2433-21-8Relevant articles and documents
Copper-catalyzed amidation of benzoic acids using tetraalkylthiuram disulfides as amine sources
Zeng, Meng-Tian,Xu, Wan,Liu, Min,Liu, Xing,Chang, Cai-Zhu,Zhu, Hui,Dong, Zhi-Bing
supporting information, p. 1434 - 1440 (2017/08/16)
A facile method for the copper-catalyzed synthesis of N-substituted benzamides was explored. In the presence of CuBr and di-tert-butyl peroxide, various N-substituted benzamides were prepared through amidation of benzoic acid by using commercially available and cheap tetraalkylthiuram disulfides as amine sources. With this protocol, a series of 14 N-substituted benzamides were furnished in good to excellent yields. The broad substrate scope and good to excellent yield show its practical synthetic value in organic synthesis.
Acid anhydrides and the unexpected N,N-diethylamides derived from the reaction of carboxylic acids with Ph3P/I2/Et3N
Phakhodee, Wong,Duangkamol, Chuthamat,Wangngae, Sirilak,Pattarawarapan, Mookda
supporting information, p. 325 - 328 (2016/01/12)
The formation of acid anhydrides from the phosphorous-mediated activation of carboxylic acids was investigated. Under various systems, activation of benzoic acid in the presence of base led to the formation of benzoic anhydride at different rates depending on the reactivity of the reagents. Using the Ph3P-I2/Et3N combination, most aryl acids were converted into the corresponding anhydrides in high yields within 5-10 min. However, for nitro-substituted derivatives, unexpectedly, N,N-diethylamides were isolated without anhydride formation. These results indicated the pronounced effect of substituents in governing these potential side reactions which can significantly affect the yields of acylation reactions promoted by phosphonium species.
Ozone-mediated Nitration of Benzoic Acid, its Alkali and Alkali-earth Metal Salts, Ester, Acid Chloride, Nitrile and Amide with Nitrogen Dioxide
Suzuki, Hitomi,Tomaru, Jun-ichiro,Murashima, Takashi
, p. 2413 - 2416 (2007/10/02)
The title compounds except for the amide are smoothly nitrated with nitrogen dioxide at low temperatures in the presence of ozone, giving a mixture of the corresponding nitro derivatives mainly composed of the meta isomer in high yield.The nitration products are generally rich in the ortho isomer compared with those obtained by the conventional procedures based on the use of nitric acid or mixed acid.Under similar conditions, benzamide readily loses nitrogen to afford benzoic acid and its nitro derivatives, while N,N-diethylbenzamide is converted into a mixture of three isomeric nitro derivatives with an approximate ratio ortho:meta:para = 3:3:4.