Reaction #2161250

Reaction equation

ethyl 4-nitro-1H-imidazole-2-carboxylate

cyclopropylmethyl bromide

potassium carbonate

→

Ethyl 1-(cyclopropylmethyl)-4-nitro-1H-imidazole-2-carboxylate

Solvents

DMF

water

Conditions

Workup

1. 1
   TemperatureAfter cooling
2. 2
   Extractionextracted four times with ethyl acetate
3. 3
   WashThe combined organic phases are washed once with water and three times with a saturated sodium chloride solution
4. 4
   Dryingdried with magnesium sulfate
5. 5
   Concentrationconcentrated in vacuo
6. 6
   OtherThe crystalline residue is directly used further for the next reaction

Procedure

Under argon, 15 g (81 mmol) of ethyl 4-nitro-1H-imidazole-2-carboxylate are stirred with 13.13 g (97.2 mmol) of cyclopropylmethyl bromide and 22.4 g (162 mmol) of potassium carbonate in 165 ml of DMF at 80° C. for 1 h. After cooling, the reaction mixture is diluted with water and extracted four times with ethyl acetate. The combined organic phases are washed once with water and three times with a saturated sodium chloride solution, dried with magnesium sulfate and concentrated in vacuo. The crystalline residue is directly used further for the next reaction.

Source