ChemicalBook CAS DataBase List 2-Aminoimidazole

2-Aminoimidazole synthesis

7synthesis methods

Product Name:2-Aminoimidazole
CAS Number:7720-39-0
Molecular formula:C3H5N3
Molecular Weight:83.09

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22483-09-6 Synthesis

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Yield:7720-39-0 74.9%

Reaction Conditions:

Stage #1:2-methyl-isourea;2,2-dimethoxyethylamine in water at 20 - 50; for 6 h;Inert atmosphere;
Stage #2: with hydrogenchloride in water at 90; for 10 h;Inert atmosphere;

Steps:

Synthesis of 2-amino-1H-imidazole hemisulfate (1)
2Aminoacetaldehyde dimethyl acetal (11.12 mL, 100 mmol) wasdissolved in 50 mL water and o-methylisourea hemisulfate(12.5 g, 100 mmol) was added, and then stirred for 1 h at roomtemperature. The mixture was heated to reach 50 C and kept for5 h to obtain a light yellow solution. The 10 mL of concentrated hydrochloric acid was subsequently introduced into the reactionsolution, and then the reaction liquid was warmed to 90 C andstirred for 10 h. The mixture was evaporated and dissolved in themixed solution of ethanol and water (volume ratio, 1:1), and thesulfate salt crystallized under minus 20 C elsius (9.89 g,74.85 mmol, 74.9%). 1H NMR (D2O, d, ppm): 6.73 (s, 2H, CH).13C NMR (D2O, d, ppm): 146.55, 112.83.

References:

Li, Yanqing;Cheng, Hailong;Xiao, Ru;Cai, Zhengguo [Journal of Catalysis,2020,vol. 383,p. 117 - 123]

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