2-(2-Aminothiazole-4-yl)-2-hydroxyiminoacetic acid synthesis
- Product Name:2-(2-Aminothiazole-4-yl)-2-hydroxyiminoacetic acid
- CAS Number:66338-96-3
- Molecular formula:C5H5N3O3S
- Molecular Weight:187.18
68401-22-9
66338-96-3
GENERAL METHOD: NaOH (2.4 g, 0.06 mol) was dissolved in water (100 mL) and stirred under cooling in an ice bath. To this solution was added ethyl 2-(2-aminothiazol-4-yl)-2-(trans)-hydroxyiminoacetate or ethyl 2-(2-aminothiazol-4-yl)-2-(cis)-hydroxyiminoacetate (10.76 g, 0.05 mol). The reaction mixture was stirred at 15-20°C for 2-3 hours. After completion of the reaction, the solvent was removed by distillation under reduced pressure. The residual solid was dissolved in water (100 mL), decolorized by the addition of Norit (1.0 g) and filtered. Glacial acetic acid was slowly added dropwise to the filtrate under stirring until the pH reached neutral. The resulting precipitate was collected by filtration, washed with water and finally the product was purified by two ethanol recrystallizations.
![Ethanamine, N-[(3,5-dichlorophenyl)methylene]-2,2-diethoxy-](/CAS/20210305/GIF/1000210-73-0.gif)
1000210-73-0
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66338-96-3
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Yield: 71%
Reaction Conditions:
with sodium hydroxide in water at 15 - 20;
Steps:
2.2.1 2-(2-Aminothiazole-4-yl)-2-(anti)-hydroxyiminoacetic acid (anti-A) and 2-(2-aminothiazole-4-yl)-2-(syn)-hydroxyiminoacetic acid (syn-A)
General procedure: To a solution of NaOH (2.4g, 0.06mol) in water (100mL) was added ethyl 2-(2-aminothiazole-4-yl)-2-(anti)-hydroxyiminoacetate [22] or ethyl 2-(2-aminothiazole-4-yl)-2-(syn)-hydroxyiminoacetate [23] (10.76g, 0.05mol) with stirring in an ice bath. The mixture was stirred for 2-3h at 15-20°C, after that the solvent was removed in vacuum. The solid residue was dissolved in H2 (100mL), treated with Norit (1.0g) and filtered. The glacial acetic acid was added dropwise to the filtrate with stirring till neutral reaction. The resulting precipitate was filtered off, washed with water and recrystallized twice from the ethanol.
References:
Orysyk;Zholob;Bon;Nikulina;Orysyk;Nikolaienko;Garmanchuk;Zborovskii, Yu.L.;Tolstanova;Khranovska;Pekhnyo;Vovk [Polyhedron,2015,vol. 85,p. 208 - 220]
64485-82-1
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66338-96-3
119 suppliers
$15.00/1g