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Chemical Structure| 34296-51-0

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Product Details of [ 34296-51-0 ]

CAS No. :34296-51-0
Formula : C9H7N3O
M.W : 173.17
SMILES Code : O=CC1=CN(C2=CC=CC=C2)N=N1
MDL No. :MFCD00100219

Safety of [ 34296-51-0 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P330-P332+P313-P337+P313-P362-P403+P233-P405-P501

Application In Synthesis of [ 34296-51-0 ]

* 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 [ 34296-51-0 ]

[ 34296-51-0 ] Synthesis Path-Downstream   1~3

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  • [ 34296-51-0 ]
  • [ 103755-58-4 ]
  • [ 4600-04-8 ]
  • 2
  • [ 103755-58-4 ]
  • [ 34296-51-0 ]
YieldReaction ConditionsOperation in experiment
99% With manganese(IV) oxide; In dichloromethane; at 20℃; Step 2 Synthesis of 1-Phenyl-1H-[1,2,3]triazole-4-carbaldehyde MnO2 (1.23 g, 14.14 mmol) was added to a stirred solution of <strong>[103755-58-4](1-phenyl-1H-[1,2,3]triazol-4-yl)-methanol</strong> (245 mg, 1.4 mmol) in DCM (15 mL) and the resulting mixture was stirred at room temperature overnight. The mixture was filtered over a celite bed, and the filtrate was concentrated under reduced pressure to afford 271 mg (99%) of 1-phenyl-1H-[1,2,3]triazole-4-carbaldehyde.
78% With pyridinium chlorochromate; In dichloromethane; at 20℃; for 1.5h; A solution of 8.75 g (0.05 mol) of <strong>[103755-58-4](1-phenyl-1H-1,2,3-triazol-4-yl)methanol</strong> (11) in 100 mL of methylene chloride was added in one portion with thorough stirring to a suspension of 16.15 g (0.075 mol) of freshly prepared pyridinium chlorochromate (PCC) in 200 mL of anhydrous methylene chloride. The mixture was stirred for 90 min at room temperature, 200 mL of anhydrous diethyl ether was added, the solution was separated from the black precipitate by decanting, and the precipitate was washed with diethyl ether (2 × 50 mL). The combined extracts were filtered through 20 g of silica gel, the solvent was distilled off under reduced pressure, and the residue was recrys-tallized from carbon tetrachloride. Yield 6.75 g (78%). mp 96-97C. 1 H NMR spectrum (500 MHz, DMSO-d 6 ), delta, ppm: 7.57 t (1H, p-H, J = 7.2 Hz), 7.65 t (2H, m-H, J = 7.2 Hz), 8.03 d (2H, o-H, J = 7.2 Hz), 9.59 s (1H, 5-H), 10.24 s (1H, CHO). Mass spectrum: m/z 174 [M + H] + . Found, %: C 62.45; H 4.14; N 24.21. C 9 H 7 N 3 O. Calculated, %: C 62.42; H 4.07; N 24.27.
With manganese(IV) oxide; In dichloromethane; at 20℃; for 72h; Step b: Preparation of l-phenyl-lH-l,2,3-triazole-4-carbaldehyde (9). To a solution of (1- phenyl-lH-l,2,3-triazol-4-yl)methanol, 7, (1.03 g, 5.87 mmol) in CH2Cl2 (50 mL) was added MnO2 (2.05g, 23.5 mmol). The reaction mixture was stirred for 3 days at room temperature. The reaction mixture was then filtered through Celite and the resulting filtrate was concentrated in vacuo. The crude material was purified by silica gel chromatography (0-5% methanol/dichloromethane) yielding 0.83g (82%) of 9: 1H NMR (400 MHz, CDCl3) delta 10.22 (s, IH), 8.51 (s, IH), 7.53, (d, J= 9.6 Hz, 2H), 7.58-7.49, (m, 3H).
With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In dimethyl sulfoxide; at 20℃; for 4h; General procedure: Into a round-bottom flask equipped with a magnetic stirring bar already containing a solution of 10mmolof 1,2,3-triazoles type 12 in 27.5mL of DMSO was added 11mmolof IBX. This mixture was stirred at room temperature for 4h. Next, distilled water (20mL) was added, and stirring was continued for 15minat room temperature. Subsequently, the mixture was filtered, extracted with ethyl acetate and dried over with MgSO4. The product was purified via silica-gel column chromatography using gradient mixture of hexane-ethyl acetate to afford the pure derivatives 11 and 15a-b.
With Jones reagent; In acetone; at 0℃; for 0.583333h; General procedure: The 1-substituted-1,2,3-triazol-4-yl-methanol 1 (4mmol) was taken in dry acetone (10mL), cooled to 0C and the Jones reagent (CrO3+H2SO4+Acetone) (4mmol) was added slowly over a period of 15min. The reaction mixture was stirred for 20min at 0C. After completion of reaction, filtered through the short pad of celite and the filtrate was collected and concentrated under vacuum. The residue was purified by passing through a column packed with silica gel using petroleum ether/EtOAc (8:2) as eluents.
With chromium(VI) oxide; acetic acid; In water; at 100℃; for 1h; General procedure: Propynyl alcohol (2.2 g, 0.04 mol), cuprous iodide (0.4 g, 2.0 mmol) andN,N-diisopropylethylamine (5.2 g, 0.04 mol) were sequentially added into a stirred solution of intermediate9a-9l(0.04 mol) in absolute ethanol (10 v/w) at 25oCfor 24 h. The insoluble matter removed by filtration, and the filtrate is concentrated. Next the filtrate was poured into water, extracted with dichloromethane, and the combined organic layer was washed with water, dried over anhydrous Na2SO4and evaporated to dryness to give compounds10a-10l. Intermediate10a-10l(0.10 mol) without purification was dissolved in glacial acetic acid (10 v/w), chromium trioxide (2 mL, 0.01 mol) was added dropwise and the mixture was stirred 1 h at 100oC.After cooling to r.t., solvent was removed by concentrate under reduced pressure. The residue was added to water under stirring, the precipitates were collected by filtration and washed with water to obtain compounds11a-11l.

