N-bromobutanimide → HCID 10177162, compound

HRID 1057372Notes

Reaction equation

HRID 1057372 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[NH:10][C:9]1=[O:21])=[O:7])([CH3:4])([CH3:3])[CH3:2].C1C(=O)N([Br:29])C(=O)C1>C(O)(=O)C.C(Cl)(Cl)Cl.C(Cl)Cl>[Br:29][C:16]1[C:17]([O:19][CH3:20])=[CH:18][C:11]2[NH:10][C:9](=[O:21])[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

6

Reactant 2

HCID 67184N-bromobutanimideHCID 9857210HCID 9857210, compound

Product 1

HCID 10177162HCID 10177162, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

A suspension of 3-tert-butoxycarbonyl-8-methoxy-2,3,4,5-tetrahydro-1H-1-benzazepine-2-one (1.00 g, 3.43 mmol) and NBS (0.672 g, 3.78 mmol) in acetic acid (0.8 mL) and chloroform (8 mL) was heated at reflux for 3 hrs. Then, the reaction mixture was diluted with DCM (30 mL), washed with water, dried over Na2SO4, filtered and evaporated. The crude residue was purified by flash chromatography on silica column using gradient elution with EtOAc/DCM (from 5% ethyl acetate in DCM to 10% ethyl acetate in DCM). The title compound was obtained as a white powder (0.689 g, 54%).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 3 hrs
  3. washwashed with water
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customevaporated
  7. customThe crude residue was purified by flash chromatography on silica column
  8. washelution with EtOAc/DCM (from 5% ethyl acetate in DCM to 10% ethyl acetate in DCM)

Sources & evidence

ORD record
ord-42866014304c4d729ddac88cb881817c
Source dataset
uspto-grants-2003_02
Patent number
US06514965B1

Reaction notes

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