- Activator free, expeditious and eco-friendly chlorination of activated arenes by N-chloro-N-(phenylsulfonyl)benzene sulfonamide (NCBSI)
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N-Chloro-N-(phenylsulfonyl)benzene sulfonamide (NCBSI) has been explored for the first time as a chlorinating reagent for direct chlorination of various activated arenes and heterocycles without any activator. A comparative in-silico study was performed to determine the electrophilic character for NCBSI and commercially available N-chloro reagents to reveal the reactivity on a theoretical viewpoint. The reagent was prepared by an improved method avoiding the use of hazardous t-butyl hypochlorite. This reagent was proved to be very reactive compared to other N-chloro reagents. The precursor of the reagent N-(phenylsulfonyl)benzene sulfonamide was recovered from aqueous spent, which can be recycled to synthesize NCBSI. The eco-friendly protocol was equally applicable for the synthesis of industrially important chloroxylenol as an antibacterial agent.
- Misal, Balu,Palav, Amey,Ganwir, Prerna,Chaturbhuj, Ganesh
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supporting information
(2021/01/04)
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- Transition-metal-free mono- or dinitration of protected anilines
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An amide-assisted arene nitration is presented, and both mono- and dinitration of protected anilines could be effected by using NaNO2 and NaNO3 as the mono- and bisnitrating agents, respectively. This divergent synthesis is transition-metal- and acid-free, and features a broad substrate scope, low cost, and ortho–para selectivity.
- Dai, Enrui,Dong, Ying,Dong, Yongrui,Kong, Rui,Liang, Deqiang,Liu, Guangzhang,Ma, Yinhai,Wu, Qiong
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- Variable noninnocence of substituted azobis(phenylcyanamido)diruthenium complexes
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The synthetic chemistry of substituted 4,4′-azobis(phenylcyanamide) ligands was investigated, and the complexes [{Ru(tpy)(bpy)}2( μ-L)][PF6]2, where L = 2,2′:5,5′-tetramethyl-4,4′-azobis(phenylcyanamido) (Me4adpc2-), 2,2′-dimethyl-4,4′-azobis(phenylcyanamido) (Me2adpc2-), unsubstituted (adpc2-), 3,3′-dichloro-4,4′-azobis(phenylcyanamido) (Cl2adpc2-), and 2,2′:5,5′-tetrachloro-4,4′-azobis(phenylcyanamido) (Cl4adpc2-), were prepared and characterized by cyclic voltammetry and vis-near-IR (NIR) and IR spectroelectrochemistry. The room temperature electron paramagnetic resonance spectrum of [{Ru(tpy)(bpy)}2( μ-Me4adpc)]3+ showed an organic radical signal and is consistent with an oxidation-state description [RuII, Me4adpc?-, RuII]3+, while that of [{Ru(tpy)(bpy)}2( μ-Cl2adpc)]3+ at 10 K showed a low-symmetry RuIII signal, which is consistent with the description [RuIII, Cl2adpc2-, RuII]3+. IR spectroelectrochemistry data suggest that [{Ru(tpy)(bpy)}2( μ-adpc)]3+ is delocalized and [{Ru(tpy)(bpy)}2( μ-Cl2adpc)]3+ and [{Ru(tpy)(bpy)}2( μ-Cl4adpc)]3+ are valence-trapped mixed-valence systems. A NIR absorption band that is unique to all [{Ru(tpy)(bpy)}2( μ-L)]3+ complexes is observed; however, its energy and intensity vary depending on the nature of the bridging ligand and, hence, the complexes oxidation-state description.
- Choudhuri, Mohommad M. R.,Behzad, Mahdi,Al-Noaimi, Mousa,Yap, Glenn P. A.,Kaim, Wolfgang,Sarkar, Biprajit,Crutchley, Robert J.
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supporting information
p. 1508 - 1517
(2015/06/16)
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- ALLOSTERIC MODULATORS OF METABOTROPIC GLUTAMATE RECEPTORS
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Formula (I), and salts thereof, wherein R1, RA2, RA3 and RA4, are defined herein, which have properties for positive allosteric modulation of mGluR-4 receptor sites. Also described are pharmaceutical formulations comprising the compounds of Formula (I) or their salts, and methods of treating Parkinson's disease and related disorders using the same.
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Paragraph 0112
(2013/05/21)
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- ALLOSTERIC MODULATORS OF METABOTROPIC GLUTAMATE RECEPTORS
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Disclosed are compounds of Formula (I), and salts thereof, wherein R1, RA2, RA3 and RA4, are defined herein, which have properties for positive allosteric modulation of mGluR-4 receptor sites. Also described are pharmaceutical formulations comprising the compounds of Formula (I) or their salts, and methods of treating Parkinson's disease and related disorders using the same.
