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

HRID 1599797Notes

Reaction equation

HRID 1599797 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>[N+:1]([C:4]1[N:5]([CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH:6]=[CH:7][N:8]=1)([O-:3])=[O:2]

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) δ 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-5293f0ce140743cd9faa48fe24f68b24
Source dataset
uspto-grants-1998_04
Patent number
US05741912

Reaction notes

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