N-bromobutanimide → HCID 58495360, compound

HRID 516219Notes

Reaction equation

HRID 516219 reaction equation
[NH2:1][C:2]1[CH:17]=[CH:16][C:5]2[CH2:6][CH2:7][N:8]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH2:9][CH2:10][C:4]=2[C:3]=1[Cl:18].[Br:19]N1C(=O)CCC1=O>ClCCl>[NH2:1][C:2]1[C:17]([Br:19])=[CH:16][C:5]2[CH2:6][CH2:7][N:8]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH2:9][CH2:10][C:4]=2[C:3]=1[Cl:18]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 58494705HCID 58494705, compound

Product 1

HCID 58495360HCID 58495360, compoundYield 77.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5.74 g of ethyl 7-amino-6-chloro-1,2,4,5-tetrahydro-3H-3-benzazepine-3-carboxylate in 100 ml of dichloromethane was added portionwise 3.9 g of N-bromosuccinimide under ice-cooling, followed by stirring for 40 minutes. The reaction mixture was concentrated under reduced pressure and the residue was purified by silica gel chromatography (elution solvent: HEX-EtOAc) to obtain 5.769 g of ethyl 7-amino-8-bromo-6-chloro-1,2,4,5-tetrahydro-3H-3-benzazepine-3-carboxylate as a brown solid.

Workup

  1. temperaturecooling
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customthe residue was purified by silica gel chromatography (elution solvent: HEX-EtOAc)

Sources & evidence

ORD record
ord-86cb805af9f343a392a7e9c16c3c01d9
Source dataset
uspto-grants-2015_08
Patent number
US09108977B2

Reaction notes

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