Reaktion #931374

Reaktionsgleichung

N-(4-chlorophenyl)-2-[((5-bromomethyl-3-chlorothiophen-2-yl)carbonyl)amino]-5-chlorobenzamide

CaCO3

→

N-(4-chlorophenyl)-2-[((5-hydroxymethyl-3-chlorothiophen-2-yl)carbonyl)amino]-5-chlorobenzamide

Ausbeute 56.7%

Lösungsmittel

dioxane

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe resulting turbid solution was heated
2. 2
   Temperaturto reflux for 64 hours
3. 3
   EinengenThe reaction mixture was concentrated
4. 4
   Sonstigeto remove dioxane
5. 5
   Sonstigepurified by flash chromatography on silica
6. 6
   Sonstigefollowed by precipitation from CH2Cl2 and hexane

Vorschrift

To a solution of N-(4-chlorophenyl)-2-[((5-bromomethyl-3-chlorothiophen-2-yl)carbonyl)amino]-5-chlorobenzamide (0.3 g, 0.58 mmol) in dioxane (10 mL) and water (2 mL) was added CaCO3 (0.29 g, 2.89 mmol). The resulting turbid solution was heated to reflux for 64 hours, and then cooled to ambient temperature. The reaction mixture was concentrated to remove dioxane and purified by flash chromatography on silica followed by precipitation from CH2Cl2 and hexane to afford 0.15 g of N-(4-chlorophenyl)-2-[((5-hydroxymethyl-3-chlorothiophen-2-yl)carbonyl)amino]-5-chlorobenzamide, as a yellow solid; NMR (DMSO-d6/TFA) 11.1 (s, 1), 10.7 (s, 1), 8.4 (d, 1), 7.9 (s, 1), 7.7 (d, 2), 7.5 (d, 1), 7.3 (d, 2), 7.0 (s, 1), 4.6(s, 2) ppm.

Quelle