- One-pot synthesis of a highly disperse core-shell CuO-alginate nanocomposite and the investigation of its antibacterial and catalytic properties
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In this study, sodium alginate was extracted from Sargassum algae, collected from coastal waters of Bushehr, Persian Gulf, Iran and used as a stabilizing and wrapping agent for CuO nanoparticles. The synthesized nanocomposite was characterized by some spectroscopic and microscopic techniques, such as IR, XRD, Uv-vis, BET, BJH, zeta potential, SEM, TEM, HR-TEM, and XPS. The antibacterial effects of the CuO-alginate nanocomposite against some bacteria, isolated from a burn wound, were evaluated. The results showed that this nanocomposite had better antibacterial effects than its components onPseudomonas aeruginosaATCC 27853,Staphylococcus aureusATCC 12600,Streptococcus pyogenesATCC 19615, andStaphylococcus epidermidisATCC 49461. Among these,Staphylococcus aureusATCC 12600 was the most sensitive one to this nanocomposite, with the lowest minimum inhibitory concentration (2.08 mg mL?1) observed. Moreover, the synthesized nanocomposite showed good catalytic activity in the oxidative coupling of carboxylic acids withN,N-dialkylformamides toward the synthesis of amides.
- Habibi, Hassan,Mansourinejhad, Sanam,Saberi, Dariush,Shadi, Ahmad
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p. 199 - 211
(2021/12/30)
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- Palladium-Catalyzed Aminocarbonylation of Aryl Halides with N,N-Dialkylformamide Acetals
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We developed a protocol for the palladium-catalyzed aminocarbonylation of aryl halides using less-toxic formamide acetals as bench-stable aminocarbonyl sources under neutral conditions. Various aryl (including heteroaryl) halides reacted with N,N-dialkylformamide acetals in the presence of a catalytic amount of tris(dibenzylideneacetone)dipalladium(0)-chloroform adduct and xantphos to give the corresponding aromatic carboxamides at 90–140 °C without any activating agents or bases in up to quantitative chemical yield. This protocol was applied to aryl bromides, aryl iodides, and trifluoromethanesulfonic acid, as well as to relatively less-reactive aryl chlorides. A wide range of functionalities on the aromatic ring of the substrates were tolerated under the aminocarbonylation conditions. The catalytic aminocarbonylation was used to prepare the insect repellent N,N-diethyl-3-methylbenzamide as well as a synthetic intermediate of the dihydrofolate reductase inhibitor triazinate.
- Hirata, Shuichi,Osako, Takao,Uozumi, Yasuhiro
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- Rhoda-Electrocatalyzed Bimetallic C?H Oxygenation by Weak O-Coordination
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Rhodium-electrocatalyzed arene C?H oxygenation by weakly O-coordinating amides and ketones have been established by bimetallic electrocatalysis. Likewise, diverse dihydrooxazinones were selectively accessed by the judicious choice of current, enabling twofold C?H functionalization. Detailed mechanistic studies by experiment, mass spectroscopy and cyclovoltammetric analysis provided support for an unprecedented electrooxidation-induced C?H activation by a bimetallic rhodium catalysis manifold.
- Tan, Xuefeng,Massignan, Leonardo,Hou, Xiaoyan,Frey, Johanna,Oliveira, Jo?o C. A.,Hussain, Masoom Nasiha,Ackermann, Lutz
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supporting information
p. 13264 - 13270
(2021/05/06)
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- POCl3 promoted metal-free synthesis of tertiary amides by coupling of carboxylic acids and N,N-disubstituted formamides
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Herein we report a robust and synthetically useful catalyst-free amination methodology by the coupling of carboxylic acids and N-substituted formamides using POCl3 as a promoter. Versatile amides with a wide array of substituent groups were prepared within only 1 h in good to excellent yields. And even multi-substituted aromatic carboxylic acids could give the desired products with satisfactory results.
- Bi, Xiaojing,Li, Junchen,Shi, Enxue,Li, Yu,Liu, Ying,Wang, Hongmei,Xiao, Junhua
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supporting information
p. 236 - 240
(2019/04/25)
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- Direct Synthesis of Amides from Oxidative Coupling of Benzyl Alcohols and N-substituted Formamides Using a Co–Al Based Heterogeneous Catalyst
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Present work reports the direct synthesis of amides from oxidative coupling of benzyl alcohols with various N-substituted formamides using a cobalt-hydrotalcite (Co-HT) derived catalyst. The Co-HT derived catalysts (Co-HT-2, Co-HT-3 and Co-HT-4 having Co2+/Al3+ molar ratio in the catalyst preparation mixture as 1/1, 2/1 and 3/1 respectively) were prepare following a co-precipitation method and characterized well by powder XRD, XPS, FEG-SEM, EDS, DTG–TGA, FT-IR and N2 physisorption measurements. A range of functional amides were obtained in good yields from oxidative coupling of various substituted benzyl alcohols and a range of N-substituted formamides using Co-HT-3 catalyst and oxidant TBHP. Mechanistic investigation suggests that the amidation reaction is associated with the formation and coupling of radical species. Furthermore, the Co-HT derived catalyst was easily recoverable and recyclable with retained high catalytic activity towards the oxidative coupling of benzyl alcohol with DMF. Graphical Abstract: [Figure not available: see fulltext.].
