Ethylamine → (3-Ethylsulfamoyl-phenyl)-acetic acid methyl ester

HRID 2108726Notes

Reaction equation

HRID 2108726 reaction equation
Cl[S:2]([C:5]1[CH:6]=[C:7]([CH2:11][C:12]([O:14][CH3:15])=[O:13])[CH:8]=[CH:9][CH:10]=1)(=[O:4])=[O:3].[CH2:16]([NH2:18])[CH3:17]>C1COCC1.C(OCC)(=O)C>[CH3:15][O:14][C:12](=[O:13])[CH2:11][C:7]1[CH:8]=[CH:9][CH:10]=[C:5]([S:2](=[O:4])(=[O:3])[NH:18][CH2:16][CH3:17])[CH:6]=1

Participants

5

Reactant 2

HCID 6341EthylamineHCID 23388821Methyl [3-(chlorosulfonyl)phenyl]acetate

Product 1

HCID 57421970(3-Ethylsulfamoyl-phenyl)-acetic acid methyl esterYield 93%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

Methyl 2-(3-chlorosulfonyl-phenyl)acetate (0.29 g, 1.17 mmol) was dissolved in THF (10 mL) and to this solution 1 mL (2 mmol) of 2M ethylamine in THF was added. Let stir at room temperature 30 minutes, diluted with ethyl acetate and the organic layer was washed with 10% citric acid, brine, dried over sodium sulfate and concentrated to an oil. 0.28 g, 1.09 mmol, 93% yield. 1H NMR 500 MHz (CDCl3) 7.72 ppm, 2H, m; 7.41 ppm, 2H, m; 4.32 ppm, 1H, t; 3.68 ppm, 3H, s; 3.67 ppm, 2H, s; 2.98 ppm, 2H, m; 1.07 ppm, 3H, t.

Workup

  1. additionwas added
  2. washthe organic layer was washed with 10% citric acid, brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated to an oil

Sources & evidence

ORD record
ord-6e1d77dbe7a34683964b2ad6e98a2ab9
Source dataset
uspto-grants-2009_04
Patent number
US07514448B2

Reaction notes

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