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[ CAS No. 838-34-6 ] {[proInfo.proName]}

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Chemical Structure| 838-34-6
Chemical Structure| 838-34-6
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Product Details of [ 838-34-6 ]

CAS No. :838-34-6 MDL No. :
Formula : C14H11NO2 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 225.24 Pubchem ID :-
Synonyms :

Safety of [ 838-34-6 ]

Signal Word: Class:
Precautionary Statements: UN#:
Hazard Statements: Packing Group:

Application In Synthesis of [ 838-34-6 ]

* 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 [ 838-34-6 ]

[ 838-34-6 ] Synthesis Path-Downstream   1~11

  • 1
  • [ 100-09-4 ]
  • [ 95-55-6 ]
  • [ 838-34-6 ]
YieldReaction ConditionsOperation in experiment
97% With poly(ethylene glycol)-bound sulphonic acid In 1,4-dioxane; chloroform at 60 - 65℃; 2.3.2. General Procedure for Synthesis of Substituted Benzoxazole Derivatives starting from Substituted 2-Amino Phenols and Substituted Benzoic Acids (Scheme 2) General procedure: A solution of substituted 2-amino phenols (10 mmol) was prepared in mixture of dioxane:chloroform (1:1) arranged in a three neck flask, to it a solution of substituted benzoic acid (10 mmol) in chloroform was added drop wise over a period of 1 hour with constant stirring. To this mixture PEG-SO3H (2.1 mmol) was added and the reaction was carried out for 5 to 6 hours at 60-65 °C, progress of the reaction was monitored by TLC. After completion of reaction as determined by TLC, the reaction mixture was cooled to room temperature and the resulting solid was washed with strong ammonia solution and filtered to remove catalyst, then dried under vacuum (Scheme 2). The resulting products were recrystallized from rectified spirits to obtain substituted 2-aminobenzoxazole (Table 3).
88% With trimethylsilylphosphate In 1,2-dichloro-benzene for 2h; Heating;
84% With samarium(III) trifluoromethanesulfonate In ethanol; water at 80℃; for 4h; General procedure for the synthesis of benzoxazoles/benzothiazole General procedure: To a mixture of o-aminophenol/o-aminothiophenol (1 mmol) and carboxylic acids (1 mmol) in ethanol:water (2:2 mL) under open atmosphere, 10 mol% of samarium triflate catalyst were added. The resulting mixture was stirred at 80 °C. After completion of the reaction, as monitored by TLC, the reaction mixture was diluted with 1:1 mixture of water/ethyl acetate (10 mL) and catalyst recovered by simplefiltration. The reaction mixture was extracted with diethyl ether (2 x 10 mL) and dried with anhydrous sodium sulfate. Finally, crude product was recrystallized from ethyl acetate or methanol. All the pure products were confirmed by their 1 HNMR, 13C NMR, IR, and mass spectroscopy data.
59% In xylene for 27h; Heating;
37% With tin(ll) chloride In 1,4-dioxane at 180℃; for 30h;
With PPA at 100℃; for 2.5h;
94 %Chromat. With H5[PMo10V2O40] In tetrahydrofuran for 6h; Reflux;

