N-bromobutanimide → HCID 18969776, compound

HRID 399069Notes

Reaction equation

HRID 399069 reaction equation
[CH3:1][C:2]1([CH3:27])[C@@H:5]([C:6]2[CH:11]=[CH:10][C:9]([S:12]([CH3:15])(=[O:14])=[O:13])=[CH:8][CH:7]=2)[C@H:4]([C:16]2[CH:21]=[CH:20][C:19]([S:22]([CH3:25])(=[O:24])=[O:23])=[CH:18][CH:17]=2)[C:3]1=[O:26].C1C(=O)N(Br)C(=O)C1>C1C=CC=CC=1>[CH3:1][C:2]1([CH3:27])[C:3](=[O:26])[C:4]([C:16]2[CH:17]=[CH:18][C:19]([S:22]([CH3:25])(=[O:24])=[O:23])=[CH:20][CH:21]=2)=[C:5]1[C:6]1[CH:11]=[CH:10][C:9]([S:12]([CH3:15])(=[O:13])=[O:14])=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 70132882HCID 70132882, compound

Product 1

HCID 18969776HCID 18969776, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a solution of cyclobutenone from step 2 (530 mg) in benzene was added NBS (350 mg). The mixture was heated to reflux for 1.5 hr in the presence of a sun lamp, cooled to r.t. and the solvent evaporated. The resulting residue was purified by flash chromatography (silica gel; hexane/EtOAc (70:30)) to provide the title compound as a white solid, m.p. 212° C.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 1.5 hr in the presence of a sun lamp
  3. customthe solvent evaporated
  4. customThe resulting residue was purified by flash chromatography (silica gel; hexane/EtOAc (70:30))

Sources & evidence

ORD record
ord-62666f595b71405f85e21fe18176655a
Source dataset
uspto-grants-1998_10
Patent number
US05817700

Reaction notes

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