Category: 104-98-3

Related Products of 104-98-3, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 104-98-3, name is 3-(1H-Imidazol-4-yl)acrylic acid belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Step 1: Palladium on carbon (lO%, 150 g, 1.41 mol) was added to a solution of urocanic acid (1, 1.01 kg, 7.33 mol) in MeOH (5.50 L), water (5.50 L) and 35% HCI (752mL, 8.59 mol) and the resulting mixture was hydrogenated at normal pressure for 4 days. Conversion of the reaction was monitored by 1H NMR. The catalyst was filtered off after completion and the filtrate was evaporated to dryness. The residue was re-dissolved in MeOH (7.00 L) and 2.2 M solution of HCI in MeOH (500 mL) was added and stirred for 16 hours at 45 C. The solvents were removed by evaporation to dryness. MeOH (10.0 L)and HCI (47.0 g) in MeOH (1.00 L) were added and stirred overnight at 45 C. The mixture was evaporated to dryness to give pure 3-(1H-imidazol-4-yl)-propionic acid methyl ester hydrochloride (2) as off-white solid. Yield: 1.37 kg (98%). 1H NMR (300 MHz, MeOD-d4) o 7.40-7.28 (m, 10 H); 7.19-7.07 (m, 6 H); 6.55 (s, 1 H); 3.63 (s, 3 H); 2.94-2.83 (m, 2 H); 2.71-2.62 (m, 2 H).

The synthetic route of 3-(1H-Imidazol-4-yl)acrylic acid has been constantly updated, and we look forward to future research findings.

104-98-3, A common heterocyclic compound, 104-98-3, name is 3-(1H-Imidazol-4-yl)acrylic acid, molecular formula is C6H6N2O2, 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.

Urocanic acid (32) (4.74 g, 34.33 mmol), amine 33 (5.5 g, 34.33 mmol) and HOBt (5.26 g, 34.33 mmol) were suspended/dissolved in DMF (50 mL) and the mixture was cooled to 0 C. N-(3-Dimethylaminopropyl)-N’-ethylcarbodiimide hydrochloride (6.91 g, 36.05 mmol) was added and the mixture was slowly warmed to rt and stirred overnight (The suspension turned to a clear orange solution after 2 h). The mixture was diluted with 2.5% aq NaOH (500 mL) and brine (100 mL). Repeated treatment with EtOAc (12 * 200 mL) afforded an extraction of product 34 only in low amounts and extraction with CHCl3 (2 * 150 mL) failed as well. Therefore, the aqueous phase was concentrated under reduced pressure at 40 C to a volume of 300 mL and then treated twice with CHCl3/MeOH 5:1 (500 and 400 mL). The organic phases were combined with the earlier EtOAc and CHCl3 extracts and removal of the volatiles under reduced pressure yielded a yellow liquid (ca 50 mL). DMF was removed under reduced pressure (50 C, 10 mbar) and the residue was subjected to column chromatography (eluent: CH2Cl2/MeOH 50:1 to 10:1). Removal of the solvent from the eluate under reduced pressure, uptake in CH2Cl2 (80 mL), evaporation, uptake in CH2Cl2 (50 mL) followed by removal of the solvent in vacuo afforded 34 as a white powder (8.27 g, 86%), mp 159-161 C. A minor fraction was recrystallized from acetone/EtOAc to yield colorless needles, mp 165-167 C. Rf = 0.6 (CH2Cl2/MeOH 5:1). Anal. calcd for C13H20N4O3: C, 55.70; H, 7.19; N, 19.99; found: C, 55.65; H, 7.29; N, 19.86. IR (Nujol) 3355, 3300, 1685, 1665, 1630, 1530 cm-1. 1H NMR (400 MHz, CD3OD) delta (ppm) 1.46 (s, 9H), 3.23 (t, 2H, J 6.2 Hz), 3.39 (t, 2H, J 6.2 Hz), 6.52 (d, 1H, J 15.6 Hz), 7.36 (s, 1H), 7.46 (d, 1H, J 15.6 Hz), 7.77 (s, 1H). 13C NMR (100 MHz, CD3OD) delta (ppm) 29.6, 41.5, 42.0, 81.0, 120.1, 123.2 (br), 133.1, 137.5 (br), 139.2, 159.4, 170.2. MS (ESI, MeOH) m/z (%) 583 (76) [2M+Na]+, 319 (38) [M+K]+, 303 (100) [M+Na]+, 281 (17) [M+H]+, 203 (26) [M-C4H8-CO2+Na]+, 181 (22) [M-C4H8-CO2+H]+, C13H20N4O3 (280.32).

The synthetic route of 104-98-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Keller, Max; Traenkle, Christian; She, Xueke; Pegoli, Andrea; Bernhardt, Guenther; Buschauer, Armin; Read, Roger W.; Bioorganic and Medicinal Chemistry; vol. 23; 14; (2015); p. 3970 – 3990;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem