Diisopropylethylamine → Ethyl 4-[2-(1-ethylpropyl)-1H-imidazol-1-yl]-3-nitrobenzoate

HRID 72759

Reaction equation

HRID 72759 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].[CH2:16]([CH:18]([C:21]1[NH:22][CH:23]=[CH:24][N:25]=1)[CH2:19][CH3:20])[CH3:17].C(N(CC)C(C)C)(C)C>C(#N)C>[CH2:16]([CH:18]([C:21]1[N:22]([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:23]=[CH:24][N:25]=1)[CH2:19][CH3:20])[CH3:17]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 2411062-pentan-3-yl-1H-imidazoleHCID 21277355Ethyl 4-fluoro-3-nitrobenzoate

Product 1

HCID 59198861Ethyl 4-[2-(1-ethylpropyl)-1H-imidazol-1-yl]-3-nitrobenzoate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Ethyl 4-fluoro-3-nitrobenzoate 9.16 g, 2-(1-ethylpropyl)-1H-imidazole 5.94 g, N,N-diisopropylethylamine 11.2 mL and acetonitrile 86 mL were mixed and heated under reflux for 15 hours in nitrogen atmosphere. From the reaction liquid the solvent was distilled off, and the residue was dissolved in ethyl acetate and rendered weakly alkaline with saturated aqueous sodium hydrogencarbonate solution. The organic layer was separated, washed with water and dried over magnesium sulfate. Distilling the solvent off, 13.16 g of the title compound was obtained.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 15 hours in nitrogen atmosphere
  3. customFrom the reaction liquid the solvent
  4. distillationwas distilled off
  5. dissolutionthe residue was dissolved in ethyl acetate
  6. customThe organic layer was separated
  7. washwashed with water
  8. dry with materialdried over magnesium sulfate
  9. distillationDistilling the solvent off, 13.16 g of the title compound
  10. customwas obtained

Sources & evidence

ORD record
ord-9f5f1f17f6ec42e3a4aec68ef13ac7a5
Source dataset
uspto-grants-2014_09
Patent number
US08829000B2

Linked notes

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