تفاعل #1098636

معادلة التفاعل

2-nitroimidazole

propargyl bromide

potassium carbonate

DMF

→

10

المردود 85.5%

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

المردود 85.5%

المذيبات

EtOAc

ظروف التفاعل

المعالجة

1. 1
   أخرىreaction
2. 2
   workup.ADDITIONThe reaction was poured onto water (20 mL)
3. 3
   استخلاصextracted into EtOAc (3×20 mL)
4. 4
   غسيلThe combined organics were washed with water (5×20 mL)
5. 5
   تركيزThe organic layer was then concentrated in vacuo
6. 6
   أخرىpurified on a silica gel cartridge

الإجراء التجريبي

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).

المصدر