N-bromobutanimide → HCID 10471268, compound

HRID 53819Notes

Reaction equation

HRID 53819 reaction equation
[Cl:1][C:2]1[C:3]([N+:14]([O-:16])=[O:15])=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[O:12])[C:6](=[O:13])[NH:5]2.[Br:17]N1C(=O)CCC1=O>CN(C=O)C.O>[Br:17][C:11]1[CH:10]=[C:9]2[C:4]([NH:5][C:6](=[O:13])[C:7](=[O:12])[NH:8]2)=[C:3]([N+:14]([O-:16])=[O:15])[C:2]=1[Cl:1]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 4264803HCID 4264803, compound

Product 1

HCID 10471268HCID 10471268, compoundYield 44%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
28 °C

Procedure

To a stirred solution of 6-chloro-5-nitro-1,4-dihydroquinoxaline-2,3-dione (35 mg, 0.14 mmol) in DMF (0.35 mL), N-bromosuccinimide (39 mg, 0.22 mmol) was added and the solution was stirred at 28° C. for 5 days. The resulting solution was then diluted with water (3.5 mL) and the yellow solid was filtered, washed with water (2.0 mL) and dried to obtain 42 mg crude product as a yellow powder. It was purified by successive crystallization (three times) from DMSO-water (3:1) to furnish 18 mg (44%) of pure title compound as shining yellow flakes, m.p. >350° C.; 1H NMR (DMSO-d6): δ 7.483 (s, 1H), 12.222 (s, 1H), 12.323 (brs, 1H); IR (KBr, cm-1): 3418, 3118, 1700, 1550, 1400, 1350, 1006, 675, 562.

Workup

  1. filtrationthe yellow solid was filtered
  2. washwashed with water (2.0 mL)
  3. customdried
  4. customto obtain 42 mg crude product as a yellow powder
  5. customIt was purified by successive crystallization (three times) from DMSO-water (3:1)

Sources & evidence

ORD record
ord-91289a4aedb942bfbfea77075ae7dc1e
Source dataset
uspto-grants-1997_04
Patent number
US05620979

Reaction notes

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