Hydrochloric Acid → HCID 86723942, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of (3-benzenesulfonyl-phenyl)-hydrazine (0.824 g, 3.3 mmol), isobutyraldehyde (0.245 g, 3.4 mmol) and toluene (12 mL) was stirred at 20° C. for 2 h. Acetic acid (12 mL) was added, followed by a solution of HCl in 1,4-dioxane (4 M, 0.83 mL, 3.3 mmol) and stirring was continued for 2 h. 1,2-Dichloroethane (12 mL) was added followed by sodium triacetoxyborohydride (1.05 g, 5 mmol) and stirring was continued for 1 h. The mixture was concentrated to 5 mL in vacuo and residue partitioned between saturated aqueous sodium hydrogen carbonate (200 mL) and DCM (3×60 mL). The combined organic extracts were dried (Na2SO4) and evaporated in vacuo to give an orange oil. Chromatography (SiO2; gradient elution with 0-30% Et2O in petrol) gave the title compound (0.044 g). MS: [M+H]+=288.

Provenance & Evidence