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Paragraph 0112
(2013/05/21)
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- Sodium lauryl sulfate-catalyzed oxidative chlorination of aromatic compounds
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Chlorination of commercially important aromatic compounds using sodium chloride as chlorine source and sodium periodate as oxidant in acidic medium catalyzed by sodium lauryl sulfate (SLS) led to the chloro-substituted aromatics in good yields and purity. Addition of sodium lauryl sulfate led to increased chlorination rate, better yield, excellent purity, and better quality of end product. The advantages of the present method are greater yield, excellent purity, and shorter reaction time at room temperature. Also dichlorinated product can be obtained by increasing the amount of sodium chloride and sodium periodate at slightly higher temperature (40C).
- Mahajan, Tanu,Kumar, Lalit,Dwivedi, K.,Agarwal, D. D.
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p. 3655 - 3663,9
(2020/08/31)
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- The use of sodium chlorate/hydrochloric acid mixtures as a novel and selective chlorination agent
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Sodium chlorate/hydrochloric acid mixtures were used to chlorinate activated arenes and the α-position of ketones. This chlorination method was used to produce selectively mono-, di-, and trichlorinated compounds by controlling the molarity of sodium chlorate. This reagent proved to be much more efficient and easier to handle than chlorine gas.
- Moon, Byung Seok,Choi, Han Young,Koh, Hun Yeong,Chi, Dae Yoon
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experimental part
p. 472 - 476
(2011/12/04)
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- Ammonium nickel sulphate mediated nitration of aromatic compounds with nitric acid
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Aromatic compounds were efficiently nitrated under mild conditions employing ammonium nickel sulphate and nitric acid as a reagent. This procedure works efficiently at room temperature yielding mononitro derivative in fair to good yield with high regioselectivity.
- Tasneem,Ali,Rajanna,Saiparakash
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p. 1123 - 1127
(2007/10/03)
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- Mild, efficient and selective nitration of anilides, non-activated and moderately activated aromatic compounds with ammonium molybdate and nitric acid as a new nitrating agent
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Ammonium molybdate [Mo(VI)] is operationally simple, environmentally safe and inexpensive reagent. Regioselective nitration of anilides, non-activated and moderately activated aromatic compounds could be afforded by employing ammonium molybdate and nitric acid as mild and effective nitrating agent. This procedure works efficiently under reflux conditions to prepare mononitroderivatives of anilides, non-activated and moderately activated aromatic compounds in good to excellent yield with high regioselectivity.
- Sana, Sariah,Rajanna,Ali, Mir Moazzam,Saiprakash
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- Oxidative chlorination of various lodoarenes to (dichloroiodo)arenes with chromium(vi) oxide as the oxidant j
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Chromium(vi) oxide dissolved in a mixture of acetic acid with concentrated hydrochloric acid converts, at or near room temperature, iodoarenes to (dichloroiodo)arenes, in a very simple and efficient procedure.
- Kazmierczak, Pawet,Skulski, Lech,Obeid, Nicolas
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- An Effective Method for Acylation of Weakly Nucleophilic Anilines with Silyl Carboxylates via Mixed Anhydrides
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In the presence of a catalytic amount of active titanium(IV) salt generated in situ from 1 mol of TiCl4 and 2 mol of AgOTf, weakly nucleophilic anilines react under mild conditions with nearly equimolar amounts of silyl carboxylates to afford the corresponding anilides in excellent yields using 4-(trifluoromethyl)benzoic anhydride.The mixed anhydride formed in situ from trimethylsilyl acetate and 4-(trifluoromethyl)benzoic anhydride, a key intermediate of this reaction, was detected by 1H NMR experiment.Further, it was shown that the reaction of the mixed anhydrides and 2-nitroaniline was faster than that of the corresponding homo anhydrides and 2-nitroaniline.
- Miyashita, Mitsutomo,Shiina, Isamu,Mukaiyama, Teruaki
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p. 210 - 215
(2007/10/02)
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- A Convenient Synthesis of Carboxanilides from Silyl Carboxylates and Weakly Nucleophilic Anilines Using p-Trifluoromethylbenzoic Anhydride and a Catalytic Amount of Active Titanium(IV) Salt
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Various carboxanilides are prepared in excellent yields from nearly equimolar amounts of silyl carboxylates and the corresponding weakly nucleophilic anilines under mild conditions by using p-trifluoromethylbenzoic anhydride and a catalytic amount of active titanium(IV) salt.
- Miyashita, Mitsutomo,Shiina, Isamu,Mukaiyama, Teruaki
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p. 1053 - 1054
(2007/10/02)
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- Oxidative chlorination of acetanilides with hydrogen chloride/m-chloroperbenzoic acid/N,N-dimethylformamide system
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The reaction of acetanilides with relevant amounts of HCl and m-chloroperbenzoic acid in DMF at room temperature gave the desired chloro-substituted acetanilides in good yields.
- Chung,Kim,Kim,Ryu
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p. 1917 - 1922
(2007/10/02)
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