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

HRID 2277411Notes

Reaction equation

HRID 2277411 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[NH:7][CH:8]=[C:9]([N+:11]([O-:13])=[O:12])[N:10]=1)=[O:5])[CH3:2].[CH:14]1([CH2:17]Br)[CH2:16][CH2:15]1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.O>[CH2:1]([O:3][C:4]([C:6]1[N:7]([CH2:17][CH:14]2[CH2:16][CH2:15]2)[CH:8]=[C:9]([N+:11]([O-:13])=[O:12])[N:10]=1)=[O:5])[CH3:2]

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

15 g (81 mmol) of 4-nitro-1H-imidazole-2-carboxylic acid ethyl ester is stirred under argon together with 13.13 g (97.2 mmol) of cyclopropyl methyl bromide and 22.4 g (162 mmol) of potassium carbonate in 165 ml of DMF for 1 hour at 80° C. 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 saturated sodium chloride solution, dried with magnesium sulfate, and concentrated by evaporation in a vacuum. The crystalline residue is immediately reused 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 saturated sodium chloride solution
  4. dry with materialdried with magnesium sulfate
  5. concentrationconcentrated by evaporation in a vacuum
  6. customThe crystalline residue is immediately reused for the next reaction

Sources & evidence

ORD record
ord-9578ea938ef54ab9bdc3bbf54999387e
Source dataset
uspto-grants-2015_09
Patent number
US09133165B2

Reaction notes

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