  • 2
  • [ 273-53-0 ]
  • [ 696-62-8 ]
  • [ 838-34-6 ]
YieldReaction ConditionsOperation in experiment
93% With bis(triphenylphosphine)copper(I) cyanide; caesium carbonate; triphenylphosphine for 24h; Reflux;
89% With [Pd(1,10-phenanthroline)2](PF6)2; caesium carbonate In dimethyl amine at 150℃; for 20h; Inert atmosphere;
89% With {(H3O)[Cu2(CN)(TTB)0.5]·1.5H2O}n; potassium carbonate In N,N-dimethyl-formamide at 140℃; for 10h;
84% With potassium carbonate In dimethyl sulfoxide at 100℃; for 4h; Green chemistry; 2. General process for thesynthesis of 2-substituted benzoxazole (Scheme 1). General procedure: Benzoxazole (1.0 mmol), iodobenzene (1 mmol), 2mmol K2CO3 and 5 mol% of nano CeO2-Fe3O4 catalyst were added in DMSO (1 mL) and the reaction was carried at 100 C for 4h. The progress of the reaction was monitored by Gas Chromatography (GC). After completion of reaction, the reaction mixture was cooled to room temperature and it was extracted with ethyl acetate dried over Na2SO4. The solvent was evaporated under reduced pressure to obtain product. The catalyst was easily recovered by magnetic separation followed by washing with ethanol and drying and preserved for next runs. The pure products were obtained by column chromatography using hexane: ethyl acetate as the eluent. The preserved catalyst reused in a subsequent run for recyclability study. The conversion of reactant was determined by Gas chromatography (GC).
81% With potassium carbonate; copper(II) oxide In diethylene glycol dimethyl ether for 3h; Inert atmosphere; Reflux;
80% With lithium tert-butoxide In N,N-dimethyl-formamide at 140℃; for 0.166667h;
73% With [(1,5-cyclooctadiene)2RhCl]2; triethylamine; tricyclohexylphosphine In tetrahydrofuran at 150℃; for 6h;
71% With copper(l) iodide; sodium carbonate; triphenylphosphine In N,N-dimethyl-formamide at 160℃; for 2h;
61% With copper(l) iodide; 2-(N-butyl-benzimidazol-2-yl)-6-(diphenylphosphinoxy)phenylchloropalladium(II); caesium carbonate In N,N-dimethyl-formamide at 120℃; for 18h; Inert atmosphere; 4.4.1. General procedure for the catalytic C-H arylation of azoles with aryl iodides General procedure: To a stirred solution of Cs2CO3 (0.75 mmol) and CuI (1.25 mol%)in DMF (1.0 mL) was added aryl iodide (0.75 mmol), azole (0.5mmol) and 4a (0.25 mol%) under argon atmosphere at room temperature. Then the mixture was stirred at 120 °C for 18 h. After cooling, filtration, and evaporation, the residue was purified by preparative TLC on silica gel plates eluting with petroleum ether/EtOAc to afford the corresponding products.
52% With [2,2]bipyridinyl; copper(I) thiophene-2-carboxylate; lithium tert-butoxide In N,N-dimethyl-formamide at 20℃; for 16h; Irradiation; Inert atmosphere;
With potassium phosphate; Cu2(4,4’-biphenyldicarboxylate)2(4,4’-bipyridine) In Hexadecane; N,N-dimethyl-formamide at 120℃; for 3h; Green chemistry; General procedure: In a typical experiment, a pre-determined amount of Cu2(BPDC)2(BPY) was added to theflask containing a solution of iodobenzene (0.112 mL, 1 mmol),benzoxazole (0.238 g, 2 mmol), K3PO4(0.532 g, 2 mmol) and n-hexadecane (0.1 mL) as internal standard in DMF (4 mL). Thecatalyst concentration was calculated based on the molar ratio ofcopper/iodobenzene. The reaction mixture was stirred at 100Cunder an argon atmosphere for 180 min. The reaction conver-sion was monitored by withdrawing aliquots from the reactionmixture at different time intervals, quenching with an aqueousNaOH solution (5%, 1 mL), drying over anhydrous Na2SO4, analyz-ing by GC with reference to n-hexadecane, and further confirmingproduct identity by GC-MS. To investigate the recyclability ofCu2(BPDC)2(BPY), the catalyst was filtered from the reaction mix-ture after the experiment, washed with copious amounts of DMF,dried under air at room temperature for 1 h, and reused if neces-sary. For the leaching test, a catalytic reaction was stopped after30 min, analyzed by GC, and filtered to remove the solid catalyst.The reaction solution was then stirred for a further 150 min. Reac-tion progress, if any, was monitored by GC as previously described.

