Chloroacetic Acid → 3-(4-Oxo-2-thioxo-thiazolidin-3-yl)-cyclohexanecarboxylic acid

Participants

Reaction Steps

To a round bottom flask containing 3-amino-cyclohexanecarboxylic acid (3.80 g, 26.54 mmol) was added aqueous potassium hydroxide (3 g, 53.08 mmol) in water (20 mL). The reaction mixture was stirred at room temperature for 15 minutes. Carbon disulfide (1.60 mL, 26.54 mmol) was added drop-wise to the reaction mixture and stirred at room temperature for 1.5 h. The reaction mixture was then cooled to 0° C. and an aqueous solution of chloroacetic acid (2.5 g, 26.54 mmol) and potassium hydroxide (1.5 g, 26.54 mmol) in water (15 mL) was added slowly to the reaction mixture. The cooling bath was removed and the reaction mixture stirred at room temperature for 1.5 h. The reaction mixture was cooled to 0° C. and acidified with concentrated sulfuric acid (3 mL). The cooling bath was removed and the reaction mixture was heated at 100° C. for 8 h and then allowed to cool to room temperature overnight. The solid was filtered, washed with water (15 mL), 1:1 hexanes/ether (100 mL) and hexanes (100 mL). The solid was dried in a vacuum oven at 55-60° C. for 5 h to afford 3-(4-oxo-2-thioxo-thiazolidin-3-yl)-cyclohexanecarboxylic acid (1.46 g, 21%) as a solid. 1H NMR (400 MHz, DMSO-d6): δ 1.16-1.39 (2H, m), 1.57 (1H, m), 1.79-1.89 (3H, m), 1.96-2.36 (3H, m), 4.12 (2H, s), 4.79 (1H, m), 12.18 (1H, s); APCI-MS: 258.31

Provenance & Evidence