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| | Ethyl 2-amino-4-thiazoleacetate Basic information |
| | Ethyl 2-amino-4-thiazoleacetate Chemical Properties |
| Melting point | 92-94 °C (lit.) | | Boiling point | 318.5±17.0 °C(Predicted) | | density | 1.2900 (rough estimate) | | refractive index | 1.5400 (estimate) | | Fp | 185 °C | | storage temp. | Keep in dark place,Sealed in dry,Room Temperature | | solubility | soluble in Methanol | | pka | 3.72±0.10(Predicted) | | form | Crystalline Powder | | color | Slightly yellow to beige | | BRN | 139617 | | InChI | InChI=1S/C7H10N2O2S/c1-2-11-6(10)3-5-4-12-7(8)9-5/h4H,2-3H2,1H3,(H2,8,9) | | InChIKey | SHQNGLYXRFCPGZ-UHFFFAOYSA-N | | SMILES | S1C=C(CC(OCC)=O)N=C1N | | CAS DataBase Reference | 53266-94-7(CAS DataBase Reference) |
| Hazard Codes | Xi,Xn | | Risk Statements | 36/37/38-22 | | Safety Statements | 37/39-26-36 | | WGK Germany | 3 | | F | 23 | | HazardClass | IRRITANT | | HS Code | 29349990 | | Storage Class | 11 - Combustible Solids |
| | Ethyl 2-amino-4-thiazoleacetate Usage And Synthesis |
| Chemical Properties | slightly yellow to beige crystalline powder | | Uses | Ethyl 2-Amino-4-thiazoleacetate, is a versatile building block for the synthesis of various pharmaceutical and biologically active compounds including inhibitors and antibiotics. It is used in the synthesis of Cefdinir (C242675) derivatives. | | General Description | Ethyl 2-aminothiazole-4-acetate is an organic ligand and possess strong coordination ability and display diverse coordination modes due to the presence of N, O coordination atoms. | | Synthesis | Thionyl chloride (0.460 mL, 6.321 mmol, 2 eq.) was slowly added to a stirred mixed solution of 2-aminothiazole-4-acetic acid (500 mg, 3.2 mmol) with ethanol (5 mL) at 0 °C. The reaction mixture gradually became clarified, followed by continuous stirring at room temperature for 16 hours. Upon completion of the reaction, the solvent was removed by distillation under reduced pressure to give the crude product. For further purification, two solvent exchanges with ethanol were carried out. The final brown oily product ethyl 2-amino-4-thiazoleacetate was obtained in quantitative yield (588 mg). The product was characterized by NMR hydrogen spectroscopy (400 MHz, DMSO-d6): δ 1.17 (3H, broad peak), 3.72 (2H, broad peak), 4.08 (2H, broad peak), 6.68 (1H, broad peak), 9.43 (2H, broad peak). The resulting compounds can be used directly in the subsequent reaction without further purification. | | References | [1] Patent: WO2014/153667, 2014, A1. Location in patent: Page/Page column 78; 79
[2] Patent: CN106045937, 2016, A. Location in patent: Paragraph 0018; 0022; 0026
[3] Journal of Medicinal Chemistry, 1993, vol. 36, # 24, p. 3843 - 3848
[4] Journal of Agricultural and Food Chemistry, 2006, vol. 54, # 13, p. 4499 - 4505
[5] Tetrahedron Letters, 2000, vol. 41, # 52, p. 10313 - 10317 |
| | Ethyl 2-amino-4-thiazoleacetate Preparation Products And Raw materials |
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