N-bromobutanimide → HCID 178470341, compound

HRID 1887243Notes

Reaction equation

HRID 1887243 reaction equation
[CH3:1][C:2]1[N:3]=[CH:4][NH:5][C:6]=1[C:7]([O:9][CH2:10][CH3:11])=[O:8].[Br:12]N1C(=O)CCC1=O>C(#N)C.C(Cl)(Cl)Cl>[Br:12][C:4]1[NH:5][C:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[C:2]([CH3:1])[N:3]=1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 178470400HCID 178470400, compound

Product 1

HCID 178470341HCID 178470341, compoundYield 62.1%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6342AcetonitrileSolvent

Procedure

To a stirred suspension of ethyl 4-methyl-1H-imidazole-5-carboxylate (2.00 g, 13.0 mmol) in acetonitrile (25 mL) and chloroform (25 mL) was added N-bromosuccinimide (2.31 g, 13.0 mmol). The reaction mixture was stirred under nitrogen atmosphere for 20 h, then concentrated in vacuo. The residue was dissolved in ethyl acetate (100 mL) and washed with saturated aqueous sodium bicarbonate (50 mL). The organic layer was dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography eluting with 50% ethyl acetate in hexanes to afford ethyl 2-bromo-4-methyl-1H-imidazole-5-carboxylate as a light yellow solid (1.88 g, 62%): 1H NMR (300 MHz, CDCl3) δ 4.35 (q, J=7.1 Hz, 2H), 2.51 (s, 3H), 1.37 (t, J=7.1 Hz, 3H); MS (ES+) m/z 233.1 (M+1), 235.1 (M+1).

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutionThe residue was dissolved in ethyl acetate (100 mL)
  3. washwashed with saturated aqueous sodium bicarbonate (50 mL)
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by column chromatography
  8. washeluting with 50% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-63e24db2b9fc49389353ad0c3defff62
Source dataset
uspto-grants-2013_08
Patent number
US08501746B2

Reaction notes

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