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Chemical Structure| 33893-89-9
Chemical Structure| 33893-89-9
Structure of 33893-89-9 * Storage: {[proInfo.prStorage]}
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Product Details of [ 33893-89-9 ]

CAS No. :33893-89-9 MDL No. :MFCD00068114
Formula : C6H5N5 Boiling Point : -
Linear Structure Formula :- InChI Key :LQWXEEDCMLEVHU-UHFFFAOYSA-N
M.W : 147.14 Pubchem ID :320267
Synonyms :

Calculated chemistry of [ 33893-89-9 ]

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 11
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 4.0
Num. H-bond donors : 1.0
Molar Refractivity : 37.41
TPSA : 67.35 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -7.08 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.02
Log Po/w (XLOGP3) : 0.17
Log Po/w (WLOGP) : 0.26
Log Po/w (MLOGP) : 0.2
Log Po/w (SILICOS-IT) : 1.18
Consensus Log Po/w : 0.57

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.56

Water Solubility

Log S (ESOL) : -1.53
Solubility : 4.31 mg/ml ; 0.0293 mol/l
Class : Very soluble
Log S (Ali) : -1.14
Solubility : 10.6 mg/ml ; 0.0721 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.61
Solubility : 0.358 mg/ml ; 0.00243 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.83

Safety of [ 33893-89-9 ]

Signal Word:Danger Class:4.1
Precautionary Statements:P240-P210-P241-P264-P280-P302+P352-P370+P378-P337+P313-P305+P351+P338-P362+P364-P332+P313 UN#:1325
Hazard Statements:H315-H319-H228 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 33893-89-9 ]

* 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 [ 33893-89-9 ]

[ 33893-89-9 ] Synthesis Path-Downstream   1~85

  • 1
  • [ 100-70-9 ]
  • [ 33893-89-9 ]
YieldReaction ConditionsOperation in experiment
96% With sodium azide; tetrabutylammomium bromide; at 105℃; for 6h;Sealed tube; Green chemistry; General procedure: A screw capped vial was charged with nitrile (2 mmol), NaN3(2.4 mmol, 1.2 equiv.) and tetrabutylammonium bromide (2.4 mmol,1.2 equiv.). The resulting mixture was stirred at 105 C and monitoredby TLC. After completion of the reaction, the reaction mixture wascooled to room temperature and dissolved with water (5 mL). Then, theaqueous solution was acidified with 1M HCl to pH = 3. If a precipitatewas formed, the suspension was filtered and the filter cake was washedwith water to afford the pure product. Otherwise, the aqueous solutionwas extracted with EtOAc (3 × 4 mL). The organic phase was washedwith 1M HCl (3 × 4 mL), dried with anhydrous Na2SO4, filtered andevaporated under vacuum to afford the pure product.
95% With sodium azide; acetic acid; In butan-1-ol; for 144h;Reflux; 2-Cyanopyridine (10.4 g, 0.1 mol), sodium azide (7.3 g, 0.12 mol),glacial acetic acid (8.0 g, 0.12mol) and butyl alcohol (40 mL)was putinto a reactor. The mixture was heated to reflux for 4 day. Thenadding sodium azide (1.8 g, 0.03 mol), glacial acetic acid (4.0 g,0.06 mol) into reactor again, the reaction continues reacting 2 daysin reflux. After cooling to room temperature, the mixture waspoured into a large amount of water. Then driped hydrochloric acidwith concentrated, until all the crystal precipitation. By filteringand vacuum drying, get white crystal, Yield 95%,1H NMR (600 MHz,Chloroform-d, delta) 13.40 (s, 1H), 8.82 (d, J = 4.9 Hz, 1H), 8.44 (d,J = 7.9 Hz, 1H), 8.01 (t, J = 7.7 Hz, 1H), 7.58-7.54 (m, 1H). Anal. Calcdfor C6H5N5: C, 48.98; H, 3.40; N, 47.62. Found: C, 48.99; H, 3.384; N,47.35.
94% In order to expand the scope of this flow method, a variety of nitriles were subjected to the optimized conditions in the entry 6 (Table 1), and the results are summarized in Tables 3 and 4 {Method A). For substrates 2 and 3, where no electron- donating or electron- withdrawing group was present on the aromatic ring, or substrate 4 where the nitrile was rendered electron poor by the presence of electron- withdrawing group at the para position, the reactions proceeded to 100% conversions without the formation of any side product. Similarly, meta tolunitrile (5) and the hetero aromatic substrates (6-8) also showed excellent conversions. Electron rich nitriles 10 and 10 reacted to give moderate but clean conversions to the corresponding tetrazoles. The biphenyl nitriles 9, 13 and 14 also proved to be good substrates for this reaction regardless of position of the phenolic hydroxy group on the second aromatic ring.Notably, chiral nitrile 15 provided 15a, a derivative of which (no CBZ group) has found utility as an organocatalyst, in > 99% ee and 92% yield based on conversion. To test if an increase in the ¾ can drive the reaction of moderately yielding substrates to completion, the model substrate 1 was reacted at a ¾ of 30 min (Table 4). There was no significant change in the conversion observed; instead a small amount of hydrolysis product la was formed. However, significant improvement in the reaction rate was observed by doubling the concentration of the reaction (0.4 M). For nitrile 1, the conversion increased from 65% to 81% (¾ = 30 min), while similar improvement in conversions were observed for substrates 11 and 13-15 when the reaction concentration was doubled.As this continuous flow method has the advantage of using high temperatures in a safe manner, it was determined that the presence of a catalyst (e.g., ZnBr2) was not essential for all reactions carried out at these temperatures. To test this, the flow process was repeated with selected substrates without the use of ZnBr2 (Tables 3 and 4, Method B). The non- substituted benzo- and napthonitrile substrates (2 and 3), electron poor nitrile (4), and the heterocyclic substrates (6, 7 and 8), all showed excellent conversions to corresponding tetrazoles in the absence of ZnBr2. The conversions were found to decrease moderately in case of biphenyl substrates 9, 13 and 14 indicating decrease in the reaction rate of these substrates in the absence of ZnBr2. Similar decrease in conversion was observed for the electron rich substrates (1 and 12), but it was noted that there was no side product observed in the absence of ZnBr2 even at 30 min of residence time. This shows that ZnBr2 may be promoting the competing side reaction. Thus, the use of ZnBr2 may be useful for enhancing the conversion of the electron-rich nitriles, but can also lead to formation of side product. In many, if not all instances, reactions without ZnBr2 can give clean conversions. To demonstrate the scale-up capabilities of this, the synthesis of 3a was carried out using aUniqsis FlowSyn continuous flow reactor. FlowSyn is an integrated continuous flow reactor system that uses a pair of high pressure pumps to deliver reagent solutions through a 'T'-mixer into the electrically heated flow coil or column reactors. The homogenous solution of reagents ([3] = 1M; [NaN3] = 1.05 M) in NMP:H20 (7:3) was pumped using a single pump through a coiled PFA tubing reactor (volume of heated zone ~ 6.9 mL) with a flow rate of 0.35 mL/min (tr = 20 min) at 190 C (see Example 2). The flow process was run continuously for 2.5 h to obtain 9.7 g of 3a in 96 % yield. This corresponds to a product output of 4.85 g/h or 116 g/day for the tetrazole 3a.Overall, the method performed is a safer alternative for currently used methods to synthesize 5-substituted tetrazoles as the hazards due to accumulation and condensation of HN3 are greatly minimized. Only uses a slight excess of NaN3 (1.05 equiv) was used, and hence the production of azide waste is minimal. The method is highly efficient and clean, and works for a wide range of substrates. In case of substrates where the reaction does not go to completion, the remaining NaN3 in the reaction can be quenched by introducing streams of sodium nitrite and sulfuric acid after the reaction is complete. The incorporation of this quenching procedure increases the overall safety of the process. Therefore, given the widespread applications of tetrazoles in chemical andpharmaceutical industry, this method can serve as a safe and highly efficient alternative for synthesis of tetrazoles.General protocol for continuous flow synthesis of tetrazoles (Method B):Sodium azide (138 mg, 2.1 mmol) was dissolved in 0.5 mL of water and added to the nitrile substrate (2 mmol) dissolved in 4.5 mL of NMP. The resulting solution was filled in a 10 mL stainless steel syringe and the flow process was carried out as described for Method A. The flow process was carried out behind an explosion shield ...
