3010-82-0Relevant academic research and scientific papers
Room Temperature Hydrolysis of Benzamidines and Benzamidiniums in Weakly Basic Water
Yu, Li-Juan,Cullen, Duncan A.,Morshedi, Mahbod,Coote, Michelle L.,White, Nicholas G.
supporting information, p. 13762 - 13767 (2021/10/12)
Benzamidinium compounds have found widespread use in both medicinal and supramolecular chemistry. In this work, we show that benzamidiniums hydrolyze at room temperature in aqueous base to give the corresponding primary amide. This reaction has a half-life of 300 days for unsubstituted benzamidinium at pH 9, but is relatively rapid at higher pH's (e.g., t1/2 = 6 days at pH 11 and 15 h at pH 13). Quantum chemistry combined with first-principles kinetic modeling can reproduce these trends and explain them in terms of the dominant pathway being initiated by attack of HO- on benzamidine. Incorporation of the amidinium motif into a hydrogen bonded framework offers a substantial protective effect against hydrolysis.
Method for preparing terephthalamide from terephthalic acid
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Paragraph 0046-0112, (2021/06/21)
The invention discloses a method for preparing terephthalamide from terephthalic acid, which comprises the following steps: carrying out esterification reaction on terephthalic acid and alcohol, and discharging by-product water generated by the reaction out of the reaction system; introducing ammonia gas into the esterification liquid to be ammonolyzed, and carrying out ammonolysis reaction to obtain a reaction container (marked as a reaction container I) filled with ammonolysis liquid containing high-concentration ammonia gas; connecting the reaction container I with a reaction container (marked as a reaction container II) filled with a next batch of esterification liquid to be ammonolyzed, so as to recover excessive ammonia gas; and cooling the ammonolysis liquid containing the low-concentration ammonia gas in the reaction container I, conducting filtering, and washing and drying a filter cake to obtain terephthalamide. According to the invention, terephthalic acid is subjected to esterification and ammonolysis to produce terephthalamide, the main byproduct in the reaction process is water, and the green production concept is met.
A PROCESS FOR THE PREPARATION OF 4-CYANOBENZOYL CHLORIDES
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Page/Page column 11-12, (2021/10/22)
The present invention relates to a process for the preparation of 4-cyanobenzoyl chlorides of formula I through reaction of compounds of formula II with a chlorinating agent.
Half-Sandwich Iridium Complexes for the One-Pot Synthesis of Amides: Preparation, Structure, and Diverse Catalytic Activity
Fan, Xiao-Nan,Deng, Wei,Liu, Zhen-Jiang,Yao, Zi-Jian
, p. 16582 - 16590 (2020/11/13)
Several types of air-stable N,O-coordinate half-sandwich iridium complexes containing Schiff base ligands with the general formula [Cp*IrClL] were synthesized in good yields. These stable iridium complexes displayed a good catalytic efficiency in amide synthesis. A variety of amides with different substituents were obtained in a one-pot procedure with excellent yields and high selectivities through the amidation of aldehydes with NH2OHHCl and nitrile hydration under the catalysis of complexes 1-4. The excellent and diverse catalytic activity, mild conditions, broad substance scope, and environmentally friendly solvent make this system potentially applicable in industrial production. Half-sandwich iridium complexes 1-4 were characterized by NMR, elemental analysis, and IR techniques. Molecular structures of complexes 2 and 3 were confirmed by single-crystal X-ray analysis.
Preparation method of aromatic amide compound
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Paragraph 0056-0057, (2020/07/15)
The present invention provides a preparation method of an aromatic amide compound. In an organic solvent, under the effect of a catalyst, an aromatic acid compound and an amine source are subjected toa dehydration reaction to obtain the aromatic amide compound, wherein the aromatic acid compound is an aromatic acid, a substituted aromatic acid, a heterocyclic aromatic acid or a substituted heterocyclic aromatic acid; and the substituent group of amide is any substituent group of H, a C1-C8 straight-chain alkyl or branched-chain alkyl group, a benzene ring or an aromatic ring. The aromatic amide compound is an important chemical intermediate, and the synthesis method is mild in reaction condition and high in yield.
