Dimethylformamide → 2-Nitro-1-(prop-2-ynyl)-1H-imidazole

HRID 1157079Notes

Reaction equation

HRID 1157079 reaction equation
[N+:1]([C:4]1[NH:5][CH:6]=[CH:7][N:8]=1)([O-:3])=[O:2].[CH2:9](Br)[C:10]#[CH:11].C(=O)([O-])[O-].[K+].[K+].CN(C=O)C>CCOC(C)=O>[N+:1]([C:4]1[N:5]([CH2:11][C:10]#[CH:9])[CH:6]=[CH:7][N:8]=1)([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 7842Propargyl bromideHCID 107012-NitroimidazoleHCID 11430Potassium Carbonate

Product 1

HCID 546751432-Nitro-1-(prop-2-ynyl)-1H-imidazoleYield 85.5%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a round bottom flask was added 2-nitroimidazole (500 mg, 4.42 mmol), propargyl bromide (631 mg, 5.31 mmol), potassium carbonate (733 mg, 5.31 mmol) and DMF (5 mL). The reaction was stirred overnight at RT. TLC (EtOAc) indicated complete reaction. The reaction was poured onto water (20 mL) and extracted into EtOAc (3×20 mL). The combined organics were washed with water (5×20 mL). The organic layer was then concentrated in vacuo and purified on a silica gel cartridge using EtOAc:Hex as the eluent to afford 571 mg (85% yield) of 10 as a pale yellow solid. 1H NMR (CDCl3, 400 MHz), δ: 2.63 (1H, d, J=5.6 Hz), 5.23 (2H, d, J=2.4 Hz), 7.20 (1H, d, J=1.2 Hz), 7.46 (1H, s). Mass Spec (lo-res): Calc'd for C6H5N3O2: 151.04; found: 152.10 (M+H).

Workup

  1. customreaction
  2. additionThe reaction was poured onto water (20 mL)
  3. extractionextracted into EtOAc (3×20 mL)
  4. washThe combined organics were washed with water (5×20 mL)
  5. concentrationThe organic layer was then concentrated in vacuo
  6. custompurified on a silica gel cartridge

Sources & evidence

ORD record
ord-a2a76541b7984a3ab2d4e208c38d06c3
Source dataset
uspto-grants-2010_10
Patent number
US07807394B2

Reaction notes

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