Sodium hydride → Methyl{[(4-ethoxyphenyl)sulfonyl]-4-methylanilino}acetate

HRID 971309Notes

Reaction equation

HRID 971309 reaction equation
[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([S:10]([NH:13][C:14]2[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=2)(=[O:12])=[O:11])=[CH:6][CH:5]=1)[CH3:2].[H-].[Na+].[CH3:23][O:24][C:25](=[O:28])[CH2:26]Br>CN(C=O)C>[CH3:23][O:24][C:25](=[O:28])[CH2:26][N:13]([S:10]([C:7]1[CH:6]=[CH:5][C:4]([O:3][CH2:1][CH3:2])=[CH:9][CH:8]=1)(=[O:11])=[O:12])[C:14]1[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 60984Methyl bromoacetateHCID 9250104-ethoxy-N-(4-methylphenyl)benzenesulfonamide

Product 1

HCID 1108126Methyl{[(4-ethoxyphenyl)sulfonyl]-4-methylanilino}acetateYield 99.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

The crude N-aryl-benzenesulfonamide building block XIII, e.g. 4-ethoxy-N-(4-methylphenyl)benzenesulfonamide (3.087 g, 10.6 mmol), was dissolved in DMF (10 mL) and was added to a suspention of NaH (13.6 mmol, 0.593 mg of NaH 55-65% in oil) in DMF (30 mL). The mixture was stirred 45 min at room temperature. 2-Bromoacetic acid methyl ester (1.45 mL, 15.9 mmol) was added dropwise. The resulting mixture was stirred at room temperature overnight. The solvents were evaporated, affording the desired product, e.g. methyl{[(4-ethoxyphenyl)sulfonyl]-4-methylanilino}acetate (3.816 g, quantitative crude yield) as a light yellow solid, in 96.1% purity by HPLC (MaxPlot detection between 230 and 400 nm).

Workup

  1. stirringThe resulting mixture was stirred at room temperature overnight
  2. customThe solvents were evaporated

Sources & evidence

ORD record
ord-e9ad8abedd4f4aa38d7a37bc1fed00a3
Source dataset
uspto-grants-2007_12
Patent number
US07312358B2

Reaction notes

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