Potassium Carbonate → Methyl 3-{[(4-isopropyl-3-methylphenoxy)acetyl]amino}benzoate

HRID 1296814Notes

Reaction equation

HRID 1296814 reaction equation
[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([NH:10][C:11](=[O:14])[CH2:12]Br)[CH:5]=1.[CH:16]([C:19]1[C:24]([CH3:25])=[CH:23][CH:22]=[CH:21][C:20]=1O)([CH3:18])[CH3:17].C(=O)([O-])[O-:28].[K+].[K+]>CC(=O)CC>[CH:16]([C:19]1[CH:20]=[CH:21][C:22]([O:28][CH2:12][C:11]([NH:10][C:6]2[CH:5]=[C:4]([CH:9]=[CH:8][CH:7]=2)[C:3]([O:2][CH3:1])=[O:15])=[O:14])=[CH:23][C:24]=1[CH3:25])([CH3:18])[CH3:17]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 739863-Methyl-2-isopropylphenolHCID 20317589Methyl 3-(2-bromoacetamido)benzoate

Product 1

HCID 730025Methyl 3-{[(4-isopropyl-3-methylphenoxy)acetyl]amino}benzoate

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A solution of 3-(2-bromo-acetylamino)-benzoic acid methyl ester (1.80 g, 6.61 mmol), 4 isopropyl-3-methylphenol (1.00 g, 6.61 mmol) and potassium carbonate (1.00 g, 7.23 mmol) in 2-butanone (15 mL) was heated to reflux under inert atmosphere with stirring for 12 h. After cooling, the mixture was partitioned between water and ethyl acetate (50 mL each). The aqueous phase was extracted with ethyl acetate, and the extracts were washed with brine, combined, dried over magnesium sulfate, filtered and evaporated. The residual material was separated on a column (silica gel) with 20:80 ethyl acetate-hexane, and the eluant containing the product was evaporated to afford pure methyl 3-[2-(4-isopropyl-3-methyl-phenoxy)acetylamino]benzoate, as a glassy solid (1.64 g, 4.80 mmol 73%). TLC RF 0.41 (30:70 ethyl acetate-hexane). 1H NMR (300 MHz, CDCl3): δ 8.39 (1H, br s), 8.05 (1H, t, J=1.8 Hz), 7.99 (1H, ddd, J=8.0, 2.2, 1.1 Hz), 7.80 (1H, dt, J=7.7, 1.3 Hz), 7.42 (1H, t, J=7.9 Hz), 7.18 (1H, d, J=8.8 Hz), 6.81–6.77 (2H, m), 4.57 (2H, s), 3.90 (3H, s), 3.07 (1H, heptet, J=7.0 Hz), 2.32 (3H, s), 1.18 (6H, d, J=7.0 Hz). MS (ESI): m/e 344 (3), 343 (22), 342 (100).

Workup

  1. temperatureto reflux under inert atmosphere
  2. temperatureAfter cooling
  3. customthe mixture was partitioned between water and ethyl acetate (50 mL each)
  4. extractionThe aqueous phase was extracted with ethyl acetate
  5. washthe extracts were washed with brine
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. customevaporated
  9. customThe residual material was separated on a column (silica gel) with 20:80 ethyl acetate-hexane
  10. additionthe eluant containing the product
  11. customwas evaporated

Sources & evidence

ORD record
ord-2a364964a6e8448e983093a840dc5d3f
Source dataset
uspto-grants-2007_07
Patent number
US07247741B2

Reaction notes

Loading…