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

HRID 2393798Notes

Reaction equation

HRID 2393798 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]>CN(C)C=O.C(OCC)C>[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

5

Reactant 2

HCID 107012-NitroimidazoleHCID 1375215-Bromo-2-methyl-2-pentene

Product 1

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

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
75 °C

Procedure

5-Bromo-2-methyl-2-pentene (25 g, 0.154 mol) was dissolved in dry dimethylformamide (DMF) (200 mL). To the solution was added K2 CO3 (21.3 g, 0.154 mol) and 2-nitroimidazole (17.4 g, 0.154 mol). The mixture was stirred under N2 atmosphere at 75° C. for 48 hours. DMF was evaporated on a rotary evaporator. The yellow gummy residue was stirred with water (150 mL) to give yellow solid, which was dissolved in diethyl ether (150 mL), dried over Na2SO4 and evaporated on a rotary evaporator to yield the title product. Yield 27.8 g (92%). mp: 49°-51° C. MS: (M+H)+ =196, M+ =195. 1H NMR (CDCl3) δ 1.45 and 1.68 (s, 6H, gem-di-CH3), 2.52 (q, 2H, CH2CH=), 4.43 [t, 2H, CH2 -(2-nitroimidazolyl)], 5.08 (t, 1H, CH2CH=), 7.05 and 7.14 (s, 2H, 2-nitroimidazolyl-H).

Workup

  1. customDMF was evaporated on a rotary evaporator
  2. stirringThe yellow gummy residue was stirred with water (150 mL)
  3. customto give yellow solid, which
  4. dry with materialdried over Na2SO4
  5. customevaporated on a rotary evaporator

Sources & evidence

ORD record
ord-4f0b788bebc24e9792f503c016286f05
Source dataset
uspto-grants-1998_09
Patent number
US05808091

Reaction notes

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