93% With sodium azide; In N,N-dimethyl-formamide; at 110℃; for 4h; General procedure: A mixture of nitrile (1 mmol), sodium azide (1.5 mmol), Cu complex catalyst (0.4 mol%) and DMF (3 mL) was taken in a round-bottomed flask and stirred at 110 C temperature. After completion of the reaction the catalyst was separated from the reaction mixture with an external magnet and reaction mixture was treated with ethyl acetate (2 × 20 mL) and 1 N HCl (20 mL). The resultant organic layer was separated and the aqueous layer was again extracted with ethyl acetate (2 × 15 mL). The combined organic layers were washed with water, concentrated, and the crude material was chromatographed on silica gel (Hexane-EtoAc, 1:1) to afford the pure product.
92% With sodium azide; In water; at 100℃; for 1h;Green chemistry;Catalytic behavior; General procedure: Benzonitrile (1 mmol, 0.103 g), sodium azide (1.1 mmol, 0.0759 g), and 2 mL water were taken in a reaction tube and stirred at room temperature to make homogeneous suspension, and then 20 wt% catalyst (ZnO-RGO) was added to the reaction mixture. The reaction mixture was heated to 100 C for 2 h. The progress of the reaction was monitored by TLC. After completion of the reaction, the reaction mixture was cooled to room temperature and centrifuged. The filtrate was treated with 5N HCl (10 mL) and then with ethyl acetate. The organic layer was separated, washed with deionized water, and then dried over anhydrous sodium sulfate and concentrated to give the crude solid crystalline 5-phenyl-1H-tetrazole. It was recrystallized from n-hexane, ethyl acetate, and the yield was about 0.143 g.
92% With sodium azide; L-proline; In N,N-dimethyl-formamide; at 110℃;Green chemistry; General procedure: The mixture of organic nitrile (1 mmol), NaN3 (1.25 mmol) and L-proline (30 mol%) in DMF (5mL) was stirred at 110 C for 1-2 h. The progress of the reaction was monitored by TLC. Aftercompletion of the reaction, the reaction mixture was allowed to cool to room temperature. Thecooled reaction mixture was poured in ice water (15 mL) with stirring. The resulting mixture wasacidified with dilute HCl under vigorous stirring. The solid product* was filtered under suction,washed with sufficient cold water till free of acid. The product was air dried to obtain the pureproduct.*In cases where solid product was not obtained after acidification, like benzyl cyanide andaliphatic nitriles, the acidified aqueous phase was extracted with ethyl acetate (2 X 20 mL), thecombined organic phase was washed with brine, dried over anhydrous sodium sulfate andconcentrated in vacuo to get the corresponding pure product.
91% With sodium azide; zinc(II) chloride; In propan-1-ol; at 95℃; for 0.5h; General procedure: NaN3 (11.6 mmol) and ZnCl2 (9.7 mmol) were added to a solution of the appropriate nitrile (9.7 mmol) in n-PrOH or n-BuOH (25mL). The temperatures, reaction times and solvents are listed in Table4. Vigorous stirring was essential.
90% With sodium azide; In N,N-dimethyl-formamide; at 120℃; for 6h; General procedure: A mixture of nitrile (1 mmol), sodium azide (1.5 mmol) and catalyst (0.02 g, contains 0.4 mol% of Cu(II)) in DMF (3 mL) was taken in a round-bottomed flask and stirred at 120 C. The progress of the reaction was followed by thin-layer chromatography (TLC). After completion of the reaction, the reaction mixture was cooled to room temperature and diluted with ethyl acetate (3×20 mL). The catalyst was removed by using magnetic field or filtration and then the resulting solution was washed with 1N HCl, dried over anhydrous Na2SO4 and then was evaporated. The crude products were obtained in excellent yields. All products were characterized by 1H, 13C NMR, FT-IR, and melting point which were in agreement with literature. We have reported the spectral data of some aromatic and heteroaromatic synthesized compounds
90% With lithium tetraazidoborate; ammonium acetate; In methanol; N,N-dimethyl-formamide; at 100℃; for 8h; General procedure: NH4OAc (15 mg) was added to a mixture of benzonitrile(103 mg, 1 mmol) and LiB(N3)4(93 mg, 0.5 mmol) in DMF/MeOH (9/1) solution (5 mL) and stirred the mixture was at 100 oC for 8 h. After completion of reaction (monitored by TLC),the mixture was cooled to room temperature and diluted with ethyl acetate. Theresulting solution was washed with 1 M HCl, dried over anhydrous Na2SO4, and concentrated. An aqueous solution of NaOH (1 M) was added to the residue, and the mixture was stirred for 30 min at room temperature. The resulting solution was washed with ethyl acetate, and then 2 MHCl was added until the pH value of the water layer became 1~2. The aqueouslayer was extracted with ethyl acetate three times, and the combined organic layerswere washed with 1M HCl.The organic layer was dried over anhydrous Na2SO4 and concentrated to furnish pure 5-phenyl-1-H-tetrazole 1b as a white solid (125 mg) in 86% yield.
