Brief introduction of 16042-25-4

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Synthetic Route of 16042-25-4, A common heterocyclic compound, 16042-25-4, name is 2-Imidazolecarboxylic acid, molecular formula is C4H4N2O2, 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.

To a stirred suspension of 1H-imidazole-2-carboxylic acid (3.00 g, 26.8 mmol) in anh. DCM (45 mL)cooled to 0 C under N2 was added oxalyl chloride (4.5 mL, 53.5 mmol) followed by addition of DMF (2 drops). The reaction was allowed to warm to rt and stir overnight. A further portion of oxalylchloride (1.13 mL, 13.4 mmol) and DMF (1 drop) was added and the reaction stirred for 4 hr.Volatiles were then removed in vacuo and the residual oxalyl chloride was removed by coevaporationwith toluene to afford acid chloride as a colourless solid. The solid was then addedportionwise to conc NH4OH (15 mL) chilled to 0 C. Volatiles were then removed in vacuo.Residual volatiles were coevaporated with toluene to obtain dry material (25: 75 startingmaterial:product). The crude was retreated to the reaction with oxalyl chloride (1.7 mL, 20.1 mmol)using the above procedure. The solid obtained was then washed with water (2 x 20 mL) and driedin vacuo to obtain a tan solid (2.16 g, 73%) that was used without further purification. LCMS (Waters Atlantis: Gradient Method 2): Rt = 1.44 min, 99 A% 254 nm, [M + H]+ = 112.2. 1H NMR(600 MHz, DMSO-d6) delta 12.95 (s, 1H), 7.73 (s, 4H), 7.43 (s, 1H), 7.23 (br s, 1H), 7.04 (br s, 1H).

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Article; Jarrad; Debnath; Miyamoto; Hansford; Pelingon; Butler; Bains; Karoli; Blaskovich; Eckmann; Cooper; European Journal of Medicinal Chemistry; vol. 120; (2016); p. 353 – 362;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem