Reaktion #313331

Reaktionsgleichung

3-(3-chlorosulfonylphenyl)acrylic acid methyl ester

3-(3-Chlorosulfonylphenyl)acrylic acid methyl ester

1-aminonaphthalene

NaHCO3

→

title compound

Ausbeute 51.6%

3-[3-(Naphthalen-1-ylsulfamoyl)-phenyl]-acrylic acid methyl ester

Ausbeute 51.6%

Lösungsmittel

dioxane

dioxane

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe reaction mixture was evaporated
2. 2
   Sonstigethe residue was partitioned between ethyl acetate and 2N HCl
3. 3
   WaschenThe organic layer was washed successively with water, saturated NaCl
4. 4
   Trocknendried (Na2SO4)
5. 5
   SonstigeThe solvent was removed
6. 6
   Sonstigethe residue was chromatographed on silica gel with petroleum ether-ethyl acetate (gradient from 2:1 to 1:1
7. 7
   WaschenThe obtained product was washed with diethyl ether

Vorschrift

A solution of 3-(3-chlorosulfonylphenyl)acrylic acid methyl ester (3) (0.4 g, 1.53 mmol) in dioxane (5 ml) was added to a mixture of 1-aminonaphthalene (0.22 g, 1.53 mmol) in dioxane (1 ml) and NaHCO3 (0.26 g, 3.09 mmol) in water (3 ml), and the resultant solution was stirred at room temperature until the completion of the reaction (control by TLC). The reaction mixture was evaporated and the residue was partitioned between ethyl acetate and 2N HCl. The organic layer was washed successively with water, saturated NaCl, and dried (Na2SO4). The solvent was removed and the residue was chromatographed on silica gel with petroleum ether-ethyl acetate (gradient from 2:1 to 1:1, v/v) as eluent. The obtained product was washed with diethyl ether to give the title compound (0.29 g, 51%) as a white solid. 1H NMR (DMSO-d6, HMDSO), δ: 3.69 (3H, s); 6.56 (1H, d, J=16.0 Hz); 7.16 (1H, dd, J=7.0 and 1.4 Hz); 7.27-8.14 (11H, m); 10.25 (1H, s).

Quelle