N-bromobutanimide → HCID 22614890, compound

HRID 842680Notes

Reaction equation

HRID 842680 reaction equation
[Br:1]N1C(=O)CCC1=O.[Cl:9][C:10]1[C:11]([N:25]2[CH:29]=[N:28][N:27]=[C:26]2[C:30]2[CH:31]=[N:32][CH:33]=[CH:34][CH:35]=2)=[C:12]2[C:17](=[CH:18][C:19]=1[Cl:20])[N:16]=[C:15]([O:21][CH3:22])[C:14]([O:23][CH3:24])=[N:13]2>ClC(Cl)(Cl)C>[Cl:9][C:10]1[C:11]([N:25]2[C:29]([Br:1])=[N:28][N:27]=[C:26]2[C:30]2[CH:31]=[N:32][CH:33]=[CH:34][CH:35]=2)=[C:12]2[C:17](=[CH:18][C:19]=1[Cl:20])[N:16]=[C:15]([O:21][CH3:22])[C:14]([O:23][CH3:24])=[N:13]2

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 22614854HCID 22614854, compound

Product 1

HCID 22614890HCID 22614890, compoundYield 72.2%

Reagents, catalysts & solvents 1

HCID 62781,1,1-TrichloroethaneSolvent

Procedure

N-Bromosuccinimide (58 mg, 0.33 mmol) was added to a stirred suspension of 6,7-dichloro-2,3-dimethoxy-5-[3-(3-pyridyl)-4H-1,2,4-triazol-4-yl]quinoxaline (Preparation 98, 102 mg, 0.25 mmol) in 1,1,1-trichloroethane (6 mL) at room temperature under nitrogen and the mixture was heated under reflux for 18 hours. The mixture was concentrated under reduced pressure and the residue purified by flash chromatography on silica gel, by gradient elution using hexane:ethyl acetate (7:3 changing to 1:1, by volume) to give the title compound (87 mg, 71%) as a white solid.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 18 hours
  3. concentrationThe mixture was concentrated under reduced pressure
  4. customthe residue purified by flash chromatography on silica gel, by gradient elution

Sources & evidence

ORD record
ord-3324af97aff94e0992cd6e39b6f5bc91
Source dataset
uspto-grants-2002_04
Patent number
US06376490B1

Reaction notes

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