Réaction #1244261

Équation de réaction

2-nitroimidazole

propargyl bromide

potassium carbonate

DMF

→

10

Rendement 85.5%

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

Rendement 85.5%

Solvants

EtOAc

Conditions de réaction

Traitement

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

Mode opératoire

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