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CAS No. : | 4755-77-5 | MDL No. : | MFCD00000706 |
Formula : | C4H5ClO3 | Boiling Point : | - |
Linear Structure Formula : | C2H5OC(O)C(O)Cl | InChI Key : | OWZFULPEVHKEKS-UHFFFAOYSA-N |
M.W : | 136.53 | Pubchem ID : | 20884 |
Synonyms : |
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Signal Word: | Danger | Class: | 8,3 |
Precautionary Statements: | P280-P305+P351+P338-P310 | UN#: | 2920 |
Hazard Statements: | H226-H314 | Packing Group: | Ⅱ |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
24% | at 70℃; for 5 h; | Step 1 ethyl 5-amino-l,3,4-thiadiazole-2-carboxylate To a solution of hydrazinecarbothioamide (10 g, 54.8 mmol) in POCI3 (25 mL) was added ethyl 2-chloro-2-oxacetate (6.1 mL, 54.8 mmol). The reaction was heated to 70°C and stirred for 5 h. POCI3 was completely removed from the reaction mixture under vacuum. The residue was diluted with ice cold water (150 mL) and basified to pH 8 with saturated sodium bicarbonate solution and then extracted with ethyl acetate (200 mL). The organic layer was separated and dried over a2S04, and the solvent was evaporated to obtain crude product. The crude product was purified by flash chromatography (silica gel 100-200?, 2percent methanol and dichloromethane) to afford ethyl 5-amino-l,3,4-thiadiazole-2-carboxylate as a yellow solid (3.1 g, 24percent yield). ? NMR (400 MHz, DMSO-d6): ? 7.94 (s, 2H), 4.29 (q, 2H), 1.27 (t, 3H); LC- MS m/z calcd for [M+H]+ 174.03, found 174.1. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
51% | With triethylamine In dichloromethane | Example 2 Ii; Compound 4 was prepared according to the Ref: J. Hetero. Chem. 1995, 32, 1693-1702. Then, it was reduced by NaBH4ZLiCl in ethanol solution. Further oxidation by Dess-Martin reagent gave the desired aldehyde 6 in 25 percent overall two-step yield. |