3-(Carboxymethyl)rhodanine

PALE YELLOW FINE CRYSTALINE POWDER

General procedure: Mixture of amine or amino acid (1 mol), sodium hydroxide (22 percent) and carbon disulfide (1 mol) in 3 ml water was reacted in a microwave reactor (CEM Discover, Benchmate, USA) for 5 min at 100 °C at 80 W. After automatedcooling to 40 °C, sodium chloroacetate (1 mol) was addedand the mixture was reacted again at 100 °C for 5 min.After cooling (40 °C), conc. HCl (3 ml) was added and thereaction was completed at 110 C for 20–30 min. Thecrude product was extracted with ethyl acetate and purified(Nitsche and Klein, 2012).2-(4-Oxo-2-thioxothiazolidin-3-yl)acetic acid (2a) Yield;82.5 percent; mp 245–247 °C; UV λmax 266, 215 nm; IR(KBr)νmax 3439, 1663, 1512, 1321, 896 cm-1; 1H NMR(DMSO-d6, 400 MHz): δ = 4.56 (2H, s, N–CH2), 4.41(2H, s, H-5); 13C NMR (DMSO-d6, 100 MHz): δ= 202.80(C = S, C-2), 173.72 (C = O, COOH), 167.29 (C = O, C-4), 44.77 (CH2, N–CH2), 35.94 (CH2, C-5); Anal.calcd.for C5H5NO3S2: C, 31.40; H, 2.64; N, 7.32. Found: C, 31.55; H, 2.53; N, 7.22.General Procedure for the Synthesis of Λ/-substituted Rhodanines (7a-f) To a solution of the requisite natural amino acid (typically 5 g, 30 mmol) in water (100 mL) was added NaOH (2.4 g, 2 eq) and CSGeneral procedure: A suspension of amine (5 mmol) and bis(carboxymethyl)trithiocarbonate (5.5 mmol) in water was reacted in a microwave reactor (Monowave 300, Anton Paar) at the different described time and temperature conditions. After automated cooling to 40°C the crude product was extracted with ethyl acetate and purified by flash chromatography (cyclohexane/ethyl acetate) using a Biotage Isolera One system.#10;#10;(b) Preparation of(4~oxo-2-thioxo-l, 3-thiazolidin-3-yl)acetic acid [II]In 250 ml cap. three necked round bottom flask equipped with stirrer, thermometer condenser, and oil bath , Methyl(4-oxo-2-thioxo-l, 3-thiazolidin-3-yl)acetate (28g, 0.1364mol) is stirred Example-5(a) ; Preparation of (4-oxo-2-thioxo~l , 3-thiazolidin-3-yl)acetic acid [II]In 100 ml three necked round bottom flask equipped with stirrer, condenser, thermometer, oil bath, Methyl(4-oxo-2-thioxo-l, 3-thiazolidin-3-yl)acetate (8g, 0.038mol) is stirred with mixture of 25ml acetic acid and 20ml of 25percent sulfuric acid solution at reflux temperature for 2 hours. 20ml 33percent aqueous acetic acid solution is added in the reaction mass. Reflux is maintained for 21 hours. The absence of methyl(4-oxo-2-thioxo-l, 3-thiazolidin~3-yl)acetate is checked by TLC. The reaction mass is dumped into cooled water. Aqueous layer is extracted with ethyl acetate, ethyl acetate layer is distilled out and triturated with 20ml hexane to give (4-oxo-2-thioxo-l, 3-thiazolidin-3-yl)acetic acid [II] as yellow colored product. Yield = 4gm (percentYield= 53.7percent)c) Preparation of

Molecular Weight:191.2
XLogP3:0.4
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:5
Rotatable Bond Count:2
Exact Mass:190.97108537
Monoisotopic Mass:190.97108537
Topological Polar Surface Area:115
Heavy Atom Count:11
Complexity:228
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes