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With thionyl chloride In diethyl ether; 4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran
Synthesis of 2-(Chloromethyl)-1-methyl-1H-imidazole Hydrochloride (BB7) To a solution of (BB6) (35.5 g, 316.96 mmol) in DCM (1500 mL) was added SOCl2 (330 mL, 4436 mmol) at 0° C. The reaction was warmed to ambient temperature and stirred for 5 h. The reaction mixture was concentrated, the residue was washed with DCM (2*500 mL), followed by Et2O (2*200 mL) to obtain (BB7) (50 g, 95percent) as an off-white solid. Rf: 0.4 (EtOAc). 1H NMR (400 MHz, DMSO-d6): δ 7.76 (1H, app d), 7.70 (1H, app d), 5.17 (2H, s), 3.87 (3H, s); ink 131 (MH)+.
88%
Cooling with ice; Reflux
1-Methyl-2-hydroxymethyl imidazole (15.0 g, 134 mmol) was added, with shaking and exclusion of moisture, over a period of 15 min to ice cooled thionyl dichloride (24.6 mL, 30 g, 0.25 mol). The reactants were then heated under reflux for 15 min. The cooled solution was evaporated under reduced pressure followed by recrystallization from ethanol (25 mL) and dried under high vacuum to give 2-(chloromethy1)-1-methyl-1H-imidazole hydrochloride as brown crystals. Yield: 15.1g, 88percent. 1H NMR (CDCl3) δ ppm: 7.79 (s, 1H), 7.70 (s, 1H), 5.2 (s, 2H), 3.86 (s, 3H). 3C NMR (CD3OD) δ ppm: 142.05, 124.7, 119.08, 33.9, 31.4. TOF-MS m/z: 131.0384 (M+H+, 100percent). Molecular formula of cation, C5H7N2Cl, calculated m/z of cation: 131.04 (M+H+)
78%
Stage #1: at 0℃; for 0.5 h; Reflux; Inert atmosphere Stage #2: With hydrogenchloride In water
This compound was synthesised using a modified procedure described in literature.6 1-Methyl-2-hydroxymethyl imidazole (6.500 g, 58.000 mmol) was added in small portions to SOCl2 (12.7 mL, 174 mol) at 0 °C. The mixture was heated under reflux for 30 min. After cooling, the solution was concentrated under reduced pressure followed by recrystallization from ethanol (17 mL) to afford 2-(chloromethy1)-1-methyl-1H-imidazole hydrochloride. Yellow crystals; 7.580g, yield: 78percent. The NMR spectrum was according to literature.61H NMR (CDCl3) δ = 7.79 (d, 1H, J = 1.9 Hz; ImH), 7.70 (d, 1H, J = 1.9 Hz; ImH), 5.20 (s, 2H; CH2Cl), 3.86 ppm (s, 3H; NCH3).
Reference：
[1] Patent: US2012/322722, 2012, A1,
[2] Tetrahedron Letters, 2011, vol. 52, # 41, p. 5308 - 5310
[3] Tetrahedron, 1996, vol. 52, # 48, p. 15171 - 15188
[4] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1993, # 19, p. 2291 - 2302
[5] Tetrahedron Letters, 2013, vol. 54, # 45, p. 6087 - 6089
[6] Organic and Biomolecular Chemistry, 2009, vol. 7, # 2, p. 229 - 231
[7] Patent: US6646122, 2003, B1, . Location in patent: Page/Page column 10
[8] Patent: EP1422228, 2004, A1, . Location in patent: Page 228
[9] Patent: EP1724263, 2006, A1, . Location in patent: Page/Page column 29
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