ChemicalBook CAS DataBase List 2-amino-1,5-dihydro-4H-imidazol-4-one

2-amino-1,5-dihydro-4H-imidazol-4-one synthesis

4synthesis methods

Product Name:2-amino-1,5-dihydro-4H-imidazol-4-one
CAS Number:503-86-6
Molecular formula:C3H5N3O
Molecular Weight:99.09

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Yield: 49%

Reaction Conditions:

with hydrogenchloride in water at 120; for 22 h;Heating;

Steps:

The synthesis of polyandrocarpamines A & B (PAC1 and PAC2) was performed from corresponding benzaldehyde derivatives, n-propylamine and 2-aminoimidazolin-4-one, the preparation of which was previously described in literature [53] (Figure 5). Guanidine (2.95 mmol, 1eq) and HClaq 6N (9 mL) were heated at 120 °C for 22 h. Water was removed under vacuum and the crude product was solubilized in hot ethanol (9 mL). Diethylether (6 mL) was added, then the mixture was cooled to 0 °C. After 6 h, filtration was performed and the 2-aminoimidazolin-4-one was isolated as a white powder with a 49% yield. RMN 1H (D2O): δ 4.18 (s, 2H, H-1); RMN 13C (D2O):δ 48.5 (C-1); 174.9 (C=O); [M - HCl]+ = 99.0427 (99.0433 C3H5N3O); F = 200-202 °C. PAC1 and PAC2 were then produced by mixing the corresponding benzaldehyde (vanillin or catechaldehyde 1.48mmol, 1 eq) with n-propylamine (2.95 mmol, 2 eq). The imine formation was performed under microwave irradiation at 60 °C for 30 min (maximized authorized power 60 W). Acetonitrile was added to the crude imine with 2-aminoimidazolin-4-one (1.48 mmol, 1 eq), and the mixture was stirred at reflux for 63 h. The solvent was removed under reduced pressure.

References:

Loaëc, Nadège;Attanasio, Eletta;Villiers, Beno t;Durieu, Emilie;Tahtouh, Tania;Cam, Morgane;Davis, Rohan A.;Alencar, Aline;Roué, Mélanie;Bourguet-Kondracki, Marie-Lise;Proksch, Peter;Limanton, Emmanuelle;Guiheneuf, Solène;Carreaux, Fran ois;Bazureau, Jean-Pierre;Klautau, Michelle;Meijer, Laurent [Marine Drugs,2017,vol. 15,# 10,art. no. 316]