A common compound: 705-09-9, name is 2-(Difluoromethyl)-1H-benzo[d]imidazole, belongs to imidazoles-derivatives compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below. 705-09-9
A mixture of 2-difluoromethyl-lH-benzimidazole (7.57 g), 2,4-dichloro-6-morpholinopyrimidine (11.7 g), sodium bicarbonate (21 g) and DMF (100 ml) was stirred under nitrogen and heated to 110C for 20 hours. The resultant mixture was cooled, filtered and the filtrate was evaporated. The resultant product was purified by column chromatography on silica using increasingly polar mixtures of ethyl acetate and methylene chloride as eluent. The solid so obtained was a mixture of major and minor isomeric products. The solid was washed with a mixture of isohexane (400 ml) and diethyl ether (400 ml). The washings were evaporated to give a Residue [A]. The washed solid was recrystallised from warm methylene chloride (30 ml) by the addition of isohexane (120 ml). The resultant crystalline solid was isolated and washed with a mixture of diethyl ether (300 ml) and isohexane (300 ml) and the washings were again evaporated to give a Residue [B]. Residues [A] and [B] were combined and purified using a Waters ‘Xterra’ preparative reversed-phase column (5 microns silica, 19 mm diameter, 100 mm length) using decreasingly polar mixtures of water [containing 1% aqueous ammonium hydroxide (d = 0.88)] and acetonitrile as eluent. There was thus obtained a sample of the minor isomeric product, namely 2-chloro- 4-(2-difluoromethylbenzimidazol-l-yl)-6-morpholinopyrimidine (0.173 g); NMR Spectrum: (DMSOd6) 3.73 (s, 8H), 7.2 (s, IH), 7.44-7.52 (m, 2H), 7.51 (t, IH), 7.77-7.79 (m. IH), 7.88-7.90 (m, IH); Mass Spectrum: M+H+ 366.
In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 705-09-9, other downstream synthetic routes, hurry up and to see.
Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; BUTTERWORTH, Sam; GRIFFEN, Edward, Jolyon; PASS, Martin; WO2008/32060; (2008); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem