ClC1C=C(N2C(C)=NC(S)=N2)C=CC=1Cl.C(=O)([O-])[O-].[K+].[K+].Cl.ClCC[N:26]1[CH2:31][CH2:30][O:29][CH2:28][CH2:27]1.[C:32]([OH:37])(=[O:36])[C:33]([OH:35])=[O:34]>CO.O.CCOCC.CCOC(C)=O>[C:32]([OH:37])(=[O:36])[C:33]([OH:35])=[O:34].[NH:26]1[CH2:31][CH2:30][O:29][CH2:28][CH2:27]1
1-(3,4-dichlorophenyl)-5-methyl-1H-1,2,4-triazole-3-thiol (0.4 mmol) was dissolved in methanol (100 mL) at room temperature. A solution of potassium carbonate in water was added dropwise until pH 9. After 15 min. under stirring a solution of 4-(2-chloroethyl)morpholine hydrochloride (0.4 mmol) in water (20 mL) was added. The reaction was left under stirring at room temperature overnight. The methanol was evaporated and after extraction with CH2Cl2 the organic layer was dried over magnesium sulphate then evaporated and finally purified by chromatographic column to give a dark orange oil. The purified product was dissolved in ether (20 mL) and mixed with a solution of oxalic acid (0.31 mmol) in EtOAc (5 mL) to give 4-(2-(3,4-dichlorophenyl)-5-methyl-1H-1,2,4-triazole-3-ylthio)ethyl)morpholine oxalate (0.147 g, yield=84%) as a white precipitate which was filtered off and dried in vacuo. H1NMR (300 MHz, DMSO, 25° C.) δ: 7.93 (d, J=2.4 Hz, 1H); 7.82 (d, J=8.7 Hz, 1H); 7.61 (dd, J=2.4 Hz, J=8.6 Hz, 1H); 3.66 (t, J=4.6 Hz, 4H); 3.32 (t, J=6.8 Hz, 2H); 2.983 (t, J=7.0 Hz, 2H); 2.78 (brs, 4H); 2.47 (s, 3H) ppm. EM (ES+) m/z=373 (100%) [M+H]+. C17H20Cl2N4O5S (463.0) calc. C, 44.07%; H, 4.35%; N, 12.09%; S=6.92%. found C, 43.79%; H, 4.60%; N, 11.87%; S=6.75%.
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