Methyl iodide → HCID 68454305, compound

HRID 1296817Notes

Reaction equation

HRID 1296817 reaction equation
[H-].[Na+].[CH:3]([C:6]1[CH:25]=[CH:24][C:9]([O:10][CH2:11][C:12]([NH:14][C:15]2[CH:16]=[C:17]([CH:21]=C[CH:23]=2)C([O-])=O)=[O:13])=[CH:8][C:7]=1[CH3:26])([CH3:5])[CH3:4].[CH3:27]I.[C:29]([O:32][CH2:33]C)(=[O:31])[CH3:30]>CN(C=O)C>[CH:3]([C:6]1[CH:25]=[CH:24][C:9]([O:10][CH2:11][C:12]([N:14]([C:15]2[CH:23]=[C:30]([CH:21]=[CH:17][CH:16]=2)[C:29]([O:32][CH3:33])=[O:31])[CH3:27])=[O:13])=[CH:8][C:7]=1[CH3:26])([CH3:4])[CH3:5]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 589137953-[2-(4-Isopropyl-3-methyl-phenoxy)acetylamino]benzoate

Product 1

HCID 68454305HCID 68454305, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A suspension of sodium hydride (0.16 g, 55% w/w) was washed free of mineral oil and taken up in DMF (5 mL). The solution was cooled in an ice bath while a solution of 3-[2-(4-isopropyl-3-methyl-phenoxy)acetylamino]benzoate (0.80 g, 2.34 mmol) in DMF (10 mL) was added. The mixture was allowed to stir for 1 h, then was treated with methyl iodide (0.60 g), and the resulting mixture stirred overnight. It was diluted with ethyl acetate (50 mL), and this was washed with three 50 mL portions of water and then brine. The aqueous phases were back-extracted in sequence with ethyl acetate, and the organic extracts were combined, dried over anhydrous magnesium sulfate, filtered, and evaporated. The residue was separated by column chromatography to afford the product, methyl 3-[N-[2-(4-isopropyl-3-methylphenoxy)-acetyl]-N-methylamino]-benzoate, as a pale yellow oil (0.68 g, 1.91 mmol, 82%). 1H NMR (CDCl3, 300 MHz): δ 8.03 (1H, d, J=7.6 Hz), 7.90 (1H, t, J=2.1 Hz), 7.51 (1H, t, J=7.9 Hz), 7.44 (1H, dd, J=8.0, 1.7 Hz), 7.06 (1H, dd, J=9.1, 5.3 Hz), 6.59–6.52 (1H, m), 4.38 (2H, s), 3.93 (3H, s), 3.32 (3H, s), 3.02 (1H, m, J=7.0 Hz), 2.25 (3H, s), 1.15 (6H, d, J=7.0 Hz). Mass spectrum (ES+): m/z 357 (22), 356 (100).

Workup

  1. washwas washed free of mineral oil
  2. additionwas added
  3. stirringthe resulting mixture stirred overnight
  4. washthis was washed with three 50 mL portions of water
  5. extractionThe aqueous phases were back-extracted in sequence with ethyl acetate
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. customevaporated
  9. customThe residue was separated by column chromatography

Sources & evidence

ORD record
ord-2f1da52a5e934e6a93db0d2f5dd44fa1
Source dataset
uspto-grants-2007_07
Patent number
US07247741B2

Reaction notes

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