ChemicalBook CAS DataBase List 1-Methyl-1H-imidazole-2-carboxylic acid

1-Methyl-1H-imidazole-2-carboxylic acid synthesis

4synthesis methods

Product Name:1-Methyl-1H-imidazole-2-carboxylic acid
CAS Number:20485-43-2
Molecular formula:C5H6N2O2
Molecular Weight:126.11

13750-81-7

20485-43-2

The general procedure for the synthesis of 1-methyl-1H-imidazole-2-carboxylic acid from 1-methyl-1H-imidazole-2-carboxaldehyde is as follows: first, 1-methyl-1H-imidazole-2-carboxaldehyde was prepared by referring to the method described in literature [23]. Subsequently, the synthetic procedure for Im2COOH (1b) was followed, and the reaction yield was up to quantitative levels after removal of water under high vacuum (without diethyl ether/water washing). Note that heating may cause decarboxylation to occur. Product yield: 100%. Melting point range is 99-101 °C. NMR hydrogen spectrum (400MHz, D2O): δH 7.42, 7.39 (2H, single peak, imidazolium cyclic-H), 4.08 ppm (3H, single peak, N-CH3); NMR carbon spectrum (400MHz, D2O): δC 158.67, 139.68, 125.83, 118.46, 36.73 ppm. infrared spectrum ( KBr press method): ν 3347 (medium intensity), 3119 (medium intensity), 2663 (weak), 1641 (strong), 1683 (medium intensity), 1507 (strong), 1449 (medium intensity), 1388 (strong), 1338 (strong), 1285 (strong), 1173 (medium intensity), 1123 (strong), 961 (medium intensity), 910 (medium), 776 (strong), 685 (strong) cm-1. Calculated values from elemental analysis (C5H8N2O3, molecular weight 144.12): C, 41.67%; H, 5.59%; N, 19.44%. Measured values: C, 41.28%; H, 5.23%; N, 19.12%.

13750-81-7 Synthesis

13750-81-7
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20485-43-2
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$19.00/250mg

Yield:20485-43-2 100%

Reaction Conditions:

with dihydrogen peroxide in water at 20; for 72 h;

Steps:

MeIm2COOH (1c)
First, 1-methylimidazole-2-carboxaldehyde was prepared according to the literature procedure[23]. The synthesis procedure then followed that of Im2COOH (1b) above and the yield was also quantitative after the removal of water under high vacuum (no washing with diethylether/water was necessary). Note: heating causes decarboxylation. Yield: 100%. Mp=99-101°C. δ_H (400MHz, D₂O): 7.42, 7.39 (2H, s, Im-H) and 4.08ppm (3H, s, NCH₃); δ_C (400MHz, D₂O): 158.67, 139.68, 125.83, 118.46, 36.73ppm. IR ν (KBr): 3347(m) 3119(m), 2663(w), 1641(s), 1683(m), 1507(s), 1449(m), 1388(s), 1338(s), 1285(s), 1173(m), 1123(s), 961(m) 910(m), 776(s), 685(s) cm^-1. Anal. Calc. for C₅H₈N₂O₃ (144.12); C, 41.67; H, 5.59; N, 19.44%. Found: C, 41.28; H, 5.23; N, 19.12%.

References:

Gundhla, Isaac Z.;Walmsley, Ryan S.;Ugirinema, Vital;Mnonopi, Nandipha O.;Hosten, Eric;Betz, Richard;Frost, Carminita L.;Tshentu, Zenixole R. [Journal of Inorganic Biochemistry,2015,vol. 145,p. 11 - 18]

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30148-21-1 Synthesis