N-bromobutanimide → HCID 9856670, compound

HRID 1057369Notes

Reaction equation

HRID 1057369 reaction equation
[CH3:1][O:2][C:3]1[CH:14]=[CH:13][C:6]2[CH2:7][CH2:8][CH2:9][C:10](=[O:12])[NH:11][C:5]=2[CH:4]=1.C1C(=O)N([Br:22])C(=O)C1>C(Cl)(Cl)(Cl)Cl.C(Cl)Cl>[Br:22][C:14]1[C:3]([O:2][CH3:1])=[CH:4][C:5]2[NH:11][C:10](=[O:12])[CH2:9][CH2:8][CH2:7][C:6]=2[CH:13]=1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 6769538-methoxy-2,3,4,5-tetrahydro-1H-1-benzazepin-2-one

Product 1

HCID 9856670HCID 9856670, compound

Reagents, catalysts & solvents 2

HCID 5943Carbon TetrachlorideSolventHCID 6344DichloromethaneSolvent

Procedure

A suspension of 8-methoxy-2,3,4,5-tetrahydro-1H-1-benzazepine-2-one (100 mg, 0.52 mmol), NBS (103 mg, 0.57 mmol) and BPO (ca. 5 mg) in carbon tetrachloride (1.5 mL) was heated at reflux for 3 hrs. The reaction mixture was allowed to cool to room temperature, diluted with DCM (20 mL), washed with water and dried over Na2SO4. Filtration and evaporation of the organic layer provided a solid residue, which was washed with n-hexane and dried in high vacuum. The title compound was obtained as a white crystalline product (140 mg, 100%).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 3 hrs
  3. washwashed with water
  4. dry with materialdried over Na2SO4
  5. filtrationFiltration and evaporation of the organic layer
  6. customprovided a solid residue, which
  7. washwas washed with n-hexane
  8. customdried in high vacuum

Sources & evidence

ORD record
ord-c01a03e1a9044f7f99c5af604018ad7c
Source dataset
uspto-grants-2003_02
Patent number
US06514965B1

Reaction notes

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