Reference: [1]Kim, Donghae; Yoo, Kwangho; Kim, Se Eun; Cho, Hee Jin; Lee, Junseong; Kim, Youngjo; Kim, Min [Journal of Organic Chemistry, 2015, vol. 80, # 7, p. 3670 - 3676]
[2]Shibahara, Fumitoshi; Yamaguchi, Eiji; Murai, Toshiaki [Chemical Communications, 2010, vol. 46, # 14, p. 2471 - 2473]
[3]Huang, Chao; Wu, Jie; Song, Chuanjun; Ding, Ran; Qiao, Yan; Hou, Hongwei; Chang, Junbiao; Fan, Yaoting [Chemical Communications, 2015, vol. 51, # 51, p. 10353 - 10356]
[4]Shelkar, Radheshyam S.; Balsane, Kishor E.; Nagarkar, Jayashree M. [Tetrahedron Letters, 2015, vol. 56, # 5, p. 693 - 699]
[5]Location in patent: experimental part Zhang, Wu; Zeng, Qinglong; Zhang, Xinming; Tian, Yujie; Yue, Yun; Guo, Yujun; Wang, Zhenghua [Journal of Organic Chemistry, 2011, vol. 76, # 11, p. 4741 - 4745]
[6]Do, Hien-Quang; Daugulis, Olafs [Journal of the American Chemical Society, 2007, vol. 129, # 41, p. 12404 - 12405]
[7]Lewis, Jared C.; Wiedemann, Sean H.; Bergman, Robert G.; Ellman, Jonathan A. [Organic Letters, 2004, vol. 6, # 1, p. 35 - 38]
[8]Yoshizumi, Tomoki; Tsurugi, Hayato; Satoh, Tetsuya; Miura, Masahiro [Tetrahedron Letters, 2008, vol. 49, # 10, p. 1598 - 1600]
[9]Wang, Cong; Li, Yang; Lu, Beibei; Hao, Xin-Qi; Gong, Jun-Fang; Song, Mao-Ping [Polyhedron, 2018, vol. 143, p. 184 - 192]
[10]Ma, Xiaodong; Zhang, Guozhu [Chinese Journal of Chemistry, 2020, vol. 38, # 11, p. 1299 - 1303]
[11]Le, Hanh T.N.; Nguyen, Tung T.; Vu, Phuong H.L.; Truong, Thanh; Phan, Nam T.S. [Journal of Molecular Catalysis A: Chemical, 2014, vol. 391, # 1, p. 74 - 82]
  • 3
  • [ 1141-35-1 ]
  • [ 838-34-6 ]
YieldReaction ConditionsOperation in experiment
87% With sodium methylate; dimethyl sulfoxide In water 5 Synthesis of 2-(p-methoxyphenyl)benzoxazole EXAMPLE 5 Synthesis of 2-(p-methoxyphenyl)benzoxazole A mixture of 1.15 g (5 mmoles) of 2-(p-chloro-phenyl)benzoxazole, 2.5 g of sodium methoxide and 10 ml of dimethyl sulfoxide is heated at 80° C.-90° C. under nitrogen atmosphere for one hour. The mixture is cooled and diluted with 100 ml of water. The title compound (1 g, 87 percent yield) precipitates and is recovered. It has a melting point of 99.5° C.-101.5° C.
  • 6
  • [ 2393-23-9 ]
  • [ 95-55-6 ]
  • [ 838-34-6 ]
YieldReaction ConditionsOperation in experiment
92% With 1-hydroxytetraphenylcyclopentadienyl(tetraphenyl-2,4-cyclopentadien-1-one)-μ-hydrotetracarbonyldiruthenium(II); 2,6-dimethoxy-p-quinone; bis(salicylideniminato-3-propyl)methylamino-cobalt(II) In chlorobenzene at 120℃; for 24h;
87% With iron(III) sulfate; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical In neat (no solvent) at 110℃; for 24h; Green chemistry; Typical procedure for aerobic oxidative synthesisof benzimidazoles, benzoxazoles, or benzothiazoles General procedure: A mixture of 6 mmol of the alcohol or the amine and5 mmol o-phenylenediamine, o-aminophenol or o-aminothiophenol,10 mol % Fe2(SO4)3, 10 mol % TEMPO wasprepared in a 10 ml three-necked flask, and then stirred inopen air at 110 °C for several hours, The reaction progresswas monitored by TLC. When the final reaction mixturecooled to room temperature, the crude products was directlypurified by column chromatography on silica gel using hexane/ethyl acetate (7:3) as eluent to afford the pure product.
85% With 2,2,6,6-tetramethyl-piperidine-N-oxyl; ferric nitrate In neat (no solvent) at 110℃; for 28h; Green chemistry;
82% With iron(III) chloride; 3-methyl-4-oxa-5-azahomoadamantane; oxygen In water at 100℃; for 18h; Typical procedure for oxidative synthesis of benzimidazoles, benzoxazolesor benzothiazoles General procedure: A mixture of 1.2 mmol o-phenylenediamine, 2-aminophenol or 2-aminothiophenol and 1 mmol primary amine, 10 mol % FeCl3, 1 mol % 3-methyl-4-oxa-5-azahomoadamantane, 5 ml H2O were mixed in a 10-ml three-necked flask, then O2 was bubbled into the flask at flow rate of 20 ml/min. The reaction mixture was stirred at 100 C for several hours, and reaction progress was monitored by TLC. The final reaction mixture was cooled to room temperature and extracted with ethyl acetate. The organic layer was washed with brine, dried over MgSO4, and concentrated under reduced pressure. The residue was directly purified by column chromatography on silica gel using hexane/ethyl acetate (7:3) as eluent to afford the pure product.
78% With disodium hydrogenphosphate; 4-tert-butyl-5-methoxy-1,2-benzoquinone; oxygen In chlorobenzene at 100℃; for 36h; Schlenk technique;
70% With 2,6-dimethoxy-p-quinone In 1,3,5-trimethyl-benzene at 150℃; for 24h; Inert atmosphere; Radley's carousel;

