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CAS No. : | 117320-66-8 | MDL No. : | MFCD01940466 |
Formula : | C8H7ClN4S | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | - |
M.W : | 226.69 | Pubchem ID : | - |
Synonyms : |
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Signal Word: | Class: | ||
Precautionary Statements: | UN#: | ||
Hazard Statements: | Packing Group: |
* 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 |
---|---|---|
With pyridine for 4h; Heating; Yield given; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
68% | Stage #1: carbon disulfide; 3-chlorobenzhydrazide With potassium hydroxide In methanol at 20℃; Stage #2: With hydrazine hydrate In water Reflux; Stage #3: With hydrogenchloride In water | |
Stage #1: carbon disulfide; 3-chlorobenzhydrazide With potassium hydroxide In ethanol at 20℃; Stage #2: With hydrazine hydrate In water Reflux; | ||
Stage #1: carbon disulfide; 3-chlorobenzhydrazide With potassium hydroxide In ethanol at 0 - 5℃; for 2h; Stage #2: With hydrazine hydrate In ethanol for 4h; Reflux; Stage #3: With hydrogenchloride In ethanol; water at 20℃; | 4.1.2. General procedure for the synthesis of 4-amino-5-substituted-2,4-dihydro-3H-1,2,4-triazole-3-thiones (A-D) General procedure: Solid potassium hydroxide (0.015 mol) and appropriate aryl hydrazide (benzhydrazide - for A, 2-chlorobenzhydrazide - for B, 3-chlorobenzhydrazide - for C, 4-chlorobenzhydrazide - for D) (0.01 mol) were dissolved in anhydrous ethanol (25 mL) and the resulted solution was cooled to 0-5 °C. Then carbon disulfide (CS2, 1 mL) was added dropwise and the reaction mixture was stirred for 2 min. The precipitated solid of potassium dithiocarbazinate was filtered off, washed with diethyl ether and dried. Thus obtained (in quantitative yield) potassium salt was used in the next step without further purification. A solution of potassium dithiocarbazinate and 80% hydrazine hydrate (10 mL) was refluxed for 4 h, cooled to room temperature, diluted with water (50 mL) and acidified with 3 M HCl. The resulting solids of compounds A-D were filtered, dried and crystallized from anhydrous ethanol. Physicochemical/spectral properties of compounds A-D were described earlier [16], [17], [18], [19], [20], [21] and [22]. |
Stage #1: carbon disulfide; 3-chlorobenzhydrazide With potassium hydroxide In methanol at 20℃; for 24h; Stage #2: With hydrazine hydrate Reflux; | General synthetic procedure for the key intermediates 2 General procedure: The hydrazide 1 was stirred with KOH in absolute methanol and carbon disulfide (CS2) was slowly added. The mixture was stirred 24h at room temperature and the white solid was precipitated, dried. The solid was refluxed with 85% hydrazine monohydrate to obtain the intermediate 2. The crude product was purified by silica gel column chromatography DCM/methanol (40:1). |