- 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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- Selective Methylation of Amides, N-Heterocycles, Thiols, and Alcohols with Tetramethylammonium Fluoride
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We herein disclose the use of tetramethylammonium fluoride (TMAF) as a direct and selective methylating agent of a variety of amides, indoles, pyrroles, imidazoles, alcohols, and thiols. The method is characterized by operational simplicity, wide scope, and ease of purification. Our computational studies suggest a concerted methylation-deprotonation as the preferred reaction pathway.
- Cheng, Hong-Gang,Pu, Maoping,Kundu, Gourab,Schoenebeck, Franziska
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supporting information
p. 331 - 334
(2019/12/30)
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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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- Synthesizing method of raw nicosulfuron
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The invention provides a synthesizing method of raw nicosulfuron. The method includes: synthesizing N,N-dimethyl nicotinamide, oxidizing the N,N-dimethyl nicotinamide, performing the sulfonylation of2-carbamido-4,6-dimethoxy pyrimidine, and synthesizing the raw nicosulfuron. The synthesizing method is short in synthesizing route, low in cost, high in yield, mild in synthesizing conditions, capable of avoiding the use of high-toxicity and high-pollution raw materials such as phosphorus oxychloride, chlorine and phosgene, green and safe, and capable of achieving industrial production.
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Paragraph 0013; 0024; 0026-0028; 0038; 0040; 0044; 0046
(2018/10/19)
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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 0095; 0096; 0097; 0098; 0099
(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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- Palladium-Catalyzed Aminocarbonylation of Aryl Halides with 2,4,6-Trichloro-1,3,5-triazine/Formamide Mixed Reagent
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In this work, the mixture of formamide and 2,4,6-trichloro-1,3,5-triazine (cyanuric chloride or TCT) is introduced as a new amidating agent in Pd-catalyzed aminocarbonylation of aryl halides. In the presence of a catalytic amount of palladium and TCT/formamide reagent, a range of aryl halides (X = Cl, Br, I) were converted into amides efficiently in N,N-dimethylformamide at 120 °C. The 2,4,6-trichloro-1,3,5-triazine/formamide mixed reagent was found to be an efficient amidating agent in Pd-catalyzed aminocarbonylation of aryl halides. In the presence of this reagent and a catalytic amount of Pd, a range of amides were synthesized by using aryl halides.
- Iranpoor, Nasser,Panahi, Farhad,Roozbin, Fatemeh,Erfan, Soodabeh,Rahimi, Sajjad
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supporting information
p. 1781 - 1787
(2016/04/05)
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- PROCESS FOR PREPARATION OF N,N-DI SUBSTITUTED CARBOXAMIDES
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The present disclosure relates to a single pot process for preparation of a N,N-di substituted carboxamide compounds of formula (I), said process comprising: reacting a carboxylic acid with a di-substituted carbamoyl chloride in presence of an organic tertiary base to obtain the N,N-di substituted carboxamide compounds of formula (I). The process of the present disclosure involves a simple step, and it is energy and time saving process for preparation of N,N-di substituted carboxamides.
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Paragraph 0103-0104
(2015/05/13)
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- PROCESS FOR PREPARATION OF N,N-DI SUBSTITUTED CARBOXAMIDES
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The present disclosure relates to a single pot process for preparation of a N,N-di substituted carboxamide compounds of formula (I), said process comprising: reacting a carboxylic acid with a di-substituted carbamoyl chloride in presence of an organic tertiary base to obtain the N,N-di substituted carboxamide compounds of formula (I). The process of the present disclosure involves a simple step, and it is energy and time saving process for preparation of N, N-di substituted carboxamides.
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Page/Page column 15
(2013/05/22)
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- Preparation of N,N-dimethyl aromatic amides from aromatic aldehydes with dimethylamine and iodine reagents
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Various N,N-dimethyl aromatic amides were obtained in good to moderate yields by the reaction of aromatic aldehydes with aqueous dimethylamine in the presence of molecular iodine or 1,3-diiodo-5,5-dimethylhydantoin (DIH) at room temperature. Under the same conditions and using the same procedure, treatment of aromatic aldehydes and morpholine in the presence of DIH also provided the corresponding N-aroyl morpholines in good to moderate yields. Georg Thieme Verlag Stuttgart · New York.
- Baba, Haruka,Moriyama, Katsuhiko,Togo, Hideo
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experimental part
p. 1175 - 1180
(2012/06/04)
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- Unexpectedly produced 2-tert-butyl-5-(N,N-dimethylcarbamoyl)pyridine from 2-chloro-3-(N,N-dimethylcarbamoyl)-pyridine with a tert-butyl Grignard reagent
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The title compound, C12H18N2O, was obtained by the reaction of 2-chloro-3-(N,N-dimethylcarbamoyl)pyridine with tert-butylmagnesium chloride. The structure was confirmed by NMR spectroscopy and X-ray crystallography.
- Mikata, Yuji,Maesaki, Ryoko
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p. 973 - 975
(2007/10/03)
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- AN ALTERNATIVE PROCEDURE FOR THE ALUMINUM-MEDIATED CONVERSION OF ESTERS TO AMIDES
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A convenient method has been developed for directly converting esters to amides using reagents derived from the reaction of trimethylaluminum with ammonium chloride, methylamine hydrochloride or dimethylamine hydrochloride.
- Levin, Jeremy I.,Turos, Edward,Weinreb, Steven M.
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p. 989 - 994
(2007/10/02)
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