2-Nitroimidazole → Tert-butyl-(2-nitro-imidazol-1-yl)acetate

HRID 874718Notes

Reaction equation

HRID 874718 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+].[C:15]([O:19][C:20](=[O:23])[CH2:21]Br)([CH3:18])([CH3:17])[CH3:16]>C(#N)C>[C:15]([O:19][C:20](=[O:23])[CH2:21][N:5]1[CH:6]=[CH:7][N:8]=[C:4]1[N+:1]([O-:3])=[O:2])([CH3:18])([CH3:17])[CH3:16]

Participants

5

Reactant 3

HCID 107012-NitroimidazoleHCID 11430Potassium CarbonateHCID 79177tert-Butyl bromoacetate

Product 1

HCID 14555697Tert-butyl-(2-nitro-imidazol-1-yl)acetateYield 71%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

To a mixture of 2-nitroimidazole 1 (17.7 mmol, 1 equiv.) and anhydrous potassium carbonate (70.74 mmol, 4 equiv.) in 20 mL of acetonitrile is added dropwise a solution of tert-butylbromoacetate (17.7 mmol, 1 equiv.) in 10 ml of acetonitrile. The mixture is stirred one night at room temperature and concentrated under vacuum. The residue is purified by chromatography on silica gel using a mixture CH2Cl2/MeOH 95/5 as eluent to give the expected compound as white powder in 71% yield. mp 95-97° C.; 1H NMR (DMSO-d6, 400 MHz) δ 1.46 (s, 9H), 4.99 (s, 2H), 7.06 (d, 1H, J=1.01 Hz), 7.17 (d, 1H, J=1.01 Hz). MS (ESI+/ESI−) m/z 226.15 [M−H]−, 262.13 [M+Cl]−, 250.20 [M+H]+

Workup

  1. concentrationconcentrated under vacuum
  2. customThe residue is purified by chromatography on silica gel using a mixture CH2Cl2/MeOH 95/5 as eluent

Sources & evidence

ORD record
ord-c916c115c86d41d88636d19dae2e8160
Source dataset
uspto-grants-2015_03
Patent number
US08980932B2

Reaction notes

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