N-bromobutanimide → HCID 68297702, compound

HRID 919941Notes

Reaction equation

HRID 919941 reaction equation
C[O:2][C:3](=O)[CH:4]=[CH:5][C:6](=[C:11]([NH:13][CH2:14][C:15]1[S:16][CH:17]=[CH:18][N:19]=1)[CH3:12])[C:7]([O:9][CH3:10])=[O:8].C[O-].[Na+].[Br:24]N1C(=O)CCC1=O>CO>[CH3:10][O:9][C:7]([C:6]1[CH:5]=[C:4]([Br:24])[C:3](=[O:2])[N:13]([CH2:14][C:15]2[S:16][CH:17]=[CH:18][N:19]=2)[C:11]=1[CH3:12])=[O:8]

Participants

5

Reactant 3

HCID 67184N-bromobutanimideHCID 10942334Sodium MethoxideHCID 86714155HCID 86714155, compound

Product 1

HCID 68297702HCID 68297702, compoundYield 22.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

MeOH (60 mL) was added to a flask containing 4-{1-[(thiazol-2-ylmethyl)-amino]-ethylidene}-pent-2-enedioic acid dimethyl ester (2.12 g, 7.16 mmol). NaOMe solution (1.64 mL, 7.16 mmol, 4.375 M in MeOH) and N-bromosuccinimide (1.53 g, 8.59 mmol) were added, and the resulting mixture was refluxed for 1 h. After cooling to r.t., the solvent was evaporated in vacuo. Saturated NH4Cl was added, and the resulting mixture was extracted with CH2Cl2. The organic layer was dried over MgSO4 and concentrated. The crude product was chromatographed (0-80% EtOAc/hexanes) to give 551 mg of the title compound as a yellow solid. MS: (+) m/z 343.11, 345.12 (M+1, 79/81Br).

Workup

  1. temperaturethe resulting mixture was refluxed for 1 h
  2. customthe solvent was evaporated in vacuo
  3. additionSaturated NH4Cl 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 (0-80% EtOAc/hexanes)

Sources & evidence

ORD record
ord-e10295dbe8544f09a795a2a8d72ca35a
Source dataset
uspto-grants-2016_03
Patent number
US09271970B2

Reaction notes

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