90% With Nano TiO2/SO42-; In N,N-dimethyl-formamide; for 6h;Green chemistry; General procedure: In a round-bottom flask, benzonitrile (1 mmol), sodiumazide (1 mmol), and nano TiO2/SO42 (0.2 g) were charged.Then the reaction mixture was stirred in distilleddimethylformamide (1 mL) at 120 8C. The progress ofthe reaction was followed by TLC (75:25 ethyl acetate:n-hexane). After completion of the reaction, the catalystwas separated by centrifugation, washed with doublydistilled water and acetone, and the centrifugate wastreated with 5 N HCl (20 mL) under vigorous stirring. Theaqueous solution finally obtained was extracted twice with ethyl acetate. The combined organic phase was washedwith water and concentrated to precipitate the crudecrystalline solid. All products were characterized by NMR,IR, mass spectra, and CHN analysis and the data for theknown compounds were found to be identical with theliterature. The complete spectroscopic data are describedin the supporting information. Yield: 90%. White solid. M.p. 208-210 8C (lit. [11] 210-213 8C). 1H-NMR (250 MHz, DMSO-d6): d = 3.93 (brs, 1 H),7.64-7.58 (m, 1 H), 8.03-8.09 (m, 1 H), 8.19 (d, J = 8.76 Hz,1H), 8.74 (d, J = 4.86 Hz, 1 H) ppm. 13C-NMR (62.9 MHz,DMSO-d6): d = 122.7, 126.1, 138.5, 143.3, 149.7, 154.7 ppm.IR (KBr): n = 3417, 2818, 2724, 1623, 1599, 1512, 1384,1350, 1039, 833 cm1.
89% With sodium azide; In N,N-dimethyl-formamide; at 120℃; for 3h; General procedure: A mixture of nitrile (1 mmol), sodium azide (1.5 mmol),catalyst (25 mg), and DMF (3 mL) was taken in a 5 mLround bottomed flask and heated at 120C. After completionof the reaction (observed on TLC) the reactionmixture was cooled to r.t. and separated from catalyst bycentrifugation. The solvent was removed under reducedpressure. The residue was dissolved in water (5 mL) andacidified with HCl (37%). The precipitation was filteredand crystallized in a mixture of water and ethanol. Furtherpurification with column chromatography was notnecessary.2.3 Physical and spectroscopic data for selectedcompounds2.3a 2-(1H-Tetrazole-5-yl)pyridine (2j): White solid;M.p.: 212-214C ; 1H NMR (DMSO-d6, 400 MHz): delta(ppm) = 7.4 (t, J = 6.4 Hz, 1H), 7.8 (t, J = 6.4 Hz,1H), 8.0 (t, J = 8.0 Hz, 1H), 8.5 (d, J = 3.2 Hz,1H) ppm; 13C NMR (DMSO-d6, 100 MHz): delta (ppm)= 167.5, 159.1, 150.0, 139.4, 120.2 ppm; IR (KBr)nu:3278, 3181, 2929, 1662, 1578, 1390, 923 cm-1.
85% With sodium azide; ammonium acetate; In N,N-dimethyl-formamide; at 70℃; for 4h; General procedure: The [AMWCNTs-O-Cu(II)-PhTPY] heterogeneous catalyst was subjected to 5 successive reuses under the reaction conditions: For each reaction, nitrile (1.0mmol), NaN3 (1.3mmol) and NH4OAc (1.0mmol) were mixed and stirred in DMF (1mL) in the presence of 4mol-% of [AMWCNTs-O-Cu(II)-PhTPY] at 70C in an uncapped vial. After the completion of the reaction, as monitored by TLC using n-hexane/ethyl acetate, the mixture was diluted by H2O (5mL), then the mixture was vacuum-filtered onto a sintered-glass funnel, and the residue was consecutively washed with ethyl acetate (30mL), water (5mL). The heterogeneous catalyst was recharged for another reaction run. The combined supernatant and organic washings were extracted with ethyl acetate (3×10mL), the combined organic layer was dried over anhydrous Na2SO4. Removal of the solvent under vacuum, followed by purification on silica gel using hexane/ethyl acetate as the eluent afforded the pure products.
85% With sodium azide; triethylamine hydrochloride; In toluene; at 110℃; for 24h; General procedure: The mixture of the appropriate nitrile (50 mmol), NaN3 (65 mmol),and Et3N·HCl (150 mmol) in toluene (100 mL) was stirred at 110 Cfor 17-30 h (2b, 2f, 2k, and 2l for 24 h; 2c and 2d for 17 h; 2e and2j for 30 h). The mixture was cooled to r.t. and extracted with H2O(100 mL). The aqueous layer was acidified with 36% aq HCl andfiltered. The resultant solid was washed with H2O and dried underreduced pressure.
85% With sodium azide; triethylamine hydrochloride; In toluene; at 110℃; for 24h; General procedure: The mixture of a nitrile (50 mmol), NaN3 (65 mmol) and Et3N.HCl (150 mmol) in toluene (100 mL) was stirred at 110C for 17-30 h(2b, 2fand 2l for 24 h; 2c and 2d for 17 h; 2e and 2j for 30 h) . After cooling to room temperature, the mixture was extracted withwater (100 mL). To the aqueous layer, 36% HCl was added dropwise till pH was acidic. After filtration, the solid was washed withwater and dried under reduced pressure, yielding the expected tetrazoles 2. The corresponding physical and spectroscopic data for alltetrazoles 2 follow.
85% With sodium azide; triethylamine hydrochloride; In toluene; at 110℃; for 24h; General procedure: A mixture of nitrile (50 mmol), NaN3 (65 mmol), and Et3N·HCl (150 mmol) in toluene (100 mL) was stirred at 110 C for 17-30 h (2b, 2f and 2l for 24 h; 2c and 2d for 17 h; 2e and 2j for 30 h). After cooling to r.t., the mixture was extracted with H2O (100 mL). To the aqueous layer, 36% HCl was added dropwise to acidic pH. After filtration, the solid was washed with water and dried under reduced pressure to give the expected tetrazole 2. The corresponding physical and spectroscopic data for tetrazoles 2 are detailed below.
