With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.173035-10-4,1,3-Dimesityl-4,5-dihydro-1H-imidazol-3-ium chloride,as a common compound, the synthetic route is as follows.
Potassium 3-fluoronaphtho[1,8-cd][1,2,6]oxadiphosphinine-1(3H)-thiolate 1,3-disulfide (0.108 g,0.30 mmol) was dissolved in degassed water (10 mL). To this solution was added dropwise an equivalent amount of 1,3-dimesityl-4,5-dihydro-1H-imidazol-3-ium chloride (0.102 g, 0.30 mmol) in water (10 mL). The precipitation was almost immediately formed and the mixture was allowed to continue stirring for 2 h. The precipitate was harvested by filtration and dissolved in dichloromethane(30 mL). The solution was dried over MgSO4 and dried in vacuo to give the title compound 15 as white foam (0.175 g, 93%). Selected IR (KBr, cm-1): 1628 (vs), 1481 (m), 1378 (m), 1261 (s), 1217 (m),1162 (m), 942 (s), 904 (m), 849 (m), 82 5(m), 769 (m), 691 (s), 643 (s), 585 (s). 1H-NMR (CD2Cl2, delta),8.61 (s, 2H, Ar-H), 8.32-7.34 (m, 6H, Ar-H), 7.00 (s, 2H, Ar-H), 4.49 (s, 1H, imidazol-H), 3.66 (t, 2H,CH2), 2.36 (s, 12H, CH3), 2.32 (s, 6H, CH3), 1.80 (t, 3H, CH2) ppm. 13C-NMR (CD2Cl2, delta), 159.7(imidazol-C ), 140.9 (Ar-C), 135.1 (Ar-C), 134.6 (Ar-C), 34.2 (Ar-C), 134.0 (Ar-C), 131.7 (Ar-C), 131.5(Ar-C), 130.3 (Ar-C), 130.1 (Ar-C), 129.6 (Ar-C), 126.5 (Ar-C), 126.3 (Ar-C), 125.1 (Ar-C), 124.9(Ar-C), 53.1 (imidazol-C), 51.8 (imidazol-C), 20.9 (CH3), 17.9 (CH3) ppm. 31P-NMR (CD2Cl2, delta),106.4 (d, 2J(P,P) = 54.0 Hz), 78.2 (dd, J(P,F) = 1101 Hz, 2J(P,P) = 54.0 Hz) pm. 19F-NMR (CD2Cl2, delta),-28.7 (dd, 1J(F,P) = 1100 Hz, 3J(P,F) = 3.3 Hz) ppm. MS (CI+, m/z), 307 [C21H27N2]+. Accurate massmeasurement (CI+MS): 307.2170 [C21H27N2]+, calculated mass for [C21H27N2]+: 307.2169; MS (CI-,m/z), 319 [C10H7FOP2S3]-. Accurate mass measurement (CI-MS): 318.9031 [C10H7FOP2S3]-, calculated mass for [C10H7FOP2S3]-: 318.9040.
173035-10-4 1,3-Dimesityl-4,5-dihydro-1H-imidazol-3-ium chloride 2734917, achiral-catalyst compound, is more and more widely used in various.
Reference£º
Article; Hua, Guoxiong; Du, Junyi; Surgenor, Brian A.; Slawin, Alexandra M. Z.; Woollins, J. Derek; Molecules; vol. 20; 7; (2015); p. 12175 – 12197;,
Chiral Catalysts
Chiral catalysts – SlideShare