Chlorosuccinimide → 4-Chloro-2-(pyridin-3-yl)-1,3-thiazol-5-amine hydrochloride

Participants

Reaction Conditions

Reaction Steps

To a dry 250 ml round bottom flask equipped with magnetic stirrer, was charged 6.3 g (35.5 mmoles) of 2-(pyridin-3-yl)-1,3-thiazol-5-amine, and 100 mLs of anhydrous 1,4-dioxane. The solution was cooled to ˜0° C. and 4.75 g (35.5 mmoles) of N-chlorosuccinimide was added portionwise at a rate that maintained the temperature below 10° C. The reaction mixture was stirred at 5-10° C. for 20 minutes, and then filtered through a small pad of diatomaceous earth. The filtrate was diluted with 50 mLs of diethyl ether, and acidified with 10 mLs of 4.0 M HCl in 1,4-dioxane. The resulting solid was collected by vacuum filtration, washed with ethyl ether (100 mLs) and methylene chloride (500 mLs), and then dried in vacuuo at 40° C. to afford 7.5 g (85%) of an orange solid: 1H NMR (400 MHz, DMSO-d6) δ 9.08 (d, J=2.1 Hz, 1H), 8.76 (dt, J=9.5, 4.7 Hz, 1H), 8.66 (ddd, J=8.3, 2.0, 1.3 Hz, 1H), 7.97 (dt, J=15.6, 7.8 Hz, 1H).

Provenance & Evidence