N-bromobutanimide → HCID 58355460, compound

HRID 1184221Notes

Reaction equation

HRID 1184221 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][CH2:5][CH2:6][N:7]1[CH:11]=[CH:10][N:9]=[C:8]1[C:12]([O:14][CH2:15][CH3:16])=[O:13].[Br:17]N1C(=O)CCC1=O>C(#N)C>[Br:17][C:10]1[N:9]=[C:8]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[N:7]([CH2:6][CH2:5][CH2:4][CH2:3][O:2][CH3:1])[CH:11]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 58355716HCID 58355716, compound

Product 1

HCID 58355460HCID 58355460, compoundYield 23.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

Ethyl 1-(4-methoxybutyl)-1H-imidazole-2-carboxylate (2.18 g) was dissolved in acetonitrile (30 ml), N-bromosuccinimide (1.71 g) was added and the mixture was stirred at 60° C. for 14 hr. After cooling to room temperature, the reaction mixture was concentrated under reduced pressure. The residue was subjected to silica gel column chromatography, and a fraction eluted with ethyl acetate-hexane (10:90-70:30) was concentrated under reduced pressure to give the object product (689 mg).

Workup

  1. temperatureAfter cooling to room temperature
  2. concentrationthe reaction mixture was concentrated under reduced pressure
  3. washa fraction eluted with ethyl acetate-hexane (10:90-70:30)
  4. concentrationwas concentrated under reduced pressure

Sources & evidence

ORD record
ord-129a760e65d34a77b538a8f7610d89f8
Source dataset
uspto-grants-2014_03
Patent number
US08664380B2

Reaction notes

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