Stannous chloride dihydrate → [4-(4-Fluorophenyl)sulfanylphenyl]hydrazine hydrochloride

Participants

Reaction Conditions

Reaction Steps

A solution of sodium nitrite (5.90 g, 86 mmol) in water (110 mL) is added drop wise to a pre-cooled (−10° C.) slurry of 4-(4-fluorophenyl)sulfanylaniline (14.39 g, 66 mmol) in concentrated hydrochloric acid (250 mL). The resulting mixture is stirred at 0° C. for 15 min and then at room temperature for 30 min. The temperature is lowered to −5° C. and a solution of tin (II) chloride dihydrate (44.4 g, 197 mmol) in concentrated hydrochloric acid (170 mL) is added drop wise. The resulting suspension is stirred at −5° C. for 30 min and is then allowed to warm up to room temperature over 1 h. The off-white solids are isolated by filtration, washed with cold water and then with diethyl ether and finally dried to afford the desired product (18.04 g, 66 mmol, quantitative yield) (HPLC-MS Method 3: retention time: 2.129 min, m/z 235.1).

Provenance & Evidence