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CAS No. : | 72760-85-1 | MDL No. : | MFCD00052745 |
Formula : | C5H6N4S | Boiling Point : | No data available |
Linear Structure Formula : | - | InChI Key : | IUVUVQGOSHLPJV-UHFFFAOYSA-N |
M.W : | 154.19 | Pubchem ID : | 736200 |
Synonyms : |
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Signal Word: | Warning | Class: | |
Precautionary Statements: | P280-P305+P351+P338 | UN#: | |
Hazard Statements: | H302 | Packing Group: | |
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 |
---|---|---|
85% | With hydrazine hydrate; In ethanol;Cooling with ice; Reflux; | [Bis(methylsulfanyl)methylene]malononitrile (10 g) was added to a solution of hydrazine monohydrate (4.5 g) in ethanol (10 ml) under ice-cooling. After stirred at room temperature for 30 minutes and refluxed at 80C for one hour, water was added dropwise to the reaction solution under ice-cooling. The precipitated solid was separated by filtration and dried to obtain 5-amino-3-(methylsulfanyl)-1H-pyrazole-4-carbonitrile (colorless solid) (7.6 g, 85%). MS(ESI):155(M+H)+,153(M-H)- 1H NMR(600MHz,DMSO-D6)δppm 2.44(s,3H),6.47(bs,2H), 12.00(bs,1H) |
With hydrazine hydrate; In methanol; at 50℃; for 5h; | General procedure: 2-(Bis(ethylthio)methylene)malononitrile (46, 120 g, 0.605 mol)was dissolved in methanol (1 L). The solution was allowed to stir at rt.To the stirred solution was added hydrazine hydrate (35.3 mL,726 mmol) dropwise over 1 h. Upon completion of addition, the reactionmixture was allowed to stir at 50 C for 4 h before cooling to rt, atwhich time the reaction was complete. Solvent was removed underreduced pressure to afford the product 47 (100 g, quant.) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
20%; 5%; 45% | With triethylamine; In ethanol; at 50℃; for 3h; | General procedure: A solution of 1a-d (1.0 mmol) and 2a (1.0 mmol) was stirred with gentle heating at 50 C in dry ethanol containing 0.5 mL triethylamine till consumption of starting materials. After reaction completion, the solvent was removed und vacuum and the residue was subjected to PLC using toluene/EtOAc (10:1) to give different zones. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65%; 20% | With triethylamine; In ethanol; at 50℃; | General procedure: A solution of 1a-d (1.0 mmol) and 2a (1.0 mmol) was stirred with gentle heating at 50 C in dry ethanol containing 0.5 mL triethylamine till consumption of starting materials. After reaction completion, the solvent was removed und vacuum and the residue was subjected to PLC using toluene/EtOAc (10:1) to give different zones. |