|
|
| | Ethyl acetimidate hydrochloride Basic information |
| | Ethyl acetimidate hydrochloride Chemical Properties |
| Melting point | 112-114 °C(lit.) | | storage temp. | Inert atmosphere,Room Temperature | | solubility | water: soluble50mg/mL, clear, colorless | | form | Crystalline Powder | | color | White | | Water Solubility | Soluble in water (50mg/L). | | Sensitive | Moisture Sensitive | | BRN | 3552401 | | Stability: | Hygroscopic, Moisture Sensitive | | InChI | InChI=1S/C4H9NO.ClH/c1-3-6-4(2)5;/h5H,3H2,1-2H3;1H | | InChIKey | WGMHMVLZFAJNOT-UHFFFAOYSA-N | | SMILES | O(CC)C(=N)C.Cl | | CAS DataBase Reference | 2208-07-3(CAS DataBase Reference) | | EPA Substance Registry System | Ethanimidic acid, ethyl ester, hydrochloride (2208-07-3) |
| Hazard Codes | Xi | | Risk Statements | 36/37/38 | | Safety Statements | 26-36-37/39 | | WGK Germany | 3 | | F | 3-10-21 | | TSCA | TSCA listed | | HazardClass | IRRITANT | | HS Code | 29252900 | | Storage Class | 11 - Combustible Solids |
| | Ethyl acetimidate hydrochloride Usage And Synthesis |
| Chemical Properties | white to light yellow crystal powder | | Uses | Ethyl acetimidate hydrochloride was used in preparation of amidinated carbonic anhydrase via chemical modification of human erythrocyte carbonic anhydrase. It was also used in synthesis of methyl 2-methyl-2-thiazoline-4-carboxylate hydrochloride. | | Synthesis | 2) Example 1-2: Preparation of ethyl acetimidate hydrochloride
1.6 kg of acetonitrile and 4.3 kg of ethanol were added to the reactor and the reactor was cooled to -10°C. 3.67 kg of acetyl chloride was slowly added under stirring and the reaction mixture was kept stirred at 0°C for 12 hours. After completion of the reaction, the solvent was removed by distillation under reduced pressure at 45°C. To the residue was added 11.8 kg of tert-butyl methyl ether and stirred at room temperature for 3 hours. The precipitated solid was collected by filtration and dried under vacuum at 40 °C to give 4.58 kg ethyl acetimidate hydrochloride (yield: 95%).
Product characterization data: 1H-NMR (400 MHz, DMSO-d6) δ: 11.7 (s, 2H), 4.26 (q, 2H), 2.38 (s, 3H), 1.36 (t, 3H). | | Purification Methods | Recrystallise the hydrochloride by dissolving it in the minimum volume of super dry EtOH and adding dry Et2O or from dry Et2O. Dry it in a vacuum and store it in a vacuum desiccator with P2O5. Alternatively it could be crystallised from EtOH (containing a couple of drops of ethanolic HCl) and adding dry Et2O. Filter and dry it in a vacuum desiccator over H2SO4 and NaOH. [Pinner Chem Ber 16 1654 1883, Glickman & Cope J Am Chem Soc 67 1020 1945, Chaplin & Hunter J Chem Soc 1118 1937, McElvain & Schroeder J Am Chem Soc 71 40 1949, McElvain & Tate J Am Chem Soc 73 2233 1951, Methods Enzymol 25 585 1972, Beilstein 2 III 418.] | | References | [1] Combinatorial Chemistry and High Throughput Screening, 2011, vol. 14, # 2, p. 132 - 137
[2] Patent: WO2015/5615, 2015, A1. Location in patent: Paragraph 142; 143; 144
[3] New Journal of Chemistry, 2018, vol. 42, # 16, p. 13367 - 13374
[4] Journal of Medicinal Chemistry, 2004, vol. 47, # 4, p. 915 - 927
[5] Chemische Berichte, 1985, vol. 118, # 8, p. 3089 - 3104 |
| | Ethyl acetimidate hydrochloride Preparation Products And Raw materials |
|