Triethylamine → 2-(3-Pyridinyl)-1,3-thiazol-5-amine

Beteiligte Stoffe

Reaktionsbedingungen

Reaktionsschritte

To a dry 500 ml round bottom flask equipped with magnetic stirrer, thermometer, bleach scrubber, and addition funnel was charged 27.6 g (179 mmoles) of aminoacetonitrile bisulfate, and 200 mLs of anhydrous methanol. The solution was cooled to ˜0° C. and 24.15 g (239 mmoles) of triethyl amine was added dropwise at a rate that maintained the temperature below 10° C. After 10 minutes, 20.2 g (119 mmoles) of methyl pyridine-3-carbodithioate was added dropwise in 50 mLs of anhydrous methanol. The reaction mixture was stirred at ambient temperature for 20 hours, after which, the solvent was removed under vacuum on a rotary evaporator. The residue was poured into 500 mLs of water and extracted with methylene chloride (4×100 mLs). The combined methylene chloride extracts were washed with 100 mLs of water, 100 mLs of saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, filtered, and concentrated under vacuum on a rotary evaporator. The crude product was suspended in 100 mLs of ethyl ether, and the resulting yellow solid was collected by vacuum filtration to afford 14.1 g (66%) of a pale yellow solid: 1H NMR (400 MHz, DMSO-d6) δ 8.97 (d, J=2.2 Hz, 1H), 8.53 (dd, J=4.8, 1.6 Hz, 1H), 8.12-8.03 (m, 1H), 7.45 (dd, J=7.9, 4.8 Hz, 1H), 6.99 (s, 1H), 6.28 (bs, 2H); 13C-NMR (101 MHz, CDCl3) δ 151.72, 148.55, 146.06, 145.40, 131.57, 130.18, 129.93, 122.20.

Herkunft & Nachweise