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

HRID 975611Notes

Reaction equation

Br[CH2:2][CH2:3][CH:4]=[C:5]([CH3:7])[CH3:6].[N+:8]([C:11]1[NH:12][CH:13]=[CH:14][N:15]=1)([O-:10])=[O:9].C(=O)([O-])[O-].[K+].[K+]>>[CH3:6][C:5]([CH3:7])=[CH:4][CH2:3][CH2:2][N:12]1[CH:13]=[CH:14][N:15]=[C:11]1[N+:8]([O-:10])=[O:9]

Participants

Reactant 3

HCID 107012-Nitroimidazole

HCID 11430Potassium Carbonate

HCID 1375215-Bromo-2-methyl-2-pentene

Product 1

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

Procedure

5-Bromo-2-methyl-2-pentene (15 g, 0.092 mol) was added to a slurry of 2-nitroimidazole (10.4 g, 0.092 mol) and potassium carbonate (12.7 g, 0.092 mol) and refluxed for 24 hrs. Acetone was removed on a rotary evaporator and the residue was purified by column chromatography. Yield 6.2 g (34%). 1H NMR CDCl3) δ1.44 and 1.68 [s, 6H, =C(CH3)2 ], 2.53 (m, t 2H, CH2CH2CN<), 4.41 (t, 2H, CH2CH2CN<), 5.06 (m, 1H, CH=C), 7.03 and 7.12 (s, 2H, imi H).

Workup

temperaturerefluxed for 24 hrs
customAcetone was removed on a rotary evaporator
customthe residue was purified by column chromatography

Sources & evidence

ORD record: ord-cf9daa59692f4991abcb22dcaa3d834c
Source dataset: uspto-grants-1997_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05608110

Reaction notes

Loading…