2-Chloro-1H-imidazole

ChEBI: An imidazole compound having a chloro substituent at the 2-position.

2-chloroimidazole is an imidazole compound having a chloro substituent at the 2-position. It is a conjugate base of a 2-chloroimidazolium ion.

Reference Example 1Examples of the imidazole compounds will be given below, which by no means limit them: ... 4-(2-aminoethyl)imidazole 2, 4-dimethylimidazole, and To a solution of B'-1 (2.05g, 20.0 mmol), B'-2 (3.38 g, 20.0mmol), Pd2(dba)3 (0.18g, 0.2mmol), PtBu3 (0.04g, 0.4mmol) and KOtBu (1.44g , 15.0 mmol) were dissolved in 40 ml of toluene, and the mixture was stirred at 80 C for 4 hours. The reaction mixture was cooled to room temperature, and extracted three times with 50 mL of water and 30 mL of diethyl ether. The combined organic layer was dried over MgSO4 and the solvent was evaporated. The resulting residue was purified by silica column method to obtain Intermediate B-1 (3.86 g, yield 82%)General procedure: To a 20 ml or 40 ml viale quipped with a stir bar was added photocatalyst, nitrogen nucleophile, iodomesitylene dicarboxylate, copper salt, and ligand. Dioxane was added followed by addition of the base. The solution was sonicated for 1-3 min until it became homogeneous. Next, the solution was degassed by sparging with nitrogen for 5-10 min before sealing with Parafilm. The reaction was stirred and irradiated using two 34-W blue LED lamps (3 cm away, with cooling fan to keep the reaction at room temperature) for 1 h. The reaction mixture was removed from the light, cooled to ambient temperature, diluted with water (15 ml) and ethyl acetate (25 ml), and the aqueous layer was extracted with ethyl acetate (3 × 25 ml). The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated. The residue was purified by flash chromatography on silica gel to afford the desired decarboxylative C-N coupling product. For aniline substrates, a solution of these nitrogen nucleophiles in dioxane was used; additionally, if the iodomesitylene dicarboxylate is a liquid, its solution in dioxane was used.General procedure: The general procedure described by Pan et.al. ADDIN EN.CITE He201353[46]535317He, PanDu, YufengWang, ShuzhanCao, ChangshengWang, XiaojunPang, GuangshengShi, YanhuiSynthesis, Structure, and Reactivity of Ferrocenyl-NHC Palladium ComplexesZeitschrift fuer anorganische und allgemeine ChemieZeitschrift fuer anorganische und allgemeine Chemie1004-1010639620131521-3749[1] was used to synthesize ferrocenyl(2-methyl imidazole). Briefly, ferrocenemethanol (1 mM) and 2-methyl-1H-imidazole (1.1 mM) were refluxed in acetic acid for 9 hrs at 60 C. The reaction was monitored on preparative TLC. The product was neutralized with 50% KOH in distilled water to remove the acetic acid. The residue was chromatographed on a packed column with CH2Cl2/MeOH (4:1) eluent.

Molecular Weight:102.52
XLogP3:1
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:1
Exact Mass:101.9984758
Monoisotopic Mass:101.9984758
Topological Polar Surface Area:28.7
Heavy Atom Count:6
Complexity:48.1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes