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

HRID 47170Notes

Reaction equation

HRID 47170 reaction equation
Br[CH2:2][CH2:3][CH:4]=[C:5]([CH3:7])[CH3:6].C([O-])([O-])=O.[K+].[K+].[N+:14]([C:17]1[NH:18][CH:19]=[CH:20][N:21]=1)([O-:16])=[O:15]>CN(C)C=O.C(OCC)C>[CH3:6][C:5]([CH3:7])=[CH:4][CH2:3][CH2:2][N:18]1[CH:19]=[CH:20][N:21]=[C:17]1[N+:14]([O-:16])=[O:15]

Participants

6

Reactant 3

HCID 107012-NitroimidazoleHCID 11430Potassium CarbonateHCID 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 K2CO3 (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) δ1.45 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-301d927b94914e268cbcd3cbef99c291
Source dataset
uspto-grants-2004_03
Patent number
US06699458B2

Reaction notes

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