- Subhedar, Dnyaneshwar D.,Gupta, Shyam Sunder R.,Bhanage, Bhalchandra M.
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p. 3102 - 3111
(2018/08/21)
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- Pd(PPh3)4 catalyzed amide compound synthesis method
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The invention relates to a Pd(PPh3)4 catalyzed amide compound synthesis method. The synthesis method takes carboxylic acid as the substrate, and adopts N-substituted formamide as the amine source to synthesize an amide compound under the catalysis of Pd(PPh3)4. The method is widely applicable to substrates with different functional groups. The amide compound efficiently constructed by the invention is an important skeleton of many organic molecules, drugs, peptides, bioactive molecules and natural products. The synthesis method provided by the invention provides a widely applicable preparation method for synthesis of the compounds.
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Paragraph 0041; 0042; 0043; 0044; 0045
(2017/12/27)
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- Synthesis method of amide aryl compound
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The invention relates to a synthesis method of an amide aryl compounds. According to the method, Ru-(p-cymene) C12 is taken as a catalyst, K2S2O8 is taken as an oxidizing agent, Xantphos is taken as a ligand, one reactant (N, N-dialkyl formamide) is taken
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Paragraph 0030; 0031; 0032; 0033; 0034
(2017/04/19)
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- FeCl3 catalyzed amide compound synthesis method
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The invention relates to an FeCl3 catalyzed amide compound synthesis method. According to the synthesis method, carboxylic acid and N-substituted formamide are employed to synthesize an amide compound under the catalysis of FeCl3. The synthesis method provided by the invention has the characteristics of mild conditions, high reaction efficiency, and wide applicability to substrates of different functional groups. The amide compound efficiently constructed by the invention is an important skeleton of many organic molecules, drugs, proteins and bioactive molecules. The synthesis method provided by the invention provides a widely applicable preparation method for synthesis of the compounds.
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Paragraph 0045; 0046; 0047; 0048; 0049
(2018/03/28)
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- Oxidative amidation of benzaldehydes and benzylamines with: N -substituted formamides over a Co/Al hydrotalcite-derived catalyst
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The present work describes a highly efficient synthetic strategy for amides via oxidative coupling of benzaldehydes or benzylamines with N-substituted formamides using a heterogeneous Co/Al hydrotalcite-derived catalyst in the presence of TBHP. A series of Co/Al hydrotalcite-derived catalysts (Cat-2, Cat-3, and Cat-4 with the Co2+/Al3+ molar ratio in the synthesis mixture as 1/1, 2/1 and 3/1) have been prepared by a simple co-precipitation method and characterized using powder XRD, XPS, FEG-SEM, EDS, FT-IR, DTG-TGA and N2 physical adsorption techniques. Among the as-prepared catalysts, Cat-3 exhibited excellent catalytic activity towards the direct amidation of benzaldehydes as well as benzylamines bearing various substituents into the corresponding amides at 100 °C using TBHP as an oxidant. The mechanistic investigation of the amidation reaction revealed that the reaction follows a radical pathway. Furthermore, the catalyst is easily separable and recyclable without considerable loss in catalytic activity.
- Gupta, Shyam Sunder R.,Nakhate, Akhil V.,Rasal, Kalidas B.,Deshmukh, Gunjan P.,Mannepalli, Lakshmi Kantam
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p. 15268 - 15276
(2017/12/15)
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- Method for synthesizing phosphorus-oxychloride-promoted amide compound
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The invention relates to a method for synthesizing a phosphorus-oxychloride-promoted amide compound. The synthesizing method includes the steps that carboxylic acid serves as one reactant, another reactant (N,N-dialkyl methanamide) serves as a solvent, one equivalent of phosphorus oxychloride is added, and the amide compound is prepared. The reaction substrates are low in price and easy to get, the nature is stable, toxicity is small, the reaction speed is high, conditions are moderate, and the reaction substrates can be widely applied to substrates with different functional groups. The efficiently-constructed amide compound is an important molecular skeleton for many medicines, bioactive molecules and natural products, and the synthesizing method is a widely-applicable preparing method for synthesizing the compound.
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Paragraph 0035; 0036; 0037; 0038; 0039
(2017/01/26)
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- Ru-catalyzed direct amidation of carboxylic acids with N-substituted formamides
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The direct amidation of carboxylic acids with N-substituted formamides has been accomplished via ruthenium catalysis. In the presence of ruthenium catalyst, a versatile range of carboxylic acids and N-substituted formamides undergoes amidation reaction to produce synthetically useful amides in good yields. C[dbnd]O in amide product came from benzoic acid but not N-substituted formamides, and which was confirmed by Isotope experiment.
- Bi, Xiaojing,Li, Junchen,Shi, Enxue,Wang, Hongmei,Gao, Runli,Xiao, Junhua
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p. 8210 - 8214
(2016/11/23)
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- Copper-catalyzed amide bond formation from formamides and carboxylic acids
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A highly efficient copper-catalyzed approach to form amide bonds from formamides and carboxylic acids was developed. This protocol shows broad substrate scopes and high yields in the presence of 1 mol% catalyst and 4.0 equiv. formamides.
- Liu, Hong-Qiang,Liu, Jun,Zhang, Yang-Hui,Shao, Chang-Dong,Yu, Jing-Xun
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- General and efficient oxidative amidation of benzyl alcohols with amines using diacetoxyiodobenzene and TBHP
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A facile oxidative coupling of alcohols and amines to construct amides was developed using DIB as a catalyst and aqueous tert-butyl hydroperoxide as an oxidant. Various secondary and tertiary amides were prepared in good yield utilizing inexpensive and readily available reagents under mild reaction condition. The reaction involved operational simplicity, metal free oxidation, and wide functional group tolerance as attractive features.
- Sutar, Yogesh B.,Bhagat, Saket B.,Telvekar, Vikas N.
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p. 6768 - 6771
(2016/02/03)
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- Potassium tert-Butoxide-Mediated Amine Acyl Exchange Reaction of N,N-Disubstituted Formamides with Aromatic Carbonyl Derivatives via Sequential C-N Bond Cleavage/Formation: An Approach to Aromatic Amides
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A novel potassium tert-butoxide-mediated amine acyl exchange of N,N-disubstituted formamides with aromatic carbonyl derivatives in a sequential C-N bond cleavage/formation process leading to aromatic amides is described. This methodology tolerates a wide range of aromatic carbonyl compounds, including aromatic aldehydes, acyl chlorides, unactivated esters, and acid anhydrides. The usage of inexpensive and readily available reagents, broad substrate scope, and the simple, mild (50°C) and transition metal-free conditions make this protocol very practical. In addition, a plausible reaction mechanism is proposed on the basis of experimental observations.
- Zhang, Ming-Zhong,Guo, Qing-Hu,Sheng, Wen-Bing,Guo, Can-Cheng
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p. 2855 - 2861
(2015/09/28)
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- Easy access to amides through aldehydic C-H bond functionalization catalyzed by heterogeneous Co-based catalysts
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A novel synthesis strategy for amides by oxidative amidation of aldehydes is developed using a heterogeneous Co-based catalyst. The Co composite was prepared by simple pyrolysis of a Co-containing MOF, to obtain well-dispersed Co nanoparticles enclosed by carbonized organic ligands. The catalysts were characterized by powder X-ray diffraction (PXRD), N2 physical adsorption, atomic absorption spectroscopy (AAS), transmission electron microscopy (TEM), scanning electronic microscopy (SEM), and X-ray photoelectron spectroscopy (XPS). The small Co nanoparticles embedded in the N-doped carbons were highly dispersed with an average size of ca. 7 nm. The Co@C-N materials exhibited significantly enhanced catalytic activity in the oxidative amidation of aldehydes in comparison to those of commercial sources. A series of amides can be easily obtained in good to excellent yields. It was found that the reaction proceeded via radicals under mild conditions, and the carbonyl group in the amide product was from the aldehyde. Moreover, the catalyst could be easily separated by using an external magnetic field and reused several times without significant loss in catalytic efficiency under the investigated conditions. (Chemical Equation Presented).
- Bai, Cuihua,Yao, Xianfang,Li, Yingwei
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p. 884 - 891
(2015/02/19)
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- An efficient method for the preparation of styrene derivatives via Rh(III)-catalyzed direct C-H vinylation
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The development of a method for the Rh(III)-catalyzed direct vinylation of an aromatic C-H bond to give functionalized styrenes in good yield, using vinyl acetate as a convenient and inexpensive vinyl source, is reported. High functional group tolerance is demonstrated for electronically distinct arenes as well as different directing groups. Mechanistic investigation resulted in the characterization of a novel rhodium-metallacycle, which represents the first X-ray structure of a [1,2]-Rh(III)-alkenyl addition adduct.
- Otley, Kate D.,Ellman, Jonathan A.