78% With sodium azide; In N,N-dimethyl-formamide; at 120℃; for 16h; General procedure: In a round-bottom flask, 0.2 g benzonitrile (2 mmol) and0.4 g sodium azide (6 mmol), were added to 10 mL DMF.To this mixture, 20 mg of functionalized KIT-6 was addedand the reaction mixture was refluxed. The progress ofreaction was monitored by TLC (75:25 ethyl acetate/nhexane).After completion of the reaction, the reactionmixture was cooled and filtered. The solid materials werewashed three times with acetone and then with the water.The catalyst was collected and dried to activation for nextrun. The product was obtained by acidification of solutionwith hydrochloric acid (5 mL, 6 M). The precipitate wasfiltered and recrystallized from a water/ethanol mixture toget pure product as a white powder, yield: 88%.
74% With sodium azide; zinc(II) chloride; In water; at 95℃; for 2h;Microwave irradiation; 2-(tetrazol-5-yl)pyridine (ttzpH) was synthesized as follows. Into a 35 mL microwave vessel was placed a stir bar, 15 mL of deionized water, 2-cyanopyridine (5 mmol, 0.52g), sodium azide (5.5 mmol, 0.36g) and zinc(II) chloride (5 mmol, 0.68g). The reaction was stirred under the conditions of microwave radiation and the power was adjusted to maintain 95C for two hours. Upon cooling, concentrated hydrochloric acid was added drop wise to the mixture while stirring to adjust the pH to 1. After stirring for one hour, the solid material was filtered, washed with cold water and dried under vacuum. Yield 74%.
73% With sodium azide; ammonium chloride; In N,N-dimethyl-formamide; at 130℃; for 24h; In a round-bottom flask equipped with a condenser, 5.00?g (48.1?mmol) 2-cyanopyridine (17), 9.37?g (144.1?mmol) NaN3, 7.71?g (144.1?mmol) NH4Cl and 20?mL DMF were added, heated to 130?C, and stirred for 24?h. The suspension was cooled to room temperature, poured into 200?mL water/ice, and the pH adjusted to 6 with HCl (10%). The precipitate formed was separated by filtration and recrystallized over water, affording 5.16?g (73%) of colorless crystals. m.p.: 214.4-216.0?C (lit. 213?C) [ 53 ]. 1H NMR (200?MHz, DMSO-d6) delta ppm: 7.55-7.64 (m, 1H, Pyr-H), 8.00-8.09 (m, 1H, Pyr-H), 8.17-8.23 (m, 1H, Pyr-H), 8.72-8.81 (m, 1H, Pyr-H). 13C NMR (50.3?MHz, DMSO-d6) delta ppm: 122.63, 126.10, 138.23, 143.69, 150.06, 154.78.
73% With sodium azide; ammonium chloride; In N,N-dimethyl-formamide; for 24h;Reflux; General procedure: In a typical procedure, 5-aryl-1H-tetrazoles (1-24) were synthesized by adding aryl nitriles (1 eq.), sodium azide (1.2 eq.), and ammonium chloride (1 eq.) in solvent, the mixture was refluxed for 24 h. Progress of the reaction was monitored by thin layer chromatography. After completion of the reaction, 2.5 mL of 2M NaOH was added and the solution was stirred for half an hour. The reaction mixture was concentrated on reduced pressure, and dissolved in water. 3M HCl was added to the reaction mixture until precipitates formed. The precipitates were filtered and washed with distilled water. The yields of title compounds were found to be moderate to high.
65% With hydrogenchloride; sodium azide; triethylamine; In toluene; for 12 - 16h;Reflux; 2-Cyanopyridine (10 mmol) was taken in 300 mL of toluene followed by the addition of sodium azide (130 mmol) and triethylamine (130mmol). Conc. HCl (130 mmol) was added dropwise to this solution and stirred without heating for 0.5 h, reflux the reaction mixture for 12-16 h. Now this reaction mixture was added with 30 mL of water and stirred for another 0.5 h. The aqueous layer was separated from the organic layer and added 100 mmol of acetic acid after few minutes till white crystals are formed
65% With hydrogenchloride; sodium azide; triethylamine; for 12 - 16h;Reflux; 2-Cyanopyridine(10 mmol) in 300 mL of toluene, 130 mmol of sodium azideand 130 mmol of triethylamine were mixed together followedby the addition of 130 mmol of conc. HCl with constant stirringfor 30 min and then refluxed for 12-16 h. Now, addded 30 mLof water and stirred for 30 min resulted in the formation oftwo layers. Separate the aqueous layer by adding 10 to 100 mmolof acetic acid, after few minutes white crystals were obtained[25,26]. Yield (7.5 g, 65 %); .m.w. 147; m.p. 215-220 C.
64% With sodium azide; In dimethyl sulfoxide; at 85℃; for 12h; General procedure: General procedure for the synthesis of Tetrazole. A mixture of benzonitrile (103 mg, 1 mmol), sodium azide (97.5 mg, 1.5 mmol), and 3 mL DMSO solvent was added in a 25 mL round bottomed flask. Further (50 mg, 23 mol %, w/w) catalyst was added to the reaction mixture. The reaction mixture was heated to 85 C for 12 h. After completion of the reaction (as monitored by TLC), the catalyst was separated by simple filtration, washed with diethyl ether and the filtrate was treated with ethyl acetate (30 mL) and 5 N HCl (20 mL) and stirred vigorously. The resultant organic layer was separated and the aqueous layer was again extracted with ethyl acetate (20 mL). The combined organic layers were washed with water and dried over anhydrous sodium sulfate and were evaporated under reduced pressure to give the product. The product was purified by the column chromatography. The structure was confirmed by spectral analysis (1H NMR, mass and elemental analysis).
54% With sodium azide; ammonium chloride; lithium chloride; In N,N-dimethyl-formamide; at 110℃; for 10h; A suspension of 2-cyanopyridine (10 g, 96 mmol), sodium azide (12.5 g,192 mmol), ammonium chloride (10.3 g, 192 mmol) and lithium chloride (2 g, 48 mmol) in anhydrous dimethylformamide (100 mL) was stirred for 10 h at 110 C. The solution was cooled and the insoluble salts were removed by filtration. The solvent was evaporated under reduced pressure and then the residue was dissolved in deionized water (200 mL) and acidified with concentrated HCl (3 mL), to initiate precipitation. The product was removed by filtration, washed with water (30-40 mL) and dried to give a brown solid, which was recrystallized from hot ethanol to give 2 as brown needles, yield: 54 %. m.p.: 221-223 C; 1H NMR (DMSO-d6): 8.56 (d, 1H, J = 7.9 Hz,), 8.0 (d, 1H, J = 7.8 Hz,), 7.79 (t, 1H, J = 7.8 Hz,), 7.26 (t, 1H, J =7.9 Hz,), 7.1 (s, 1H) ppm.
