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ChemicalBook CAS DataBase List 1-Methyl-2-imidazolidinethione

1-Methyl-2-imidazolidinethione synthesis

6synthesis methods
-

Yield: 55%

Reaction Conditions:

in ethanol;water at 110;Cooling with ice;

Steps:

1) 1-Methyl-imidazolidine-2-thione (imdzSH-Me)
Carbon disulfide (0.6 ml, 9.95 mmol) was added dropwise to a cooled (ice bath) solution of 1-methylethylenediamine (3.8 g, 51 mmol) in ethanol (9 ml) and water (9 ml). A white precipitate was formed. The reaction mixture was heated at 60°C and a further quantity of carbon disulfide (3 ml, 49.7 mmol) was added. The precipitate initially dissolved but shortly after a large amount of white solid precipitated out. The reaction mixture was heated under reflux (110°C) for 1 h and conc. HCl (0.5 ml) was added. The mixture was heated under reflux for a further 10 h. The reaction mixture was cooled and stored in a freezer. The resulting precipitate was filtered off and washed with cold acetone to give the desired ligand (Yield, 55%). Anal. Calcd for C4H8N2S (%): C, 41.3; H, 7.7; N, 24.1; S, 27.6; Found: C, 41.1; H, 7.5; N, 23.7; S, 26.5. Main IR peaks (KBr, cm-1): (NH) 3196(m); (CH) 2945(w), 2872(w); (CN) + (C-H) 1512(s), 1480(m), (C=S) 1200(s); (N-CH3) 958(s). 1H NMR data (CDCl3, ppm): 5.7 sb (1H, NH), 3.72 m (2H, C4H), 3.57 m (2H, C5H), 3.15 s (3H, CH3). 1-Ethyl-imidazolidine-2-thione (imdzSH-Et), n-propyl-imidazolidine-2-thione (imdzSH-Prn), n-butyl-imidazolidine-2-thione (imdzSH-Bun) were preapred by the same method.

References:

Lobana, Tarlok S.;Sultana, Razia;Butcher, Ray J.;Jasinski, Jerry P.;Golen, James A.;Castineiras, Alfonso;Pröpper, Kevin;Fernandez, Francisco J.;Vega, M. Cristina [Journal of Organometallic Chemistry,2013,vol. 745-746,p. 460 - 469] Location in patent:supporting information

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