N-bromobutanimide → HCID 20464796, compound

HRID 325416Notes

Reaction equation

HRID 325416 reaction equation
[CH2:1]([O:3][C:4](=[O:19])[C:5](=[O:18])[C:6]1[N:7]([CH3:17])[C:8]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[C:9]([CH3:11])[CH:10]=1)[CH3:2].[Br:20]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[Br:20][CH2:11][C:9]1[CH:10]=[C:6]([C:5](=[O:18])[C:4]([O:3][CH2:1][CH3:2])=[O:19])[N:7]([CH3:17])[C:8]=1[C:12]([O:14][CH2:15][CH3:16])=[O:13]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 20464711HCID 20464711, compound

Product 1

HCID 20464796HCID 20464796, compound

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

Ethyl-1,4-dimethyl-5-ethoxycarbonyl-α-oxopyrrole-2-acetate (14.79 g, 55.5 mmol) is dissolved in carbon tetrachloride (300 ml) and placed in a 500 ml round bottom flask. Then N-bromosuccinimide (11.1 g, 62.5 mmol) is added, a reflux condenser is attached and the system is flushed with nitrogen. The mixture is slowly stirred. A 120 V, 150 W G.E. projection lamp is placed against the side of the flask and the lamp and the flask are enclosed in aluminum foil. The reaction mixture is then irradiated for one hour. The lamp is then removed, the solution is cooled and the succinimide is filtered off. The solvent is removed to give a yellow oil which solidifies. This material is then used immediately in the next reaction (vide infra).

Workup

  1. customplaced in a 500 ml round bottom flask
  2. customa reflux condenser is attached
  3. customthe system is flushed with nitrogen
  4. customprojection lamp is placed against the side of the flask
  5. customThe reaction mixture is then irradiated for one hour
  6. customThe lamp is then removed
  7. temperaturethe solution is cooled
  8. filtrationthe succinimide is filtered off
  9. customThe solvent is removed
  10. customto give a yellow oil which
  11. customThis material is then used immediately in the next reaction (vide infra)

Sources & evidence

ORD record
ord-ecb41f130f794e61a8fe2cd6a6845d65
Source dataset
uspto-grants-1984_04
Patent number
US04440779

Reaction notes

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