27% With sodium azide; triethylamine hydrochloride; In toluene; at 110℃; General procedure: A mixture of the corresponding nitrile (50 mmol), NaN3 (65 mmol) and Et3N·HCl (150 mmol) in toluene (100 mL) was stirred at 110 C for17-30 h (TLC monitoring). After cooling to r.t., the mixture was extracted with H2O (100 mL) and the aqueous phase was acidified with aq 36% HCl. The solid formed was filtered, washed with H2O (3 × 10mL), and dried under reduced pressure to give the corresponding product 2a-e
With sodium azide; zinc(II) chloride; In N,N-dimethyl-formamide; at 20 - 80℃;Inert atmosphere; The tetrazole derived ligand TP was synthesized according to a literature procedure described as follows [13]. 10 mmol of picolinonitrile and 20 mmol of NaN3 were slowly added into 50 mL of redistilled DMF. Then 1 g of ZnCl2 was added. The solution was firstly stirred at room temperature for 30 min and then heated to 80 C overnight under N2 protection. After cooling, the solution was poured into plenty of crushed ice. The crude product was further purified on a silica gel column (n-hexane:CH2Cl2 = 50:1) to give the desired ligand as white powder. 1H NMR (300 Hz, CDCl3, 25 C): d 7.82 (1H, m), 8.12 (1H, m), 8.32 (1H, d, J = 6.0), 8.83(1H, m). Anal. Calcd for C6H5N5: C, 48.98; H, 3.43; N, 47.60. Found: C, 48.87, H, 3.56; N, 47.56.
10.8 g With sodium azide; ammonium chloride; In water; N,N-dimethyl-formamide; at 137℃; for 65h; 2-Pyridyl carbonitrile (12.5 g, 0.12 mol) was charged to a 2 L, three neck round bottomed flask equipped with condenser with attached N2 inlet-outlet, mechanical stirrer and thermocouple. Solid NH4Cl (6.4 g, 0.12 mol) was added. DMF (880 mL) then water (6.27 g) was added followed by sodium azide (7.8 g, 0.12 mol). The reaction was refluxed at approximately 137 C. overnight. A new very polar spot was seen by TLC but some starting material remained. NaN3 and NH4Cl, (each 0.05 mol/mol, based on the amount of substance of the 2-pyridyl carbonitrile) was added followed by a small amount of water. The reaction was complete after a total of about 65 h at 137 C. The mixture was carefully concentrated to remove DMF (CAUTION; a small amount of azide remains). The residue was dissolved in aqueous Na2CO3 (8 g, 0.075 mol in 0.3 L of aqueous solution). This aqueous layer was washed with ethyl acetate (2×200 mL). The aqueous layer was carefully brought to a pH of from 4 to 5 under good ventilation as traces of hydrazoic acid may form. The solid product (7 g) precipitated out of solution. The pH was then brought to between 1 and 2, and another batch of crystals was collected (3.8 g). These batches were shown to be the same substance by NMR.
With sodium azide; N,N-dimethylammonium chloride; In N,N-dimethyl-formamide; at 110 - 115℃; for 8h; General procedure: Sodium azide, 11.4 mmol, and dimethylamine hydrochloride, 11.2 mmol, were dissolved in 10 mL of DMF, 10 mmol of the corresponding nitrile and 5 mL of DMF were added, and the resulting suspension was heated for 8 h at 110-115C. The mixture was cooled and filtered from the precipitate of sodium chloride, and the precipitate was washed with 10 mL of DMF on a filter. The filtrate was diluted with 30 mL of cold water and acidified with 10% aqueous HCl to pH 2-3. The precipitate was filtered off, thoroughly washed with cold water (3*30 mL), and dried in air. The physical constants and spectral parameters of 3a-3j were in agreement with published data [13, 14].
With sodium azide; In N,N-dimethyl-formamide; at 120℃; General procedure: Nano-Fe3O4(at)TiO2/Cu2O (20 mg) and K4[Fe(CN)6].3H2O (0.09 g, 0.22 mmol), wasadded to a solution of aryl iodide (1 mmol) in distilled DMF (2 mL) and the reactionmixture was stirred under heating at 120 C for the appropriate time to obtain the nitrilecompound. To the nitrile compound generated in situ was added sodium azide (SafetyNote: Sodium azide is highly toxic. All workers should be thoroughly familiar with itssafe use before attempting experiments and proper personal protective gear must beused. 0.1g, 1.5 mmol) and the reaction was continued until the complete conversion ofthe nitrile to the tetrazole during 5 hours. After the completion of the reaction (as monitoredby TLC, 75:25 ethyl acetate: n-hexane), the catalyst was easily separated out fromthe reaction mixture by using an external magnet, washed with acetone, dried in theoven and re-used for a consecutive run under the same reaction conditions. After theseparation of the catalyst the crude material was then taken up in ethyl acetate andwashed with HCl (5 N) and the layers separated. The combined organic layers werethen washed with water and concentrated to obtain the crude product. The crude productwas purified by short column chromatography to obtain the pure products in highyield (see Tables 1 and 2). All the products are known compounds and the spectral dataand melting points were identical to those reported in the literature.
With sodium azide; zinc dibromide; In water; at 100℃; for 8h; L1B. 2-(1H-tetrazol-5-yl)pyridine (L1B) was obtained as follows. Amixture of 2-cyanopyridine (10 mmol), NaN3 (15 mmol), ZnBr(10 mmol) and water (30 mL) was prepared and heated at 100 C for8 h. After cooling, solid NaOH (25 mmol) was added. The solution wasfiltered and then mixed with HCl until pH= 1. Crude product was collectedand purified on a silica gel column to give L1B as white solid. 1HNMR (CDCl3): delta 8.21 (1H, t), 8.25 (1H, t), 8.33 (1H, d, J = 6.0), 8.85(1H, d, J=3.6).

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  • 2
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  • [ 171018-18-1 ]
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  • [ 33893-89-9 ]
  • [ 75-65-0 ]
  • [ 171018-18-1 ]
  • 1-t-Butyl-5-(2-pyridyl)tetrazole [ No CAS ]
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  • 2-(2-benzyloxymethyl-2<i>H</i>-tetrazol-5-yl)-pyridine [ No CAS ]
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  • [ 7647-01-0 ]
  • [ 1005-02-3 ]
  • NaNO2 [ No CAS ]
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  • 14
  • [ 1121-60-4 ]
  • [ 33893-89-9 ]
YieldReaction ConditionsOperation in experiment
88% With sodium azide; hydroxylamine hydrochloride In N,N-dimethyl-formamide at 140℃; for 8h; 2.5 General procedure for the synthesis of 5-substituted 1H-tetrazole derivatives exploitaion of ruthenium(II) catalyst 3 (0017) General procedure: A solution of substituted aldehyde (1mmol), NH2OH.HCl (1mmol), NaN3 (1.5mmol) and Ru(II) catalyst 3 (0.5mol%) in 3mL of DMF was heated at 140°C for 8h. The progress of the reaction was monitored by TLC and, upon completion, the solvent was evaporated and the residue was dissolved in water (5mL). The solution was acidified with HCl (37%) and the product was purified by column chromatography using 100-200 mesh silica gel and a hexane/ethyl acetate (7:3) mixture as eluent.
