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

HRID 2074068Notes

Reaction equation

HRID 2074068 reaction equation
[N+:1]([C:4]1[N:5]=[C:6]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[NH:7][CH:8]=1)([O-:3])=[O:2].[CH:14]1([CH2:17]Br)[CH2:16][CH2:15]1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.O>[CH:14]1([CH2:17][N:7]2[CH:8]=[C:4]([N+:1]([O-:3])=[O:2])[N:5]=[C:6]2[C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH2:16][CH2:15]1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 81503BromomethylcyclopropaneHCID 178470305HCID 178470305, compound

Product 1

HCID 59421751Ethyl 1-(cyclopropylmethyl)-4-nitro-1H-imidazole-2-carboxylate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

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.

Workup

  1. temperatureAfter cooling
  2. extractionextracted four times with ethyl acetate
  3. washThe combined organic phases are washed once with water and three times with a saturated sodium chloride solution
  4. dry with materialdried with magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe crystalline residue is directly used further for the next reaction

Sources & evidence

ORD record
ord-23bc4e7f17454e83900db210da16f2fe
Source dataset
uspto-grants-2011_04
Patent number
US07919489B2

Reaction notes

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