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CAS No. : | 50270-27-4 | MDL No. : | MFCD02257700 |
Formula : | C5HCl3N2O | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | KVJIRFGNHAAUNQ-UHFFFAOYSA-N |
M.W : | 211.43 | Pubchem ID : | 10932746 |
Synonyms : |
|
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P280-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H332-H335 | Packing Group: | N/A |
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 |
---|---|---|
92% | Step 2. 2,4,6-trichloropyrimidin-5-formonitrile 2,4,6-trichloropyrimidin-5-carboxaldehyde (10 g, 47.4 mmol), hydroxylamine hydrochloride (3.3 g, 47.5 mmol), glacial acetic acid (100 mL), and H2O (5 mL) were added to a 150-mL round-bottom flask, and heated to 60 C. to react for 1 hour. After the completion of the reaction, the reaction solution was poured into crushed ice, and was extracted with CH2Cl2. The resultant organic phases were combined, washed with a saturated NaCl solution, dried with anhydrous Na2SO4, and then filtered and concentrated. The obtained substance was dissolved in SOCl2 (60 mL), reacted at room temperature for 10 minutes, and then heated for a reflux reaction for 2 hours. After the completion of the reaction, the resultant mixture was subjected to reduced pressure distillation to remove SOCl2 to give a residue, which was then dissolved in EtOAc and washed with H2O. The resultant organic phase was dried with anhydrous Na2SO4, filtered, and concentrated to obtain an oily substance of 9 g. The yield was 92%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With triethylamine; In tetrahydrofuran; water; at -78 - -10℃; for 2.5h;Inert atmosphere; | To a solution of 2,4,6-trichloropyrimidine-5-carbaldehyde (3.9 g, 18.5 mmol) in tetrahydrofuran (100 mL) was added dropwise a solution of ethyl 3-hydrazinobenzoate hydrochloride (4.0 g, 18.5 mmol) in tetrahydrofuran/ water (50 mL, v: v = 9: 1) at -78 C under nitrogen atmosphere. Then triethylamine (7.7 mL, 55.4 mmol) was added dropwise and the mixture was stirred at -78 C for 30 minutes under nitrogen atmosphere. Then the mixture was warmed to -10 C and stirred for further 2 h. Upon completion of the reaction, the solvent was removed in vacuo. The residue was purified with silica gel column chromatography (ethyl acetate: petroleum ether = 1: 10) to give 1.01 g of the product (batch contained impurities) as a light yellow solid. MS (ESIpos): m/z = 337 (M+H)+ |
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