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N-bromobutanimide → 1-(-4-bromo-1-methyl-1H-imidazol-2-yl)-2,2,2-trichloroethanone

HRID 1025551
Notes
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Reaction equation

HRID 1025551 reaction equation
[Cl:1][C:2]([Cl:12])([Cl:11])[C:3]([C:5]1[N:6]([CH3:10])[CH:7]=[CH:8][N:9]=1)=[O:4].C1C(=O)N([Br:20])C(=O)C1>C1COCC1>[Br:20][C:8]1[N:9]=[C:5]([C:3](=[O:4])[C:2]([Cl:1])([Cl:11])[Cl:12])[N:6]([CH3:10])[CH:7]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 112991222,2,2-Trichloro-1-(1-methylimidazol-2-yl)ethanone

Product 1

HCID 709222631-(-4-bromo-1-methyl-1H-imidazol-2-yl)-2,2,2-trichloroethanoneYield 58.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-10 °C

Procedure

To the solution of 2,2,2-trichloro-1-(1-methyl-1H-imidazol-2-yl)ethanone (1.5 g, 6.6 mmol) in 26 mL of anhydrous THF was added 2.35 g of NBS at −10° C. The resulting mixture was stirred at −10° C. for 2 h, then 25° C. for 16 h. The solution was evaporated and the residue was purified by silica gel column (DCM as eluent) to give 1-(-4-bromo-1-methyl-1H-imidazol-2-yl)-2,2,2-trichloroethanone (1.18 g, yield 58%). 1H NMR (300 MHz, CDCl3) δ 7.15 (s, 1H), 4.05 (s, 3H).

Workup

  1. wait25° C. for 16 h
  2. customThe solution was evaporated
  3. customthe residue was purified by silica gel column (DCM as eluent)

Sources & evidence

ORD record
ord-16ce7b993ae54b7eb52f787a05496fd1
Source dataset
uspto-grants-2014_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08729078B2

Reaction notes

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