Application of 4857-06-1, These common heterocyclic compound, 4857-06-1, name is 2-Chloro-1H-benzo[d]imidazole, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.
Scheme 1Intermediate A1 : 2-Chloro-1-(tetrahvdropyran-2-yl)-1 H-benzimidazoleA 10 I reactor is charged under argon and with stirring with 2.5 I of THF, 180 g of 2- chlorobenzimidazole (1.18 mol) and 325 ml of 3,4-dihydro-2H-pyran (6.56 mol, 3 eq.). The reactor is heated until dissolution takes place (temperature of the medium: 40C). Then 6.3 g of para-toluenesulphonic acid (0.033 mol, 0.028 eq.) are introduced. The temperature is maintained at between 49 and 52C for 2.5 hours. The system is cooled to 12C and 7.65 g of sodium methoxide (0.142 mol, 0.12 eq.) are added, with stirring maintained, over a total time of 15 minutes. The temperature is then brought to 18C, 5 I of n-heptane are added, and the whole is filtered over 300 g of Clarcel FLO-M, the retentate being washed with 5 I of n- heptane. The filtrate is concentrated to dryness under reduced pressure to give 292.6 g of 2- chloro-1-(tetrahydropyran-2-yl)-1 H-benzimidazole in the form of a slightly yellow oil (quantitative yield). 1H NMR (400 MHz, DMSO-d6): 1.42 to 2.01 (m, 5H); 2.21 to 2.34 (m, 1 H); 3.69 to 3.78 (m, 1 H); 4.12 (d, J=1 1.4 Hz, 1 H); 5.72 (dd, J=2.4 and 1 1.2 Hz, 1 H); 7.22 to 7.34 (m, 2H); 7.62 (d, J=7.2 Hz, 1 H); 7.78 (d, J=7.2 Hz, 1 H).
The synthetic route of 4857-06-1 has been constantly updated, and we look forward to future research findings.
Reference:
Patent; SANOFI; AROKIASSAMY, Nathalie; BILLOT, Pascal; CARRY, Jean-Christophe; CLAVIERES, Patrick; CLERC, Francois; CROCQ – STUERGA, Veronique; LACHAUD, Sylvette; LIENARD, Philippe; MENEGOTTO, Jerome; SCHIO, Laurent; WO2012/66486; (2012); A1;,
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