N-bromobutanimide → HCID 67267353, compound

HRID 598166Notes

Reaction equation

HRID 598166 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[N:9]1[C:13]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:12][N:11]=[CH:10]1.[Br:19]N1C(=O)CCC1=O>CN(C=O)C.O>[Br:19][C:12]1[N:11]=[CH:10][N:9]([C:3]2[CH:4]=[CH:5][C:6]([CH3:8])=[CH:7][C:2]=2[CH3:1])[C:13]=1[C:14]([O:16][CH2:17][CH3:18])=[O:15]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 67267939HCID 67267939, compound

Product 1

HCID 67267353HCID 67267353, compoundYield 29%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
75 °C

Procedure

To 5.0 g (21 mmol) of ethyl 1-(2,4-dimethylphenyl)-1H-imidazole-5-carboxylate in 40 mL of DMF was added 7.3 g (41 mmol) of N-bromosuccinimide and the resulting solution was heated to 75° C. for 75 min. The reaction was cooled to room temperature, diluted with 400 mL of water and extracted with ethyl acetate. The combined extracts were washed with water and brine, dried over sodium sulfate, filtered and the resulting filtrate was concentrated to an oil. The oil was purified by flash chromatography eluting with a 17-20% ethyl acetate/hexanes gradient mixture to give 1.89 g (29%) of the title compound as a light yellow solid.

Workup

  1. temperatureThe reaction was cooled to room temperature
  2. extractionextracted with ethyl acetate
  3. washThe combined extracts were washed with water and brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationthe resulting filtrate was concentrated to an oil
  7. customThe oil was purified by flash chromatography
  8. washeluting with a 17-20% ethyl acetate/hexanes gradient mixture

Sources & evidence

ORD record
ord-887eef71cd8b4c4f80eaf639f66abd11
Source dataset
uspto-grants-2011_03
Patent number
US07897607B2

Reaction notes

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