Toluene → HCID 44474264, compound

Participants

Reaction Steps

N-(4-Bromo-benzyl)-N-(4-methoxy-phenyl)-hydrazine hydrochloride (1.0 eq) was added to a reaction flask containing toluene (10.0-fold, V/W of starting material) under nitrogen. Acetic acid (5.0-fold, V/W of starting material) was added, followed by 5-tert-butylsulfanyl-2,2-dimethyl-4-oxo-pentanoic acid ethyl ester (1.05 eq) and sodium acetate (2.3 eq), and the reaction mixture was stirred at room temperature for 4 days. Cold water (15.0-fold, V/W of starting material) was then added to the reaction, and the mixture was agitated for 30 minutes. The organic layer was separated, and the aqueous layer was extracted with toluene (2.0-fold, V/W of starting material) to recover additional product. The combined organic layers were washed with water and brine, dried over sodium sulfate, and concentrated under reduced pressure. A slurry of the crude material was made in methanol (5.0-fold, V/W of starting material), and the mixture was cooled to 0-5° C. for 4 hours. The solid was collected by filtration and washed with cold methanol, and the isolated material was dried under reduced pressure at 28-30° C.

Provenance & Evidence