82% Stage #1: pyridine-2-carbaldehyde With ammonia; iodine In tetrahydrofuran; water at 20℃; for 1h; Stage #2: With sodium azide; zinc dibromide In tetrahydrofuran; water for 12h; Heating; Further stages.;
  • 15
  • [ 33893-89-9 ]
  • [ 38430-03-4 ]
  • 5-(2-pyridyl)-2-phenyl-3H-1,3,4-benzotriazepine [ No CAS ]
  • 16
  • [ 33893-89-9 ]
  • 2-(1H-tetrazol-5-yl)pyridine 1-oxide [ No CAS ]
YieldReaction ConditionsOperation in experiment
70% With 3-chloro-benzenecarboperoxoic acid; In ethanol; at 20℃; 1 mmol of pyridine tetrazole (Hpytz) and 2.5 mmol of m-chloroperoxybenzoic acid (Mcpba) were added in 180 mL of ethanol and stirred at room temperature. Haziness occured after 30 min which indicated the formation of white precipitate of crystals of pyridine tetrazole-N-oxide
  • 17
  • [ 109-04-6 ]
  • <1,3>dioxolan-2-ylidene-malonodinitrile [ No CAS ]
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  • [ 5346-38-3 ]
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  • [ 33893-89-9 ]
  • iron(II) chloride [ No CAS ]
  • FeCl(1+)*C5NH4CN4(1-)*2H2O = FeClC5NH4CN4*2H2O [ No CAS ]
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  • ammonium hexafluorophosphate [ No CAS ]
  • [ 33893-89-9 ]
  • [ 26042-63-7 ]
  • cis-bis-(2,2′-bipyridine) dichlororuthenium(II) dihydrate [ No CAS ]
  • [ 171018-04-5 ]
  • 21
  • [ 33893-89-9 ]
  • [ 7732-18-5 ]
  • [ 10099-58-8 ]
  • [ 121-44-8 ]
  • [tris(1H-5-(2-pyridyl)tetrazolate)hydroxylanthanum(III)] triethylammonium hydrate [ No CAS ]
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  • [ 7732-18-5 ]
  • [ 10099-58-8 ]
  • [ 910780-37-9 ]
  • 23
  • [ 33893-89-9 ]
  • [IrCl(2-(3',5'-difluorophenyl)-4-methoxypyridinato-N,C2')]2 [ No CAS ]
  • [ 75-09-2 ]
  • (bis[2-(3',5'-difluorophenyl)-4-methoxypyridinato-N,C2']iridium(III) [5-(2'-pyridyl)tetrazolate])*0.5CH2Cl2 [ No CAS ]
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  • [ 33893-89-9 ]
  • [IrCl(2-(3',4'-difluorophenyl)-4-methoxypyridinato-N,C2')]2 [ No CAS ]
  • [ 75-09-2 ]
  • (bis[2-(3',4'-difluorophenyl)-4-methoxypyridinato-N,C2']iridium(III) [5-(2'-pyridyl)tetrazolate])*0.5CH2Cl2 [ No CAS ]
  • 25
  • [ 33893-89-9 ]
  • [IrCl(2-(2',3'-difluorophenyl)-4-methoxypyridinato-N,C2')]2 [ No CAS ]
  • [ 75-09-2 ]
  • (bis[2-(2',4'-difluorophenyl)-4-methoxypyridinato-N,C2']iridium(III) [5-(2'-pyridyl)tetrazolate])*CH2Cl2 [ No CAS ]
  • 26
  • [ 33893-89-9 ]
  • [IrCl(2-(2',3'-difluorophenyl)-4-methoxypyridinato-N,C2')]2 [ No CAS ]
  • [ 75-09-2 ]
  • (bis[2-(2',3'-difluorophenyl)-4-methoxypyridinato-N,C2']iridium(III) [5-(2'-pyridyl)tetrazolate])*0.5CH2Cl2 [ No CAS ]
  • 27
  • [ 33893-89-9 ]
  • [IrCl(2-(2',5'-difluorophenyl)-4-methoxypyridinato-N,C2')]2 [ No CAS ]
  • [ 75-09-2 ]
  • (bis[2-(2',5'-difluorophenyl)-4-methoxypyridinato-N,C2']iridium(III) [5-(2'-pyridyl)tetrazolate])*0.5CH2Cl2 [ No CAS ]
  • 28
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  • [ 3385-78-2 ]
  • [ 1005216-98-7 ]
  • 29
  • [ 33893-89-9 ]
  • chloro(1-phenylpyrazole)iridium(III) dimer [ No CAS ]
  • [ 947408-31-3 ]
  • 30
  • [ 33893-89-9 ]
  • [ 631921-37-4 ]
  • bis(3-methyl-1-phenylpyrazolato-N,C(2'))iridium(III) [5-(2'-pyridyl)tetrazolate] [ No CAS ]
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  • gadolinium(III) chloride hydrate [ No CAS ]
  • [ 7732-18-5 ]
  • [ 960590-86-7 ]
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  • holmium(III) chloride hydrate [ No CAS ]
  • [ 7732-18-5 ]
  • [ 960590-89-0 ]
  • 33
  • [ 33893-89-9 ]
  • ytterbium trichloride hydrate [ No CAS ]
  • [ 7732-18-5 ]
  • [Yb2(5-(2-pyridyl)tetrazolate)4(μ-OH)2(H2O)4]*4H2O [ No CAS ]
  • 34
  • [ 33893-89-9 ]
  • lanthanum(III) chloride hydrated [ No CAS ]
  • [ 7732-18-5 ]
  • [ 960590-84-5 ]
  • 35
  • [ 67-56-1 ]
  • [ 33893-89-9 ]
  • [ 7732-18-5 ]
  • [ 10361-92-9 ]
  • [Y2(5-(2-pyridyl)tetrazolate)4(μ-OH)2(H2O)2(CH3OH)2]*4H2O [ No CAS ]
  • 36
  • [ 33893-89-9 ]
  • bis((2-pyridinyl-κN)phenyl-κ2C)iridium(III) chloride dimer [ No CAS ]
  • Ir(phenylpyridine)(2-(1H-tetrazol-5-yl)pyridine) [ No CAS ]
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  • [ 25433-30-1 ]
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  • [ 103-72-0 ]
  • [ 63279-76-5 ]
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  • [ 103-71-9 ]
  • [ 60838-23-5 ]
