Sodium Iodide → Methyl 2-((N-(2-methoxy-2-oxoethyl)-4-methylphenylsulfonamido)methyl)-4-phenoxybenzoate

HRID 1480929Notes

Reaction equation

HRID 1480929 reaction equation
[CH3:1][O:2][C:3](=[O:19])[C:4]1[CH:9]=[CH:8][C:7]([O:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:6][C:5]=1[CH2:17]Cl.[CH3:20][O:21][C:22](=[O:35])[CH2:23][NH:24][S:25]([C:28]1[CH:33]=[CH:32][C:31]([CH3:34])=[CH:30][CH:29]=1)(=[O:27])=[O:26].C([O-])([O-])=O.[K+].[K+].[Na+].[I-]>CN(C=O)C>[CH3:1][O:2][C:3](=[O:19])[C:4]1[CH:9]=[CH:8][C:7]([O:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:6][C:5]=1[CH2:17][N:24]([CH2:23][C:22]([O:21][CH3:20])=[O:35])[S:25]([C:28]1[CH:29]=[CH:30][C:31]([CH3:34])=[CH:32][CH:33]=1)(=[O:27])=[O:26]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 562880Methyl 2-(4-methylphenylsulfonamido)acetateHCID 86709143Methyl 2-(chloromethyl)-4-phenoxybenzoate

Product 1

HCID 89812990Methyl 2-((N-(2-methoxy-2-oxoethyl)-4-methylphenylsulfonamido)methyl)-4-phenoxybenzoateYield 46.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

To a mixture of 2-chloromethyl-4-phenoxy-benzoic acid methyl ester (17.8 g, 64.3 mmol) in DMF (100 mL) was added (toluene-4-sulfonylamino)-acetic acid methyl ester (15.65 g, 64.3 mmol), K2CO3 (17.78 g, 128.6 mmol) and then NaI (964 mg, 6.43 mmol). The resulting mixture was stirred at 50° C. overnight. After cooled, reaction mixture was partitioned between EtOAc and water. The organic layer was washed with water (2×) and brine. It was dried over Na2SO4, filtered and concentrated. Crude residue was purified by silica gel chromatography to provide the title compound (14.34 g, 29.8 mmol). 1H NMR in CDCl3, δ in ppm: 7.86 (d, 1H, 8.8 Hz), 7.70 (d, 2H, J=8.4 Hz), 7.38-6.8 (m, 9H), 4.88 (s, 2H), 3.99 (s, 2H), 3.82 (s, 3H), 3.53 (s, 3H), 2.41 (s, 3H).

Workup

  1. temperatureAfter cooled
  2. customreaction mixture
  3. customwas partitioned between EtOAc and water
  4. washThe organic layer was washed with water (2×) and brine
  5. dry with materialIt was dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customCrude residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-5043ddbe29404d5f93e4066bcde605d1
Source dataset
uspto-grants-2016_08
Patent number
US09409892B2

Reaction notes

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