  • 7
  • [ 13673-62-6 ]
  • 4-MeOC6H4ZnI*LiCl [ No CAS ]
  • [ 838-34-6 ]
  • 8
  • [ 273-53-0 ]
  • [ 19013-30-0 ]
  • [ 838-34-6 ]
YieldReaction ConditionsOperation in experiment
97% With palladium diacetate; caesium carbonate; cesium pivalate; 1,2-bis-(dicyclohexylphosphino)ethane In toluene at 120℃;
46% Stage #1: benz<b>oxazole; p-methoxyphenyl mesylate With 2-[2-(dicyclohexylphosphino)-phenyl]-1-methyl-1H-indole; palladium diacetate; potassium carbonate; triethylamine Inert atmosphere; Stage #2: In N,N-dimethyl-formamide; <i>tert</i>-butyl alcohol at 110℃; for 24h; Inert atmosphere;
  • 9
  • [ 273-53-0 ]
  • [ 5720-07-0 ]
  • [ 838-34-6 ]
YieldReaction ConditionsOperation in experiment
97% With C46H62Cl3N3Pd; sodium t-butanolate In ethanol; water at 80℃; for 3.33333h; Green chemistry;
88% With potassium phosphate; 1,10-Phenanthroline; copper diacetate; palladium diacetate In dimethyl sulfoxide at 100℃; for 24h;
87% With iron(III) chloride; 1,10-Phenanthroline; 1,2-dichloro-2-methylpropane; caesium carbonate In N,N-dimethyl-formamide at 100℃; for 16h; Sealed tube; Inert atmosphere; 4. General experimental procedure for the synthesis of products (3a-v) using Fe(III)-catalyzed reactions (Method A) General procedure: A 10 mL pressure tube was charged with a mixture of oxazoles or thiazoles 1a-f (1.0 mmol),boronic acids 2a-o (1.0 mmol), FeCl3 (0.05 mmol), 1,10-Phenanthroline (0.1 mmol), DCIB(1.3 mmol), Cs2CO3 (1.5 mmol) and DMF (2 mL). The pressure tube was then sealed andheated at 100 °C for 16 h. After completion of the reaction (progress was monitored by TLC;SiO2, Hexane/EtOAc = 9:1), the mixture was diluted with hot ethyl acetate (20 mL) andwater (40 mL) and extracted with ethyl acetate (3 × 10 mL). The combined organic layer waswashed with brine (2 × 10 mL) and dried over anhydrous Na2SO4. Solvent was removedunder reduced pressure and the remaining residue was purified by column chromatography over silica gel using hexane / ethyl acetate = 9:1 as an eluent to obtain the desired products3a-v in high yields.
86% With potassium carbonate In 5,5-dimethyl-1,3-cyclohexadiene at 100℃; for 9.5h; Green chemistry; 2.5 General Method for C-H Arylation of Benzoxazole with Aryl Boronic Acids General procedure: A mixture of benzoxazole (1mmol), aryl boronic acid(1 mmol), K2CO3(2mmol) and MNPFemBenzNHCNi complex (7) (100mg) in xylene (5mL) was stirred at100°C. The progress of reaction was monitored by TLC.After completion of reaction, 7 was separated by usingexternal magnet. Evaporation of solvent in vaccuo followedby column chromatography over silica gel using petroleumether/ethyl acetate aforded pure products. The productswere identified by FT-IR, 1H NMR, 13C NMR and mass
With [2,2]bipyridinyl; potassium phosphate; [(nickel(II))2(1,4 dicarboxybenzene)2(1,4-diaza-bicyclo[2.2.2]octane)] In N,N-dimethyl acetamide at 100℃; for 3h;