Ru-based complexes as heterogeneous potential catalysts for the amidation of aldehydes and nitriles in neat water
Arafa, Wael Abdelgayed Ahmed
supporting information, p. 1056 - 1064 (2020/11/09)
Five novel heterogeneous mononuclear complex-anchored Ru(III) have been efficiently sono-synthesized and characterized by utilizing several analytical techniques. The assembled complexes could be utilized as effective, robust and recyclable (up to eight consecutive runs) catalysts for one-pot transformation of a vast array of nitriles and aldehydes to primary amides in H2O under aerobic conditions. Moreover, some unreported di- and tetra-amide derivatives were obtained also under the optimal conditions. The results of ICP/OES analysis demonstrated that there is no detected leaching of the recycled catalyst, which suggests the real heterogeneity of the present protocol. The present Ru-complexes exhibited superiority compared to other reported catalysts for amide preparation in terms of low catalyst load, short reaction time, low operating temperature, no hazardous additives required, and high values of TON (990) and TOF (1980 h11).
Hydration of nitriles using a metal-ligand cooperative ruthenium pincer catalyst
Guo, Beibei,Otten, Edwin,De Vries, Johannes G.
, p. 10647 - 10652 (2019/12/02)
Nitrile hydration provides access to amides that are important structural elements in organic chemistry. Here we report catalytic nitrile hydration using ruthenium catalysts based on a pincer scaffold with a dearomatized pyridine backbone. These complexes catalyze the nucleophilic addition of H2O to a wide variety of aliphatic and (hetero)aromatic nitriles in tBuOH as solvent. Reactions occur under mild conditions (room temperature) in the absence of additives. A mechanism for nitrile hydration is proposed that is initiated by metal-ligand cooperative binding of the nitrile.
Transfer Hydration of Dinitriles to Dicarboxamides
Naka, Hiroshi,Naraoka, Asuka
supporting information, p. 1977 - 1980 (2019/10/22)
We present a robust method for double transfer hydration of dinitriles to afford diamides. The transfer hydration of 1, n -dinitriles (n = 1-6) proceeds smoothly in the presence of a palladium(II) catalyst with acetamide as a water donor, affording the corresponding diamides in moderate to high yields, without involving significant side reactions such as monohydration or cyclization. The equilibrium was shifted in the forward direction by removing coproduced acetonitrile under reduced pressure.
Trash to treasure: Eco-friendly and practical synthesis of amides by nitriles hydrolysis in WepPA
Sun, Yajun,Jin, Weiwei,Liu, Chenjiang
supporting information, (2019/11/11)
The hydration of nitriles to amides in a water extract of pomelo peel ash (WEPPA) was realized with moderate to excellent yields without using external transition metals, bases or organic solvents. This reaction features a broad substrate scope, wide functional group tolerance, prominent chemoselectivity, and good reusability. Notably, a magnification experiment in this bio-based solvent at 100 mmol further demonstrated its practicability.
Ionic liquid catalysed aerobic oxidative amidation and thioamidation of benzylic amines under neat conditions
Joshi, Abhisek,Kumar, Rahul,Semwal, Rashmi,Rawat, Deepa,Adimurthy, Subbarayappa
supporting information, p. 962 - 967 (2019/03/11)
Tetrabutylammonium hydroxide (TBAOH) was discovered as a highly efficient and green catalyst for aerobic oxidation of the α-methylene carbon of primary amines as well as benzylic groups into the corresponding amides and ketones under neat conditions. We described herein, ionic liquid TBAOH catalysed aerobic oxidation of benzyl amines to benzamides and with elemental sulfur; the corresponding benzylbenzothioamides were obtained under metal-free, oxidant-free and base-free conditions. Applicability at the gram scale for the synthesis of the desired amides/ketones is also demonstrated with the present protocol.
