N-bromobutanimide → HCID 68297544, compound

HRID 919861Notes

Reaction equation

HRID 919861 reaction equation
C[O:2][C:3](=O)[CH:4]=[CH:5][C:6](=[C:11]([NH:13][CH2:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[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]([CH2:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:11]=1[CH3:12])=[O:8]

Participants

5

Reactant 3

HCID 67184N-bromobutanimideHCID 10942334Sodium MethoxideHCID 86714136HCID 86714136, compound

Product 1

HCID 68297544HCID 68297544, compoundYield 71.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

MeOH (220 mL) was added to a flask containing 4-(1-phenethylamino-ethylidene)-pent-2-enedioic acid dimethyl ester (7.0 g, 23.1 mmol). NaOMe solution (5.3 mL, 23.1 mmol, 4.375 M in MeOH) and N-bromosuccinimide (4.93 g, 27.7 mmol) were added, and the resulting mixture was refluxed for 1 h. After cooling to r.t., the solvent was evaporated in vacuo. The residue was partitioned between saturated NH4Cl (200 mL) and CH2Cl2 (200 mL). The aqueous layer was extracted with additional CH2Cl2 and the organic layers were combined, dried over MgSO4, and concentrated. The crude product was chromatographed (0-40% EtOAc/hexanes) to give 5.75 g of the title compound as a pale yellow solid. MS: (+) m/z 372.14, 374.16 (M+Na, 79/81Br).

Workup

  1. temperaturethe resulting mixture was refluxed for 1 h
  2. customthe solvent was evaporated in vacuo
  3. customThe residue was partitioned between saturated NH4Cl (200 mL) and CH2Cl2 (200 mL)
  4. extractionThe aqueous layer was extracted with additional CH2Cl2
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated
  7. customThe crude product was chromatographed (0-40% EtOAc/hexanes)

Sources & evidence

ORD record
ord-7dd2223ef0584ea1a0081eda9f8dd83f
Source dataset
uspto-grants-2016_03
Patent number
US09271970B2

Reaction notes

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