N-bromobutanimide → HCID 13309908, compound

HRID 325453Notes

Reaction equation

HRID 325453 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:7]=[CH:8][N:9]2[C:18]3[C:13](=[CH:14][C:15]([C:19]([F:22])([F:21])[F:20])=[CH:16][CH:17]=3)[N:12]([CH3:23])[C:11](=[O:24])[C:10]=12)=[O:5])[CH3:2].[Br:25]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[CH2:1]([O:3][C:4]([C:6]1[N:7]=[C:8]([Br:25])[N:9]2[C:18]3[C:13](=[CH:14][C:15]([C:19]([F:22])([F:21])[F:20])=[CH:16][CH:17]=3)[N:12]([CH3:23])[C:11](=[O:24])[C:10]=12)=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 13309890HCID 13309890, compound

Product 1

HCID 13309908HCID 13309908, compoundYield 39.5%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To a solution of 5-methyl-4-oxo-7-trifluoromethyl-4,5-dihydroimidazo[1,5-a]quinoxaline 3-carboxylic acid ethyl ester (3.9 g) in carbon tetrachloride (250 ml) was added N-bromosuccinimide (20 g). The mixture was stirred vigorously and was refluxed for 18 hours. After removal of solvent under water aspirator vacuum the residue was chromatographed via a short silica gel dry column (chloroform as eluant). The product was isolated out as an off-white solid (1.9 g, 39% yield). Recrystallized from acetonitrile, m.p. 205°-207° C.

Workup

  1. temperaturewas refluxed for 18 hours
  2. customAfter removal of solvent under water
  3. customwas chromatographed via a short silica gel
  4. dry with materialdry column (chloroform as eluant)

Sources & evidence

ORD record
ord-8ba3c23fd15e4e52bcc3c8a3b3bc227e
Source dataset
uspto-grants-1984_04
Patent number
US04440929

Reaction notes

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