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supporting information
p. 1332 - 1335
(2015/03/14)
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- Syntheses of amides via iodine-catalyzed multiple sp3 C-H bonds oxidation of methylarenes and sequential coupling with N,N-dialkylformamides
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The oxidative coupling of methylarenes and N,N-dialkylformamides was developed, and the appropriate reaction conditions were established. By using I2 as the catalyst, and tert-butyl hydroperoxide (TBHP) as the oxidant, the reaction provided N,N
- Du, Bingnan,Sun, Peipei
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p. 1176 - 1182
(2014/08/18)
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- Oxidative synthesis of benzamides from toluenes and DMF
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An interesting oxidative procedure for the synthesis of benzamides has been developed through the cleavage of sp3CH bond of methyl arenes with N-substituted formamides. Various benzamides were prepared in low to moderate yields. Even though the
- Feng, Jian-Bo,Wei, Duo,Gong, Jin-Long,Qi, Xinxin,Wu, Xiao-Feng
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supporting information
p. 5082 - 5084
(2015/01/08)
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- Oxidative coupling of methylamine with an aminyl radical: Direct amidation catalyzed by I2/TBHP with HCl
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Oxidative coupling of methylamines with an aminyl radical to construct amides was developed in the presence of an I2/TBHP catalyst under acidic conditions via the two cleavages of the sp3 C-N bond of aryl-methylamines and the sp2 C-N bond of N-substituted formamides respectively. This transition-metal-free protocol provides a novel synthetic tool for the construction of N-substituted amides and a series of arylamides can be easily obtained with good yields. This journal is the Partner Organisations 2014.
- Gao, Lingfeng,Tang, Haoming,Wang, Zhiyong
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supporting information
p. 4085 - 4088
(2014/04/03)
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- Facile preparation of aromatic esters from aromatic bromides with ethyl formate or DMF and molecular iodine via aryllithium
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Various aromatic bromides were treated with n-BuLi and subsequently with ethyl formate, followed by the reaction with ethanol and molecular iodine in the presence of K2CO3 to provide the corresponding aromatic ethyl esters in good yields. Moreover, aromatic bromides could be transformed into the corresponding aromatic methyl esters in good yields by the treatment with n-BuLi and subsequently with DMF, followed by the reaction with methanol, molecular iodine, and K2CO3. Some aromatics could be also converted into the corresponding aromatic esters in good yields by the treatment with n-BuLi, and subsequently with ethyl formate or DMF, followed by the reaction with molecular iodine and K2CO3. The present reactions offer a novel route for the transition-metal-free, carbon-monoxide-free, and therefore environmentally benign one-pot conversion of aromatic bromides and aromatics into aromatic esters.
- Ushijima, Sousuke,Moriyama, Katsuhiko,Togo, Hideo
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experimental part
p. 4701 - 4709
(2012/07/28)
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- A novel method for the one-pot conversion of carboxylic acids to N,N-dimethylamides
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A simple, efficient, and new method has been developed for the preparation of N,N-dimethylamides from carboxylic acids. As described below, treatment of a variety of aromatic carboxylic acids with N,N-dimethylsulfamoyl imidazole or N,N-dimethylsulfamoyl chloride in the presence of a mixture of methanesulfonic acid/phosphorus pentoxide (2:1, v/w) proceeded effectively to afford the corresponding N,N-dimethylamides inmoderate to good yields. Thismethod is easy, rapid, and good yielding for the synthesis of N,N-dimethylamides from carboxylic acids. Iranian Chemical Society 2012.
- Kaboudin, Babak,Haghighat, Hamideh
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p. 951 - 955
(2013/02/23)
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- Direct amidation of alcohols with N-substituted formamides under transition-metal-free conditions
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Go tandem! The first example of the direct amidation of alcohols with N-substituted formamides has been developed. A series of tertiary amides, including the challenging N,N-dimethyl-substituted amides, were obtained in moderate to good yields under transition-metal-free conditions (see scheme). TBHP=tert-butyl hydroperoxide. Copyright
- Xu, Kun,Hu, Yanbin,Zhang, Sheng,Zha, Zhenggen,Wang, Zhiyong
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supporting information; experimental part
p. 9793 - 9797
(2012/09/05)
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- Piperazines as oxytocin agonists
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Disclosed are novel compounds according to general formula I, which have shown OT agonist activity.
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Page/Page column 13
(2010/02/11)
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- Process for preparing 5-aroyl-2,3-dihydro-1H-pyrrolizine-1,1-dicarboxylates (I) and intermediates therefor
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5-Aroyl-2,3-dihydro-1H-pyrrolizine-1,1-dicarboxylates of the formula STR1 are prepared from 2-aroylpyrroles. Hydrolysis and mono-decarboxylation of these compounds affords ketorolac and related compounds.
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