Triethylamine → 2-Isopropyl-4-nitro-benzoic acid 2-(2-isopropyl-imidazol-1-yl)-ethyl ester

HRID 1910796Notes

Reaction equation

HRID 1910796 reaction equation
Br[CH2:2][CH2:3][O:4][C:5](=[O:18])[C:6]1[CH:11]=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[CH:8][C:7]=1[CH:15]([CH3:17])[CH3:16].C(N(CC)CC)C.[CH:26]([C:29]1[NH:30][CH:31]=[CH:32][N:33]=1)([CH3:28])[CH3:27]>CN(C=O)C.O>[CH:26]([C:29]1[N:30]([CH2:2][CH2:3][O:4][C:5](=[O:18])[C:6]2[CH:11]=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[CH:8][C:7]=2[CH:15]([CH3:17])[CH3:16])[CH:31]=[CH:32][N:33]=1)([CH3:28])[CH3:27]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 1234571H-Imidazole, 2-(1-methylethyl)-HCID 671063212-Isopropyl-4-nitro-benzoic acid 2-bromo-ethyl ester

Product 1

HCID 671069432-Isopropyl-4-nitro-benzoic acid 2-(2-isopropyl-imidazol-1-yl)-ethyl esterYield 43.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

2-Isopropyl-4-nitro-benzoic acid 2-bromo-ethyl ester (0.19 g, 0.6 mmol) was dissolved in DMF (5 mL), then triethylamine (0.5 mL, 3.6 mmol) and 2-isopropylimidazole (0.2 g, 1.8 mmol) were added. The mixture was heated at reflux for 15 h then allowed to cool, diluted with water and extracted with ethyl acetate. The organic phase was washed with water and brine, dried over sodium sulfate and concentrated. The crude product was purified by column chromatography on silica gel (60-120 mesh), eluting with ethyl acetate, to afford 2-isopropyl-4-nitro-benzoic acid 2-(2-isopropyl-imidazol-1-yl)-ethyl ester (90 mg, 43%) as an oil.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 15 h
  3. temperatureto cool
  4. extractionextracted with ethyl acetate
  5. washThe organic phase was washed with water and brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated
  8. customThe crude product was purified by column chromatography on silica gel (60-120 mesh)
  9. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-910ae62a44824098a08c9d1881ef5e13
Source dataset
uspto-grants-2013_12
Patent number
US08604029B2

Reaction notes

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