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). To this reaction mixture was added acetic acid (5.0-fold, V/W of starting material), followed by 5-tert-butylsulfanyl-2,2-dimethyl-4-oxo-pentanoic acid ethyl ester (1.05 eq) and NaOAc (2.3 eq). The reaction mixture was agitated at room temperature for about 4 days after which cold water (15.0-fold, V/W of starting material) was added to the reaction and stirred for about 30 minutes. The organic layer was collected and the aqueous layer washed with toluene to recover additional product. The organic portions were collected and washed with water and saturated brine solution. The organic layer was subsequently dried over Na2SO4 and concentrated under reduced pressure. A slurry of collected compound was made with methanol (5.0-fold, V/W of starting material) at 0-5° C. for about 4 hours. The solid was collected and washed with cold methanol. Any remaining solvent was removed by drying under reduced pressure.

Provenance & Evidence