[S:1]1[CH2:5][CH2:4][NH:3][C:2]1=[O:6].C(=O)([O-])[O-].[K+].[K+].Cl.[CH3:14][N:15]([CH3:20])[CH2:16][CH2:17][CH2:18]Cl.C1OCCOCCOCCOCCOCCOC1>C(#N)C>[CH3:14][N:15]([CH3:20])[CH2:16][CH2:17][CH2:18][N:3]1[CH2:4][CH2:5][S:1][C:2]1=[O:6]
To a solution of 2-thiazolidinone (4.15 g, 40.18 mmol) in acetonitrile (60 ml) were added potassium carbonate (13.3 g 96.2 mmol), N,N-dimethyl-3-aminopropyl chloride hydrochloride (7.63 g, 48.3 mmol), and 18-crown-6 (catalytic amount). The mixture was refluxed for 18 hours, solvent removed in vacuo, then redissolved in dichloromethane and 1 M potassium chloride (40 ml each). The aqueous phase was isolated and extracted twice with 30 ml portions of dichloromethane. The combined organic fraction was washed with saturated sodium chloride (˜50 ml), dried over sodium sulfate, filtered, and dried in vacuo. The crude product was purified via silica gel chromatography, using a 10:1 ratio of silica gel A, 200-425 mesh, and eluting with 5% methanol in chloroform, yielding 1.15 g (15%) pure product.
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