N-bromobutanimide → HCID 67148260, compound

HRID 2219053Notes

Reaction equation

HRID 2219053 reaction equation
[C:1]([O:9][C:10]1[C:20](=[O:21])[N:14]2[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][C:13]2=[N:12][C:11]=1[C:22]([O:24][CH3:25])=[O:23])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br:26]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[C:1]([O:9][C:10]1[C:20](=[O:21])[N:14]2[CH2:15][CH2:16][CH2:17][CH2:18][CH:19]([Br:26])[C:13]2=[N:12][C:11]=1[C:22]([O:24][CH3:25])=[O:23])(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 67147764HCID 67147764, compound

Product 1

HCID 67148260HCID 67148260, compound

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of methyl 3-(benzoyloxy)-4-oxo-4,6,7,8,9,10-hexahydropyrimido[1,2-a]azepine-2-carboxylate, N-bromo-succinimide (2 eq.) and α,α′-azoisobutyronitrile (0.45 eq.) in carbon tetrachloride was stirred under reflux for 14 hour. The mixture was cooled to room temperature, the succinimide was filtered off and the solvent was removed under reduced pressure. Methyl 3-(benzoyloxy)-10-bromo-4-oxo-4,6,7,8,9,10-hexahydropyrimido[1,2-a]azepine-2-carboxylate was obtained after flash chromatography (eluents petroleum ether/ethyl acetate, 8:2) as a pale yellow solid.

Workup

  1. temperatureunder reflux for 14 hour
  2. filtrationthe succinimide was filtered off
  3. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-8e25f124c51d45db97221a8361f9e441
Source dataset
uspto-grants-2008_08
Patent number
US07414045B2

Reaction notes

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