N-bromobutanimide → HCID 23298010, compound

HRID 1422210Notes

Reaction equation

HRID 1422210 reaction equation
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([N:6]=[C:7]([O:14][CH3:15])[C:8]([O:12][CH3:13])=[N:9]2)=[C:4]([CH3:16])[CH:3]=1.[Br:17]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([N:6]=[C:7]([O:14][CH3:15])[C:8]([O:12][CH3:13])=[N:9]2)=[C:4]([CH2:16][Br:17])[CH:3]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 232980507-Bromo-2,3-dimethoxy-5-methylquinoxaline

Product 1

HCID 23298010HCID 23298010, compound

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

15 g (53 mmol) of 7-bromo-5-methyl-2,3-dimethoxy-quinoxaline, 9.9 g (1.05 equiv.) of N-bromosuccinimide and 0.87 g (0.1 equiv.) of azo-isobutyronitrile are dissolved in 100 ml of carbon tetrachloride and the solution is stirred at reflux for 24 hours. The solid is filtered off and the filtrate is diluted with dichloromethane, then washed once with each of water and brine. The organic phase is dried over magnesium sulfate and concentrated by evaporation. The residue is recrystallized from ethyl acetate and hexane. The title compound is obtained in the form of light-orange crystals.

Workup

  1. temperatureat reflux for 24 hours
  2. filtrationThe solid is filtered off
  3. additionthe filtrate is diluted with dichloromethane
  4. washwashed once with each of water and brine
  5. dry with materialThe organic phase is dried over magnesium sulfate
  6. concentrationconcentrated by evaporation
  7. customThe residue is recrystallized from ethyl acetate and hexane

Sources & evidence

ORD record
ord-94c68e858ea046f886de8dc83e034cfe
Source dataset
uspto-grants-2000_06
Patent number
US06080743

Reaction notes

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