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

HRID 634890Notes

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]>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

Conditions

Temperature: 65 °C

Procedure

To a solution of 2-nitroimidazole (3.0 g, 27 mmol) in dry dimethylformaide (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

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

Sources & evidence

ORD record: ord-79cd2a7861c241008419909728c9f4fc
Source dataset: uspto-grants-2001_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06184361B2

Reaction notes

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