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[2]Archiv der Pharmazie,2015,vol. 348,p. 796 - 807.
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  • 3
  • [ 34296-51-0 ]
  • [ 57497-39-9 ]
  • [ 1613039-81-8 ]
YieldReaction ConditionsOperation in experiment
89% With sodium hydrogencarbonate; In ethanol; at 60℃; General procedure: A mixture of 1-substituted-1H-1,2,3-triazole-4-carbaldehyde 2 (1mmol), N-benzyl/t-butyl hydroxylamine hydrochloride (1.5mmol) and sodium bicarbonate (1.5mmol) in absolute ethanol (6mL) was heated at 60°C until the carbonyl compound was disappeared (monitored by TLC). The solvent was removed in vacuo and the reaction mixture was diluted with H2O and extracted with EtOAc. Combined organic layers dried over anhydrous sodium sulfate and concentrated. The residue was purified by column chromatography (SiO2, mixtures of petroleum ether/EtOAc).
89% With sodium hydrogencarbonate; In ethanol;Reflux; General procedure: A mixture of the corresponding 1-substituted-1H-1,2,3-triazole-4-carbaldehyde (1 equiv), N-alkylhydroxylamine hydrochloride (1.5 equiv) and sodium bicarbonate (1.5 equiv) in absolute ethanol (6 mL/mmol) as solvent was heated to reflux until the aldehyde consumed (after 2-3 hours checked by TLC). The reaction mixture was brought to room temperature and ethanol was removed under reduced pressure. The residue was diluted with water and the product was extracted with ethyl acetate. The organic layers were combined and the solvent was removed under reduced pressure. The crude product was purified by column chromatography (SiO2, eluted in petroleum ether/EtOAc).
 

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