Alternatived Products of [ 1874-38-0 ]
Product Details of [ 1874-38-0 ]
CAS No. : | 1874-38-0 |
MDL No. : | MFCD00085149 |
Formula : |
C14H9N3O3
|
Boiling Point : |
- |
Linear Structure Formula : | - |
InChI Key : | - |
M.W : |
267.24
|
Pubchem ID : | - |
Synonyms : |
|
Safety of [ 1874-38-0 ]
Signal Word: | |
Class: | |
Precautionary Statements: | |
UN#: | |
Hazard Statements: | |
Packing Group: | |
Application In Synthesis of [ 1874-38-0 ]
* 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.
- Downstream synthetic route of [ 1874-38-0 ]
- 1
-
[ 99-61-6 ]
-
[ 613-94-5 ]
-
[ 1874-38-0 ]
Yield | Reaction Conditions | Operation in experiment |
86% |
Stage #1: 3-nitro-benzaldehyde; benzoic acid hydrazide In N,N-dimethyl-formamide at 60℃; Inert atmosphere;
Stage #2: With N-ethyl-N,N-diisopropylamine; eosin y In N,N-dimethyl-formamide at 20℃; for 20h; Irradiation; Inert atmosphere; |
General Procedure for the synthesis of 2,5-disubtituted 1,3,4-oxadiazoles 3 from aldehydes and acylhydrazides
General procedure: Asolution of an aldehyde 1 (1.0 mmol)and an acylhydrazide 2 (1.0 mmol) inDMF (3 mL) was heated at 60 oCfor 2-4 h to form the corresponding acylhydrazone (as monitored by TLC). Then,eosin Y (2.0 mol%) and iPr2NEt (2.0 equiv.) were addedand the mixture was irradiated with green LEDs (2.6 W, 161 lm) with stirringunder an air atmosphere at rt for 12-20 h. After completion of the reaction(monitored by TLC), water (5 mL) was added and the mixture was extracted withEtOAc (3 × 5 mL). The combined organic phase was dried over MgSO4,filtered and evaporated under reduced pressure. The resulting product waspurified by silica gel column chromatography using a gradient mixture ofhexane/ethyl acetate as eluent to afford an analytically pure sample of 3. All the products are known compoundsand were characterized by the comparison of their spectral data with thosereported in the literature |
85% |
With 1,4-bis(triphenylphosphonium)-2-butene peroxodisulfate; silica gel for 0.416667h; Microwave irradiation; Green chemistry; |
General Procedure for the one-pot Synthesis of 1,3,4-Oxadiazoles
General procedure: The mixture of acyl hydrazide (1 mmol), aromatic aldehyde (1 mmol), BTPPDS (1 mmol) and silica gel (3g) were finely ground with a mortar and pestle. The mixture was then subjected to microwave irradiation in an open Pyrex beaker for 25 min at 450W. Cold water (5 mL) was added and the mixture was extracted with dichloromethane. The combined organic layers solution was dried over MgSO4. The solvent was concentrated in vacuo; the resulting product was recrystallized from dichloromethane to give the desired product (Table 1). |
75% |
With 1,4-bis(triphenylphosphonium)-2-butene peroxodisulfate In chloroform for 12h; Reflux; |
|
45% |
In dichloromethane for 11h; Heating; |
|
|
Multi-step reaction with 2 steps
1: 6H(1+)*Mo9O40PV3(6-) / acetic acid / 1.33 h / Reflux
2: chromium(VI) oxide / acetic acid / Reflux |
|
|
Multi-step reaction with 2 steps
1: ethanol / Heating
2: sodium chlorate; platinum / methanol / 3.75 h / 20 °C / Electrochemical reaction |
|
|
Multi-step reaction with 2 steps
1: ethanol / Reflux
2: potassium carbonate; iodine / dimethyl sulfoxide / 100 °C |
|
Reference:
[1]Yadav, Arvind K.; Yadav, Lal Dhar S.
[Tetrahedron Letters, 2014, vol. 55, # 13, p. 2065 - 2069]
[2]Gorjizadeh, Maryam; Afshari, Mozhgan; Nazari, Simin
[Oriental Journal of Chemistry, 2013, vol. 29, # 4, p. 1627 - 1630]
[3]Location in patent: experimental part
Badri, Rashid; Gorjizadeh, Maryam
[Phosphorus, Sulfur and Silicon and the Related Elements, 2010, vol. 185, # 3, p. 544 - 549]
[4]Dabiri, Minoo; Salehi, Peyman; Baghbanzadeh, Mostafa; Bahramnejad, Mahboobeh
[Tetrahedron Letters, 2006, vol. 47, # 39, p. 6983 - 6986]
[5]Heravi, Majid M.; Zadsirjan, Vahideh; Bakhtiari, Khadijeh; Bamoharram, Fatemeh F.
[Synthesis and Reactivity in Inorganic, Metal-Organic, and Nano-Metal Chemistry, 2013, vol. 43, # 3, p. 259 - 263]
[6]Singh, Sushma; Sharma, Laxmi Kant; Saraswat, Apoorv; Siddiqui, Ibadur R.; Kehri, Harbans K.; Singh, Rana K. Pal
[RSC Advances, 2013, vol. 3, # 13, p. 4237 - 4245]
[7]Yu, Wenquan; Huang, Gang; Zhang, Yueteng; Liu, Hongxu; Dong, Lihong; Yu, Xuejun; Li, Yujiang; Chang, Junbiao
[Journal of Organic Chemistry, 2013, vol. 78, # 20, p. 10337 - 10343]
- 2
-
[ 610-34-4 ]
-
[ 1874-38-0 ]
Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 3 steps
1: 86 percent / ethanol / 1 h / Heating
2: anhydrous sodium carbonate, dimethylformamide / xylene / 2 h / below 100 deg C
3: 69 percent / thionyl chloride, pyridine / 1 h / Heating |
|
- 3
-
[ 618-94-0 ]
-
trialkyl orthobenzoate
[ No CAS ]
-
[ 1874-38-0 ]
Yield | Reaction Conditions | Operation in experiment |
90% |
With Al3+-K10 montmorillonite clay; In neat (no solvent); at 55℃; for 0.25h;Microwave irradiation; |
General procedure: A 5 mL microwave vial was charged with acidhydrazide (100 mg, 1 eq), trimethyl orthoester (2 eq) and Al3+-K10 clay (75 mg). The resulting mixture was kept under microwave irradiation maintaining the temperature at 55 C for 15 min (Microwave irradiations were performed on CEM-discover model No. 908010). The reaction was monitored by TLC. After completion of the reaction, reaction mixture was diluted with ethyl acetate stirred well, filtered, washed well with ethyl acetate. Filtrate was evaporated under reduced pressure to obtain highly pure product. In some cases, products were purified by column chromatography using 60-120 mesh silica with 20-100 % ethyl acetate in pet ether as eluting solvents. The catalyst recovered by filtration was reused for another 5 more times. |