N-bromobutanimide → HCID 68297685, compound

HRID 919892Notes

Reaction equation

HRID 919892 reaction equation
C[O:2][C:3](=O)[CH:4]=[CH:5][C:6](=[C:11]([NH:13][CH2:14][C:15]1[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=1)[CH3:12])[C:7]([O:9][CH3:10])=[O:8].C[O-].[Na+].[Br:27]N1C(=O)CCC1=O>CO>[CH3:10][O:9][C:7]([C:6]1[CH:5]=[C:4]([Br:27])[C:3](=[O:2])[N:13]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=2)[C:11]=1[CH3:12])=[O:8]

Participants

5

Reactant 3

HCID 67184N-bromobutanimideHCID 10942334Sodium MethoxideHCID 86714143HCID 86714143, compound

Product 1

HCID 68297685HCID 68297685, compoundYield 60.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

MeOH (120 mL) was added to a flask containing 4-[1-(4-methoxy-benzylamino)-ethylidene]-pent-2-enedioic acid dimethyl ester (5 g, 15.7 mmol). NaOMe solution (3.6 mL, 15.7 mmol, 4.375 M in MeOH) and N-bromosuccinimide (3.35 g, 18.8 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 3.5 g of the title compound. MS: (+) m/z 388.14, 390.15 (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-a16acdc1756d4cfc9c7b1133ce4262a0
Source dataset
uspto-grants-2016_03
Patent number
US09271970B2

Reaction notes

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