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

HRID 499903Notes

Reaction equation

HRID 499903 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

15 g (81 mmol) of ethyl 4-nitro-1H-imidazole-2-carboxylate are stirred together 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. under argon 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 saturated sodium chloride solution, dried with magnesium sulphate and evaporated in vacuo. The crystalline residue is further used directly 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 sulphate
  5. customevaporated in vacuo
  6. customThe crystalline residue is further used directly for the next reaction

Sources & evidence

ORD record
ord-0c0bd769542e468bbdf2efb6d8f91247
Source dataset
uspto-grants-2010_08
Patent number
US07767704B2

Reaction notes

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