  • 41
  • [ 33893-89-9 ]
  • C9H7ClN4O [ No CAS ]
  • 2-[5-(5-methyl-1-phenyl-1H-1,2,3-triazol-4-yl)-1,3,4-oxadiazol-2-yl]pyridine [ No CAS ]
  • 42
  • [ 33893-89-9 ]
  • C9H6ClFN4O [ No CAS ]
  • 2-{5-[1-(4-fluorophenyl)-5-methyl-1H-1,2,3-triazol-4-yl]-1,3,4-oxadiazol-2-yl}pyridine [ No CAS ]
  • 43
  • [ 33893-89-9 ]
  • C9H6Cl2N4O [ No CAS ]
  • 2-{5-[1-(2-chlorophenyl)-5-methyl-1H-1,2,3-triazol-4-yl]-1,3,4-oxadiazol-2-yl}pyridine [ No CAS ]
  • 44
  • [ 33893-89-9 ]
  • C9H6Cl2N4O [ No CAS ]
  • 2-{5-[1-(3-chlorophenyl)-5-methyl-1H-1,2,3-triazol-4-yl]-1,3,4-oxadiazol-2-yl}pyridine [ No CAS ]
  • 45
  • [ 33893-89-9 ]
  • C12H13ClN4O [ No CAS ]
  • 2-{5-[1-(4-isopropylphenyl)-5-methyl-1H-1,2,3-triazol-4-yl]-1,3,4-oxadiazol-2-yl}pyridine [ No CAS ]
  • 46
  • [ 33893-89-9 ]
  • C10H9ClN4O2 [ No CAS ]
  • 2-{5-[1-(2-methoxylphenyl)-5-methyl-1H-1,2,3-triazol-4-yl]-1,3,4-oxadiazol-2-yl}pyridine [ No CAS ]
  • 47
  • chromium(III) nitrate [ No CAS ]
  • [ 33893-89-9 ]
  • [ 7732-18-5 ]
  • Cr2(2-(tetrazol-5-yl)pyridine)4(OH)2 [ No CAS ]
  • 48
  • [ 33893-89-9 ]
  • [ 7732-18-5 ]
  • [ 10025-73-7 ]
  • Cr(2-(tetrazol-5-yl)pyridine)2(H2O)Cl [ No CAS ]
  • 49
  • [ 33893-89-9 ]
  • 1-cyclopenta-2,4-dienylketenimine [ No CAS ]
  • [ 1345346-07-7 ]
YieldReaction ConditionsOperation in experiment
for 4h;UV-irradiation; Ar matrix; General procedure: The crystalline sample of the studied compounds was placed in a small electric oven assembled inside the cryostat. The temperature of the oven was controlled by the DC regulated power supply (NDN Instruments) that allowed for the precise regulation of the current. Matrices were prepared by co-deposition of P2T, P3T or PT vapours coming out of the oven with large excess of argon onto the cold CsI window. The low temperature was maintained by means of a closed cycle helium refrigerator (ARS-2HW). FTIR spectra were recorded between 4000-400 cm-1 in a transmission mode by means of a Bruker 66 FTIR spectrometer with a resolution of 0.5 cm-1 and using a liquid N2 cooled MCT detector.CommentAfter the infrared spectra of the initially deposited matrices were recorded the samples were irradiated with a 450 W output power of a Xe lamp (Optel ZXE-450) for up to 240 min. The lamp was fitted with a 5 cm water filter and a series of long-pass optical filters (Schott WG: 435, 394, 345, 320, 305, 295 and 280 nm).
  • 50
  • [ 629-03-8 ]
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  • [ 1354945-93-9 ]
  • [ 1354945-92-8 ]
  • 51
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  • [ 2094-72-6 ]
  • [ 828-51-3 ]
  • [ 1415251-74-9 ]
YieldReaction ConditionsOperation in experiment
50% With pyridine;Inert atmosphere; Reflux; The reaction was performed with 5-(2'-pyridyl)-1H-tetrazole (500 mg, 3.40 mmol) and 1-adamantanecarboxylic acid chloride (675 mg, 3.40 mmol, Acros) in pyridine (3.5 mL). The reaction mixture was extracted with ether/H2O. The organic layer was washed with water (to remove pyridine) and evaporated. Purification by column chromatography was performed on silica (10 g). Elution with CH2Cl2 removed the impurities. Elution with 0.5% of CH3OH in CH2Cl2 recovered the product. It was re-dissolved in ether, and hexane (20 mL) was added. The ether was rotor-evaporated to leave a suspension of the product in hexane. The suspension was cooled to -15 C overnight and filtered. The product was washed with cold hexane. The product purified in this way contained 10% of 1-adamantanecarboxylic acid (detected by 1H and 13C NMR). To remove the acid, the product was sonicated in saturated aqueous solution of Na2CO3 for 10 min and extracted with ether. The organic layer was washed with saturated aqueous solution of Na2CO3 and water. It was evaporated, and the extraction with Na2CO3 (aq. sat.) and ether was repeated one more time. White solid: 477 mg (1.70 mmol, 50%). Anal. Calc. for C17H19N3O (MW 281.35): C, 72.57; H, 6.81; N, 14.94. Found: C, 72.54; H, 6.87; N, 14.74%. 1H NMR (400 MHz, [D6]dmso): delta = 8.79-8.74 (m, 1H), 8.19-8.13 (m, 1H), 8.03 (td, J = 8.0, 1.6 Hz, 1H), 7.62 (ddd, J = 7.6, 4.8, 1.2 Hz, 1H), 2.10-2.04 (m, br, 9H), 1.77 (br, 6H) ppm. 13C NMR (100 MHz, CD2Cl2): delta = 173.68, 163.90, 150.34, 144.25, 137.28, 125.72, 123.00, 40.12, 36.44, 34.71, 28.13 ppm. GC-EI+ MS: m/z 281 (M+, 100%).
