2-Bromopropane → HCID 26793695, compound

HRID 1360374Notes

Reaction equation

HRID 1360374 reaction equation
[N+:1]([C:4]1[N:5]=[CH:6][NH:7][CH:8]=1)([O-:3])=[O:2].Br[CH:10]([CH3:12])[CH3:11].C(=O)([O-])[O-].[K+].[K+]>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.C(#N)C>[CH:10]([N:7]1[CH:8]=[C:4]([N+:1]([O-:3])=[O:2])[N:5]=[CH:6]1)([CH3:12])[CH3:11]

Participants

6

Reactant 3

HCID 63582-BromopropaneHCID 11430Potassium CarbonateHCID 178526856HCID 178526856, compound

Product 1

HCID 26793695HCID 26793695, compoundYield 39%

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 6342AcetonitrileSolvent

Procedure

A mixture of 4-nitro-1H-imidazole (1.0 gm, 8.8 mmole), 2-bromopropane (1.1 gm, 8.8 mmole), potassium carbonate (1.8 gm, 13 mmole) and tetrabutylammonium iodide (0.10 gm, 0.27 mmole) in dry acetonitrile (10 mL) was heated at reflux for 7 hr. After cooling to room temperature, the reaction was filtered and the solvents removed from the filtrate. The residue was chromatographed (silica gel column, gradient elution with mixtures of dichloromethane containing 0 to 50% ethyl acetate) to afford the product as a solid (0.52 gm, 39% yield). HPLC retention time=1.12 min; MS (M+H)+=155, 1H NMR (500 MHz, CD3OD) δ 1.56 (d, J=6.71 Hz, 6H) 4.53-4.61 (m, 1H) 7.85 (s, 1H) 8.27 (s, 1H).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 7 hr
  3. filtrationthe reaction was filtered
  4. customthe solvents removed from the filtrate
  5. customThe residue was chromatographed
  6. wash(silica gel column, gradient elution with mixtures of dichloromethane containing 0 to 50% ethyl acetate)

Sources & evidence

ORD record
ord-867bdc42e0964b7b96bc04bf3e8c7bef
Source dataset
uspto-grants-2011_02
Patent number
US07879855B2

Reaction notes

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