes

Reaction equation

HRID 1450190 reaction equation
[Cl:1][C:2]1[CH:17]=[CH:16][C:5]2[O:6][C:7]3[CH:15]=[CH:14][CH:13]=[CH:12][C:8]=3[C:9](=O)[NH:10][C:4]=2[CH:3]=1.P(Cl)(Cl)(Cl)(Cl)[Cl:19]>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:17]=[CH:16][C:5]2[O:6][C:7]3[CH:15]=[CH:14][CH:13]=[CH:12][C:8]=3[C:9]([Cl:19])=[N:10][C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 24819Phosphorus pentachlorideHCID 766192-Chlorodibenz(b,f)-1,4-oxazepin-11(10H)-one

Product 1

HCID 189404158,11-Dichlorodibenzo[b,f][1,4]oxazepineYield 89.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a stirred solution of 8-chloro-10, 11-dihydrodibenz[b,f][1,4]oxazepin-11-one (0.53 g, 2.15 mmol) in toluene (20 mL) was added phosphorus pentachloride (0.54 g, 2.58 mmol) at room temperature under argon. The resulting mixture was heated at reflux for 4 h and the solvent was removed in vacuo. The residue was redissolved in toluene and reconcentrated. The light yellow solid (0.51 g, quantitative yield) was used directly for the next reaction without further purification.

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureat reflux for 4 h
  3. customthe solvent was removed in vacuo
  4. dissolutionThe residue was redissolved in toluene

Sources & evidence

ORD record
ord-4cdaaa1c114f4cecb0ae4a8c8ac6a26d
Source dataset
uspto-grants-1997_02
Patent number
US05602121

Reaction notes

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