N-bromobutanimide → 3-bromodihydro-1-[(4-methoxyphenyl)methyl]-1H-azepine-2,4(3H,5H)-dione

HRID 1529565Notes

Reaction equation

HRID 1529565 reaction equation
[Br:1]N1C(=O)CCC1=O.[CH3:9][O:10][C:11]1[CH:26]=[CH:25][C:14]([CH2:15][N:16]2[CH2:22][CH2:21][CH2:20][C:19](=[O:23])[CH2:18][C:17]2=[O:24])=[CH:13][CH:12]=1.OS([O-])(=O)=O.[Na+].O>C1COCC1>[Br:1][CH:18]1[C:19](=[O:23])[CH2:20][CH2:21][CH2:22][N:16]([CH2:15][C:14]2[CH:13]=[CH:12][C:11]([O:10][CH3:9])=[CH:26][CH:25]=2)[C:17]1=[O:24]

Participants

5

Reactant 3

HCID 67184N-bromobutanimideHCID 23673662Sodium bisulfate monohydrateHCID 66609054N-(p-methoxybenzyl)azepane-2,4-dione

Product 1

HCID 666132613-bromodihydro-1-[(4-methoxyphenyl)methyl]-1H-azepine-2,4(3H,5H)-dioneYield 151.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

N-Bromosuccinimide (2.88 g, 16.17 mmol) was added portionwise to a stirred solution of 1-(4-methoxy-benzyl)-azepane-2,4-dione (4.0 g, 16.17 mmol) and NaHSO4.H2O (0.67 g, 4.85 mmol) in THF anhydrous (80 mL) at 0° C. The reaction mixture was stirred at room temperature for 2.5 hours and the solvent evaporated in vacuo to yield 3-bromodihydro-1-[(4-methoxyphenyl)methyl]-1H-azepine-2,4(3H,5H)-dione (8 g, 91% yield, 60% pure) as a viscous orange oil which was used in the next step without further purification.

Workup

  1. customthe solvent evaporated in vacuo

Sources & evidence

ORD record
ord-4d99d66eacda4db18120c4551c2842c2
Source dataset
uspto-grants-2015_07
Patent number
US09090632B2

Reaction notes

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