Bromine → HCID 22105470, compound

HRID 1456638Notes

Reaction equation

HRID 1456638 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:11][C:10](=[O:12])[CH2:9][CH:8]=[C:7]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[Cl:19])[C:6]=2[CH:20]=1.[Br:21]Br>C(Cl)(Cl)(Cl)Cl>[Br:21][CH:9]1[CH:8]=[C:7]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[Cl:19])[C:6]2[CH:20]=[C:2]([Cl:1])[CH:3]=[CH:4][C:5]=2[NH:11][C:10]1=[O:12]

Participants

4

Reactant 2

HCID 24408BromineHCID 22105467HCID 22105467, compound

Product 1

HCID 22105470HCID 22105470, compoundYield 65.3%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A suspension of 0.78 g (2.56 mmole) of 7-chloro-5-(2-chlorophenyl)-1,3-dihydro-2H-1-benzazepin-2-one in 100 mL of carbon tetrachloride was heated to reflux, yielding a clear solution. Bromine (0.19 mL, 3.69 mmole) was added in one portion and the solution was, heated at reflux, under a sunlamp, for 15 minutes. Without cooling, the reaction solution was washed with 5% aqueous sodium thiosulfate and water, dried (sodium sulfate), and concentrated. The residue was triturated with ether. The solid was collected on a filter, washed with ether and dried yielding 0.64 g (65%) of the title compound. This crude material (shown by NMR to have a ratio of product to starting material of 85:15) was used as is in the next step.

Workup

  1. temperaturewas heated
  2. temperatureto reflux
  3. customyielding a clear solution
  4. temperatureheated
  5. temperatureat reflux, under a sunlamp, for 15 minutes
  6. temperatureWithout cooling
  7. washthe reaction solution was washed with 5% aqueous sodium thiosulfate and water
  8. dry with materialdried (sodium sulfate)
  9. concentrationconcentrated
  10. customThe residue was triturated with ether
  11. customThe solid was collected on a filter
  12. washwashed with ether
  13. customdried

Sources & evidence

ORD record
ord-53b8f6bbca1244dfb46cb171cd26728e
Source dataset
uspto-grants-1998_12
Patent number
US05843941

Reaction notes

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