  • 10
  • [ 273-53-0 ]
  • [ 1950-68-1 ]
  • [ 838-34-6 ]
  • 11
  • [ 273-53-0 ]
  • [ 623-12-1 ]
  • [ 838-34-6 ]
YieldReaction ConditionsOperation in experiment
85% With copper(l) iodide; potassium phosphate tribasic heptahydrate; palladium diacetate; nixantphos In N,N-dimethyl-formamide at 120℃; for 24h; Inert atmosphere; 2. General procedure for direct 2-arylation of benzoxazoles with aryl chlorides General procedure: 2 mol% Pd(OAc)2/3 mol% Nixantphos, anhydrous DMF (1.0 ml) were added to an oven-dried 10 ml reaction vial equipped with a stir bar, the mixture was stirred at 45 °C under an argon atmosphere for 1h to be a dark brown solution. 1 mol% CuI/1.1 mol% Nixantphos, anhydrous DMF (1.0 ml) were added to an oven-dried 10 ml reaction vial equipped with a stir bar, the mixture was stirred at 60 °C under an argon atmosphere for 2h to be a colorless transparent solution. The amount of catalyst and solvent should scaled up by the number of reactions. Benzoxazoles (0.25 mmol), aryl chlorides (0.3 mmol) and K3PO4*7H2O (42.3 mg, 0.125 mmol, 0.5 equiv) were added to an oven-dried 10 ml reaction vial equipped with a stir bar. A stock solution of Pd(OAc)2/Nixantphos and CuI/Nixantphos in 1 ml of dry DMF was taken up by syringe and added to the reaction vial. The reaction vial filled with argon was then sealed with a septum. The reaction mixture was stirred for12 h or 24 h at 120 °C, quenched with two drops of H2O, diluted with 3 mL of ethyl acetate, and filtered over a pad of MgSO4 and silica. The pad was rinsed with additional ethyl acetate, and the solution was concentrated in vacuo. The crude material was loaded onto a silica gel column and purified by flash chromatography.
65% With [(SIPr)PdCl(quinoline‐2‐carboxylate)]; sodium t-butanolate In N,N-dimethyl-formamide at 150℃; for 24h;
62% With potassium phosphate; C37H38FeO6P2Pd In butan-1-ol at 125℃; for 18h; Schlenk technique; Inert atmosphere; Sealed tube;
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