Diisopropylethylamine → Ethyl 4-(2-isopropyl-1H-imidazol-1-yl)-3-nitrobenzoate

HRID 72757

Reaction equation

HRID 72757 reaction equation
F[C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][C:3]=1[N+:13]([O-:15])=[O:14].[CH:16]([C:19]1[NH:20][CH:21]=[CH:22][N:23]=1)([CH3:18])[CH3:17].C(N(CC)C(C)C)(C)C>C(#N)C>[CH:16]([C:19]1[N:20]([C:2]2[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][C:3]=2[N+:13]([O-:15])=[O:14])[CH:21]=[CH:22][N:23]=1)([CH3:18])[CH3:17]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 1234571H-Imidazole, 2-(1-methylethyl)-HCID 21277355Ethyl 4-fluoro-3-nitrobenzoate

Product 1

HCID 59198553Ethyl 4-(2-isopropyl-1H-imidazol-1-yl)-3-nitrobenzoateYield 81.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of ethyl 4-fluoro-3-nitrobenzoate 4.26 g, 2-isopropylimidazole 2.20 g, N,N-diisopropylethylamine 5.2 mL and acetonitrile 40 mL was heated under reflux for 24 hours. After distilling the solvent off, water was added to the residue and extracted with ethyl acetate. The organic layer was washed with brine, dried over magnesium sulfate and removed of the solvent by distillation, to provide 4.95 g of the title compound.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 24 hours
  3. distillationAfter distilling the solvent off, water
  4. additionwas added to the residue
  5. extractionextracted with ethyl acetate
  6. washThe organic layer was washed with brine
  7. dry with materialdried over magnesium sulfate
  8. customremoved of the solvent by distillation

Sources & evidence

ORD record
ord-5ec2d21edca24238b918011c1f187676
Source dataset
uspto-grants-2014_09
Patent number
US08829000B2

Linked notes

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