Ethyl bromoacetate → ethyl 2-(2-nitro-1H-imidazol-1-yl)acetate

HRID 1779742Notes

Reaction equation

HRID 1779742 reaction equation
[N+:1]([C:4]1[NH:5][CH:6]=[CH:7][N:8]=1)([O-:3])=[O:2].C([O-])([O-])=O.[K+].[K+].Br[CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18].CCCCCC.C(OCC)(=O)C>CC(C)=O>[CH2:20]([O:19][C:17](=[O:18])[CH2:16][N:5]1[CH:6]=[CH:7][N:8]=[C:4]1[N+:1]([O-:3])=[O:2])[CH3:21]

Participants

6

Reactant 4

HCID 7748Ethyl bromoacetateHCID 107012-NitroimidazoleHCID 11430Potassium CarbonateHCID 21226206Ethyl acetate hexane

Product 1

HCID 327541ethyl 2-(2-nitro-1H-imidazol-1-yl)acetate

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a mixture of 2-nitroimidazole (8 g, 70 mmol) and dry K2CO3 (9.7 g, 70 mmol) in acetone (100 mL) was added ethyl bromoacetate (11.6 g, 70 mmol). The suspension was stirred under N2 atmosphere for 48 h. TLC (silica gel, 40% hexane-ethyl acetate) showed a single UV-visible spot with Rf =0.55. The suspension was filtered and solid was washed with acetone (3×50 mL). The filtrate and the washings were combined and evaporated on a rotary evaporator to afford a thick yellow oil. Yield: 13.9 (99%). MS: 217 (M+NH4)+, 200 (M+H)+. 1H NMR (CDCl3) ε 1.30 (t, 3H, OCH2CH3), 4.26 (q, 2H, OCH2CH3), 5.12 (s, 2H, CH2CO), 7.09 and 7.21 (s, 2H, imidazolyl-H).

Workup

  1. filtrationThe suspension was filtered
  2. washsolid was washed with acetone (3×50 mL)
  3. customevaporated on a rotary evaporator
  4. customto afford a thick yellow oil

Sources & evidence

ORD record
ord-11604981d96544bdba859a2c518b5082
Source dataset
uspto-grants-1997_05
Patent number
US05627286

Reaction notes

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