HCID 67241358, compound → HCID 67241888, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-(2-chloroethylthio)-N-isobutyl-3-nitrobenzamide (2.38 g, 8.32 mmol) in AcOH (100 mL) was added iron (1.859 g, 33.3 mmol). The mixture was heated to 70° C. and the reaction was allowed to stir for 1 hour. The reaction turned from a dark solution to a light grey slurry. LCMS analysis of the reaction mixture indicated consumption of starting material. The reaction mixture was concentrated in vacuo and the resulting solid was diluted with H2O (250 mL). The pH of the solution was adjusted to 6 by addition of solid K3PO4. The resulting slurry was extracted with EtOAc (4×100 mL). The combined organics were washed with saturated aqueous NaHCO3 (50 mL) and brine (50 mL). The combined organics were then dried over Na2SO4 and concentrated in vacuo. The product, 3-amino-4-(2-chloroethylthio)-N-isobutylbenzamide, was used without further purification. Product yield was assumed to be 100% (2.38 g, 8.32 mmol) for future calculations. LCMS (+ESI) m/z=287.11 [M+H]+.

Provenance & Evidence