N-bromobutanimide → HCID 86714163, compound

HRID 919980Notes

Reaction equation

HRID 919980 reaction equation
C[O:2][C:3](=O)[CH:4]=[CH:5][C:6](=[C:11]([NH:13][C@H:14]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH3:15])[CH3:12])[C:7]([O:9][CH3:10])=[O:8].C[O-].[Na+].[Br:26]N1C(=O)CCC1=O>CO>[CH3:10][O:9][C:7]([C:6]1[CH:5]=[C:4]([Br:26])[C:3](=[O:2])[N:13]([C@H:14]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH3:15])[C:11]=1[CH3:12])=[O:8]

Participants

5

Reactant 3

HCID 67184N-bromobutanimideHCID 10942334Sodium MethoxideHCID 86714162HCID 86714162, compound

Product 1

HCID 86714163HCID 86714163, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

MeOH (150 mL) was added to a flask containing (5)-4-[1-(1-phenyl-ethylamino)-ethylidene]-pent-2-enedioic acid dimethyl ester (4.81 g, 15.9 mmol). NaOMe solution (3.6 mL, 15.9 mmol, 4.375 M in MeOH) and N-bromosuccinimide (3.4 g, 19 mmol) were added, and the resulting mixture was refluxed for 6 h. After cooling to r.t., the solvent was evaporated in vacuo. Saturated NH4Cl (100 mL) was added, and the resulting mixture was extracted with CH2Cl2. The organic layer was dried over MgSO4 and concentrated. The crude product was chromatographed (0-25% EtOAc/hexanes) to give 2.34 g of the title compound as a yellow solid. MS: (+) m/z 372.20, 374.16 (M+Na, 79/81Br).

Workup

  1. temperaturethe resulting mixture was refluxed for 6 h
  2. customthe solvent was evaporated in vacuo
  3. additionSaturated NH4Cl (100 mL) was added
  4. extractionthe resulting mixture was extracted with CH2Cl2
  5. dry with materialThe organic layer was dried over MgSO4
  6. concentrationconcentrated
  7. customThe crude product was chromatographed (0-25% EtOAc/hexanes)

Sources & evidence

ORD record
ord-54a3c0a371ea4d3397fd311371718fd5
Source dataset
uspto-grants-2016_03
Patent number
US09271970B2

Reaction notes

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