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CAS No. : | 79491-05-7 | MDL No. : | MFCD00102267 |
Formula : | C9H9N3O2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | HHMLQRYQRQDWTA-UHFFFAOYSA-N |
M.W : | 191.19 | Pubchem ID : | 4329732 |
Synonyms : |
|
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P280-P305+P351+P338-P304+P340 | UN#: | N/A |
Hazard Statements: | H302 | 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 |
---|---|---|
With dinitrogen tetraoxide; sodium sulfate In dichloromethane at 0℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | With potassium etoxide In ethanol for 5h; Heating; | |
79% | With potassium hydroxide In lithium hydroxide monohydrate at 80℃; for 2h; | |
In lithium hydroxide monohydrate for 2h; |
With potassium hydroxide In lithium hydroxide monohydrate for 5h; Reflux; | General procedure for the synthesis of 4-substituted-urazoles General procedure: Amine (3 mmol) and cesium carbonate (3.5 mmol) was dissolved in anhydrous 1,4-dioxane (10mL). Triphosgene (1 mmol) was added in portions over 2-3 min and this mixture was stirred atroom temperature. After 1.5 hour ethyl carbazate (3.2 mmol) was added and reaction mixturewas stirred overnight. Following evaporation to dryness, the reaction mixture was refluxed inaqueous 5 M KOH for 5 hours then it was cooled down in an ice bath. The solution wasneutralized with concentrated HCl to reach to a pH of 1-2. The white crystalline product wascollected and dried to give the corresponding urazole (Table 1). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | With potassium hydroxide for 0.75h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
28% | Stage #1: chloroformic acid ethyl ester; <i>p</i>-toluidine With triethylamine In acetone at 0℃; for 1h; Stage #2: ethylhydrazine carboxylate With triethylamine In acetone for 10h; Heating; Further stages.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 71 percent / tetrahydrofuran / 8 h / Heating 2: 92 percent / sodium ethoxide / ethanol / 5 h / Heating | ||
Multi-step reaction with 3 steps 1: Et3N / toluene / 8 h / Heating 2: toluene / 8 h / 25 °C 3: 92 percent / sodium ethoxide / ethanol / 5 h / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 94 percent / Et3N / tetrahydrofuran; CH2Cl2 / 2 h / 0 - 25 °C 2: 71 percent / tetrahydrofuran / 8 h / Heating 3: 92 percent / sodium ethoxide / ethanol / 5 h / Heating | ||
Multi-step reaction with 4 steps 1: 94 percent / Et3N / tetrahydrofuran; CH2Cl2 / 2 h / 0 - 25 °C 2: Et3N / toluene / 8 h / Heating 3: toluene / 8 h / 25 °C 4: 92 percent / sodium ethoxide / ethanol / 5 h / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: toluene / 8 h / 25 °C 2: 92 percent / sodium ethoxide / ethanol / 5 h / Heating | ||
Multi-step reaction with 2 steps 1: benzene / 20-25 deg C, 2 h; reflux, 2 h 2: KOH / H2O / 2 h | ||
Multi-step reaction with 2 steps 1: 98 percent / benzene / 0.33 h 2: 60 percent / 4M aq. KOH / 0.75 h / Heating |
Multi-step reaction with 2 steps 1: 1,4-dioxane / 20 °C 2: potassium hydroxide / lithium hydroxide monohydrate / 5 h / Reflux | ||
Multi-step reaction with 2 steps 1: acetonitrile; toluene / 14 h / 20 °C / Reflux 2: potassium hydroxide / lithium hydroxide monohydrate / 2 h / 80 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: N-bromosuccinimide / CH2Cl2 / 0.33 h / 0 °C 2: 28 mg / chlorobenzene / 3 h / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: N-bromosuccinimide / CH2Cl2 / 0.33 h / 0 °C 2: 32 mg / chlorobenzene / 2 h / 110 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 93 percent / NBS / CH2Cl2 / 1 h / 0 °C 2: 76 percent / benzene / 5 h / Ambient temperature |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 93 percent / NBS / CH2Cl2 / 1 h / 0 °C 2: 82 percent / benzene / 5 h / Ambient temperature |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 93 percent / NBS / CH2Cl2 / 1 h / 0 °C 2: 86 percent / benzene / 5 h / Ambient temperature |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 93 percent / NBS / CH2Cl2 / 1 h / 0 °C 2: 72 percent / benzene / 5 h / Ambient temperature |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 93 percent / NBS / CH2Cl2 / 1 h / 0 °C 2: 81 percent / benzene / 5 h / Ambient temperature |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: [bis(acetoxy)iodo]benzene / tetrahydrofuran / 0.33 h / 20 °C 2: toluene / 0.5 h / 20 °C 3: pyridine; hydrogen fluoride / tetrahydrofuran |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: [bis(acetoxy)iodo]benzene / tetrahydrofuran / 0.33 h / 20 °C 2: toluene / 0.5 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: [bis(acetoxy)iodo]benzene / tetrahydrofuran / 0.33 h / 20 °C 2: toluene / 0.5 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: [bis(acetoxy)iodo]benzene / tetrahydrofuran / 0.33 h / 20 °C 2: toluene / 0.5 h / 20 °C 3: pyridine; hydrogen fluoride / tetrahydrofuran |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: caesium carbonate / 1,4-dioxane / 1.5 h / 20 °C 2: 1,4-dioxane / 20 °C 3: potassium hydroxide / water / 5 h / Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: toluene; tetrahydrofuran / 20 °C / Inert atmosphere 2: hydrogen fluoride; pyridine / tetrahydrofuran / 20 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In tetrahydrofuran; toluene at 20℃; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: calcium hypochlorite / dichloromethane / 2 h / 20 °C 2: magnesium(II) chloride / dichloromethane / 24 h / 20 °C |