2-Nitroimidazole → N-(4-Methylpent-3-en-1-yl)-2-nitroimidazole

HRID 2393787Notes

Reaction equation

HRID 2393787 reaction equation
[N+:1]([C:4]1[NH:5][CH:6]=[CH:7][N:8]=1)([O-:3])=[O:2].C(=O)(O)[O-].[Na+].Br[CH2:15][CH2:16][CH:17]=[C:18]([CH3:20])[CH3:19]>CN(C)C=O.O>[CH3:19][C:18]([CH3:20])=[CH:17][CH2:16][CH2:15][N:5]1[CH:6]=[CH:7][N:8]=[C:4]1[N+:1]([O-:3])=[O:2]

Participants

6

Reactant 3

HCID 107012-NitroimidazoleHCID 1375215-Bromo-2-methyl-2-penteneHCID 516892Sodium Bicarbonate

Product 1

HCID 15186012N-(4-Methylpent-3-en-1-yl)-2-nitroimidazole

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-nitroimidazole (3.0 g, 27 mmol) in dry dimethylformamide (25 mL), was added anhydrous sodium bicarbonate (4.2 g, 50 mmol) followed by 5-bromo-2-methyl-2-pentene (5.0 g, 30.67 mmol). The reaction mixture was heated at 60°-70° C. with stirring under nitrogen for 16 hours. Solvent dimethylformamide and the unreacted bromide were removed under reduced pressure (<1 mm) at 50°-60° C. to yield a paste which was dissolved in water (50 mL) and extracted with ethyl acetate (5×50 mL). The combined organic extracts were dried and concentrated to give a brown oil which was recrystallized from petroleum ether (b.p. 40°-60° C.) to yield a yellow solid. Yield: 4.8 g, m.p. 51°-52° C. 1H NMR (CDCl3) δ 1.55 (s, 3H, CH3), 1.75 (s, 3H, CH3), 2.7 (q, 2H, olefinic CH2), 4.5 (t, 2H, N--CH2), 5.2 (t, 1H, olefinic H), 7.1 (s, 1H, imidazole H), 7.2 (s, 1H, imidazole H). M.S. [M+H]+ 196, [M+NH4 ]+ 213.

Workup

  1. temperatureThe reaction mixture was heated at 60°-70° C.
  2. customSolvent dimethylformamide and the unreacted bromide were removed under reduced pressure (<1 mm) at 50°-60° C.
  3. customto yield a paste which
  4. extractionextracted with ethyl acetate (5×50 mL)
  5. customThe combined organic extracts were dried
  6. concentrationconcentrated
  7. customto give a brown oil which
  8. customwas recrystallized from petroleum ether (b.p. 40°-60° C.)
  9. customto yield a yellow solid

Sources & evidence

ORD record
ord-5a2da90108d74d7eb3aa5cfe3486568f
Source dataset
uspto-grants-1998_09
Patent number
US05808091

Reaction notes

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