N-bromobutanimide → HCID 68929209, compound

HRID 919878Notes

Reaction equation

HRID 919878 reaction equation
C[O:2][C:3](=O)[CH:4]=[CH:5][C:6](=[C:11]([NH:13][CH3:14])[CH3:12])[C:7]([O:9][CH3:10])=[O:8].C[O-].[Na+].[Br:19]N1C(=O)CCC1=O>CO>[CH3:10][O:9][C:7]([C:6]1[CH:5]=[C:4]([Br:19])[C:3](=[O:2])[N:13]([CH3:14])[C:11]=1[CH3:12])=[O:8]

Participants

5

Reactant 3

HCID 67184N-bromobutanimideHCID 10942334Sodium MethoxideHCID 86714140HCID 86714140, compound

Product 1

HCID 68929209HCID 68929209, compoundYield 45.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

MeOH (45 mL) was added to a flask containing 4-(1-methylamino-ethylidene)-pent-2-enedioic acid dimethyl ester (0.97 g, 4.55 mmol). NaOMe solution (1.04 mL, 4.55 mmol, 4.375 M in MeOH) and N-bromosuccinimide (0.97 g, 5.46 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 and CH2Cl2. The aqueous layer was extracted with additional CH2Cl2 and the organic layers were combined, dried over MgSO4, and concentrated. The crude product was chromatographed (0-50% EtOAc/hexanes) to give 540 mg of the title compound. MS: (+) m/z 260.22, 262.18 (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 and CH2Cl2
  4. extractionThe aqueous layer was extracted with additional CH2Cl2
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated
  7. customThe crude product was chromatographed (0-50% EtOAc/hexanes)

Sources & evidence

ORD record
ord-de85d7405d584498879b2f0df2ef7cb6
Source dataset
uspto-grants-2016_03
Patent number
US09271970B2

Reaction notes

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