Reaction #1244261

Reaction equation

2-nitroimidazole

propargyl bromide

potassium carbonate

DMF

→

10

Yield 85.5%

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

Yield 85.5%

Solvents

EtOAc

Conditions

Workup

1. 1
   Otherreaction
2. 2
   workup.ADDITIONThe reaction was poured onto water (20 mL)
3. 3
   Extractionextracted into EtOAc (3×20 mL)
4. 4
   WashThe combined organics were washed with water (5×20 mL)
5. 5
   ConcentrationThe organic layer was then concentrated in vacuo
6. 6
   Otherpurified on a silica gel cartridge

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).

Source