  • 52
  • [ 33893-89-9 ]
  • [ 938-18-1 ]
  • C38H31IrN5O(1+)*F6P(1-) [ No CAS ]
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  • [ 938-18-1 ]
  • [ 1415251-75-0 ]
YieldReaction ConditionsOperation in experiment
84% With pyridine;Inert atmosphere; Reflux; The reaction was performed with 5-(2'-pyridyl)-1H-tetrazole (730 mg, 4.96 mmol) and 2,4,6-trimethylbenzoyl chloride (906 mg, 0.83 mL, 4.96 mmol, AlfaAesar) in pyridine (3.5 mL). The reaction mixture was diluted with water (50 mL) to give suspension. It was stirred for 10 min. The precipitate of the crude product was filtered, washed with water, and extracted with ether/H2O. The organic layer was washed with water and evaporated. Purification by column chromatography was performed on silica (15 g). Elution with CH2Cl2 removed pale yellow impurity. Elution with 0.5% CH3OH in CH2Cl2 recovered the product. White solid: 1.10 g (4.15 mmol, 84%). Anal. Calc. for C16H15N3O (MW 265.31): C, 72.43; H, 5.70; N, 15.84. Found: C, 72.24; H, 5.74; N, 15.53%. 1H NMR (400 MHz, [D6]dmso): delta = 8.79 (dd, J = 4.8, 0.8 Hz, 1H), 8.24 (dd, J = 8.0, 0.8 Hz, 1H), 8.12-8.04 (m, 1H), 7.69-7.62 (m, 1H), 7.09 (s, 2H), 2.33 (s, 3H), 2.25 (s, 6H) ppm. 13C NMR (100 MHz, CD2Cl2): delta = 164.96, 164.51, 150.52, 144.09, 141.48, 138.98, 137.39, 129.06, 125.98, 123.13, 121.19, 21.26, 20.44 ppm. GC-EI+ MS: m/z 265 (M+, 100%).
  • 54
  • [ 33893-89-9 ]
  • [ 83-01-2 ]
  • [ 1415251-76-1 ]
YieldReaction ConditionsOperation in experiment
90% With pyridine;Inert atmosphere; Reflux; The reaction was performed with 5-(2'-pyridyl)-1H-tetrazole (437 mg, 2.97 mmol) and diphenylcarbamoyl chloride (693 mg, 2.99 mmol, AlfaAesar) in pyridine (3 mL). The reaction mixture on cooling to RT gave suspension. It was diluted with solution of Na2CO3 (sat. aq.) and extracted with CH2Cl2. The organic layer was washed with water and evaporated. Purification by column chromatography was performed on silica (15 g). Elution with CH2Cl2 removed yellow impurity. Elution with 0.5-1.0% CH3OH in CH2Cl2 recovered the product. It was re-dissolved in CH2Cl2, and ethanol (20 mL) was added. Dichloromethane was rotor-evaporated to leave a suspension of the product in ethanol. It was cooled to room temperature, filtered, and washed with hexane. White solid: 839 mg (2.67 mmol, 90%). Anal. Calc. for C19H14N4O (MW 314.34): C, 72.60; H, 4.49; N, 17.82. Found: C, 72.66; H, 4.54; N, 17.54%. 1H NMR (400 MHz, [D6]dmso): delta = 8.66-8.62 (m, 1H), 8.03-7.94 (m, 2H), 7.55-7.51 (m, 1H), 7.50-7.44 (m, 4H), 7.43-7.38 (m, 4H), 7.35-7.29 (m, 2H) ppm. 13C NMR (100 MHz, CD2Cl2): delta = 163.34, 159.67, 150.20, 144.03, 142.58, 137.16, 129.79, 126.69, 125.64, 125.24, 122.19 ppm. ESI+ TOF MS: m/z 314 (M+, 70%).
  • 55
  • dodecatungstosilic acid [ No CAS ]
  • [ 33893-89-9 ]
  • copper(II) choride dihydrate [ No CAS ]
  • [ 7732-18-5 ]
  • {Cu5(5-(2-pyridyl)tetrazole)6(H2O)4(SiW12O40)}·4H2O [ No CAS ]
  • 56
  • phosphomolybdic acid [ No CAS ]
  • [ 33893-89-9 ]
  • copper(II) choride dihydrate [ No CAS ]
  • [ 7732-18-5 ]
  • {Cu9(5-(2-pyridyl)tetrazole)12(H2O)6(PMo12O40)2}*H2O [ No CAS ]
  • 57
  • [ 17084-13-8 ]
  • [ 33893-89-9 ]
  • [ 921934-01-2 ]
  • C28H25N9Pt(1+)*F6P(1-) [ No CAS ]
  • 58
  • [ 33893-89-9 ]
  • [ 14099-01-5 ]
  • [ 1440544-05-7 ]
  • 59
  • [ 33893-89-9 ]
  • [ 14220-21-4 ]
  • [ 1440544-05-7 ]
  • 60
  • [ 33893-89-9 ]
  • tetrakis(acetonitrile)copper(I)tetrafluoroborate [ No CAS ]
  • [ 161265-03-8 ]
  • [Cu(9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene)(2-(tetrazol-5-yl)pyridine)]BF4 [ No CAS ]
  • 61
  • [ 33893-89-9 ]
  • tetrakis(acetonitrile)copper(I)tetrafluoroborate [ No CAS ]
  • [ 603-35-0 ]
  • [Cu(triphenylphosphine)2(2-(tetrazol-5-yl)pyridine)]BF4 [ No CAS ]
  • 62
  • [ 33893-89-9 ]
  • tetrakis(acetonitrile)copper(I)tetrafluoroborate [ No CAS ]
  • [ 166330-10-5 ]
  • [Cu(bis[2-(diphenylphosphino)phenyl]ether)(2-(tetrazol-5-yl)pyridine)][Cu(bis[2-(diphenylphosphino)phenyl]ether)(5-(2-pyridyl)-tetrazolate)]BF4 [ No CAS ]
  • 63
  • [ 33893-89-9 ]
  • tetrakis(acetonitrile)copper(I)tetrafluoroborate [ No CAS ]
  • [ 1215039-29-4 ]
  • [Cu(bis[2-(diphenylphosphino)-p-tolyl] ether)(2-(tetrazol-5-yl)pyridine)]BF4 [ No CAS ]
  • 64
  • [ 33893-89-9 ]
  • [ 64443-05-6 ]
  • [ 166330-10-5 ]
  • C42H33CuN5OP2(1+)*C42H32CuN5OP2*F6P(1-) [ No CAS ]
  • 65
  • [ 33893-89-9 ]
  • [ 161265-03-8 ]
  • [ 1445903-73-0 ]
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  • [ 33893-89-9 ]
  • [ 603-35-0 ]
  • [ 1416587-30-8 ]
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  • [ 1443681-88-6 ]
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  • [ 1443681-89-7 ]
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  • [ 1375071-03-6 ]
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  • [ 1443681-90-0 ]
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  • [ 33893-89-9 ]
  • [ 1443681-91-1 ]
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  • [ 1443681-95-5 ]
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  • [ 1443681-96-6 ]
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  • [ 1443682-02-7 ]
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  • [ 1443681-61-5 ]
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  • [ 1443681-66-0 ]
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