N-bromobutanimide → HCID 10111450, compound

HRID 1057365Notes

Reaction equation

HRID 1057365 reaction equation
[C:1]([O:5][C:6]([CH:8]1[CH2:14][CH2:13][C:12]2[CH:15]=[CH:16][C:17]([O:19][CH3:20])=[CH:18][C:11]=2[N:10]([CH2:21][CH3:22])[C:9]1=[O:23])=[O:7])([CH3:4])([CH3:3])[CH3:2].[Br:24]N1C(=O)CCC1=O>C(O)(=O)C.C(Cl)(Cl)Cl>[Br:24][C:16]1[C:17]([O:19][CH3:20])=[CH:18][C:11]2[N:10]([CH2:21][CH3:22])[C:9](=[O:23])[CH:8]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH2:14][CH2:13][C:12]=2[CH:15]=1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 9836705HCID 9836705, compound

Product 1

HCID 10111450HCID 10111450, compoundYield 77.1%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6212ChloroformSolvent2×

Procedure

A solution of 3(R,S)-tert-butoxycarbonyl-1-ethyl-8-methoxy-2,3,4,5-tetrahydro-1H-1-benzazepine-2-one (3.38 g, 10.58 mmol) and N-bromosuccinimide (2.072 g, 11.64 mmol) in acetic acid (2.5 mL) and chloroform (25 mL) was heated at reflux for 2 hrs. The reaction mixture was diluted with chloroform (25 mL), washed with saturated aqueous solution of NaHCO3 and water, dried over Na2SO4, filtered and evaporated to dryness. Purification of the crude product by flash chromatography on silica gel column eluted with EtOAc/hexane (3:7) provided the desired compound (3.25 g, 77%) as white powder.

Workup

  1. temperatureat reflux for 2 hrs
  2. washwashed with saturated aqueous solution of NaHCO3 and water
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customevaporated to dryness
  6. customPurification of the crude product by flash chromatography on silica gel column
  7. washeluted with EtOAc/hexane (3:7)

Sources & evidence

ORD record
ord-9ff92b5fb11645a1b202ff43242e84a0
Source dataset
uspto-grants-2003_02
Patent number
US06514965B1

Reaction notes

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