2563-97-5

Usage

Purification Methods

Crystallise the anilide from *benzene or 90% EtOH (m 93.5-95.5o). [Sukornick Org Synth Coll Vol V 1074 1973, Beilstein 12 H 224, 12 I 193, 12 II 142, 12 III 464, 12 IV 377.]

InChI:InChI=1/C8H6Cl3NO/c9-8(10,11)7(13)12-6-4-2-1-3-5-6/h1-5H,(H,12,13)

Upstream product

• 25252-86-2 2,2,2-trichloro-N-phenylacetimidoyl chloride 
• 157252-21-6 Thymyl trichloroacetate 
• 62-53-3 aniline 
• 60-29-7 diethyl ether 
• 76-02-8 trifluoroacetyl chloride 
• 103-84-4 Acetanilid 
• 76-03-9 trichloroacetic acid 
• 369-57-3 benzenediazonium tetrafluoroborate 
• 545-06-2 trichloroacetonitrile 
• 4124-31-6 trichloroacetic acid anhydride 
• 27771-75-1 aniline; trichloroacetate 
• 116-16-5 1,1,1,3,3,3-hexachloro-propan-2-one 
• 67-56-1 methanol 
• 2563-99-7 N-phenyl-2,2-dichloroacetamide 

Downstream Products

• 23326-83-2 N-(2-nitrophenyl)-2,2,2,-trichloroacetamide 
• 4306-32-5 N-(4-nitrophenyl)-2,2,2,-trichloroacetamide 
• 620-81-5 N,N'-Diphenyloxamid 
• 5255-95-8 3-phenyl-5-p-tolyloxymethyl-oxazolidin-2-one 
• 5255-99-2 5-naphthalen-2-yloxymethyl-3-phenyl-oxazolidin-2-one 
• 1226-26-2 5-phenoxymethyl-3-phenyloxazolidin-2-one 
• 5512-78-7 2,2-dichloro-N-phenylacetimidoyl chloride 
• 25252-86-2 2,2,2-trichloro-N-phenylacetimidoyl chloride 
• 5255-92-5 5-(4-nitro-phenoxymethyl)-3-phenyl-oxazolidin-2-one 
• 5255-97-0 3-phenyl-5-o-tolyloxymethyl-oxazolidin-2-one 
• 5255-93-6 methyl 4-(3-phenyl-2-oxo-5-oxazolidinyl)methoxybenzoate 
• 13797-22-3 methyl N-phenyloxamate 
• 2603-10-3 N-phenyl methyl carbamate 
• 62-53-3 aniline 

Relevant academic research and scientific papers

An unsymmetrical covalent organic polymer for catalytic amide synthesis

Herein, we present the first report on the Covalent Organic Polymer (COP) directed non-classical synthesis of an amide bond. An economical route has been chosen for the synthesis of APC-COP using p-aminophenol and cyanuric chloride. APC-COP acts as a smart, valuable and sustainable catalyst for efficient access to the amide bond under mild conditions at room temperature in 30 min. APC-COP exhibits selectivity towards carboxylic acids over esters. The key features of this protocol involve the variety of parameters, viz. wider substrate scope, no use of additive and recyclability, which makes this approach highly desirable in gramscale synthesis. Moreover, we have shown the practical utility of the present method in the catalytic synthesis of paracetamol.

Synthetic method of anesthetic analgesic drug

The invention discloses a synthetic method of an anesthetic analgesic drug. According to the synthetic method, 4-piperidinecarboxylic acid is used as a raw material and subjected to alkylation, bromination, methylation, acylation and the like to prepare the anesthetic analgesic drug. The method avoids the usage of highly toxic cyanide, so the safety and controllability of operation are improved; the method avoids an elimination reaction in reaction process, thereby accelerating reaction speed and shortening reaction time; and the method reduces reaction temperature, shortens the reaction time,and is more suitable for industrial production.

Direct synthesis of N-arylamides via the coupling of aryl diazonium tetrafluoroborates and nitriles under transition-metal-free conditions

The direct synthesis of N-arylamides via the coupling of aryl diazonium tetrafluoroborates and nitriles under transition-metal-free conditions has been developed. The reported protocol is practical and represents an efficient method to produce functionalized amides in moderate to good yields.

A to aryl diazonium tetrafluoroborate salts with a nitrile preparation machine acid radical amine compounds (by machine translation)

The invention provides a high-efficiency, high-selective synthesis of different substituted functional group containing organic amide compound, it adopts the cuprous iodide as a catalyst, in order to aryl diazonium tetrafluoroborate salts compounds and organic nitrile compound as the reaction substrate, the reaction system by adding the organic solvent, water and alkali. The advantage of this method: cheap and easily obtained catalyst; the substrate has a high applicability; mild reaction conditions, safe and reliable; the resulting target product selectivity is close to 100%, yield is as high as 90% or more. The method solves the traditional synthetic organic amide compound of rigorous reaction conditions, the reaction selectivity is poor, the experimental procedure is complicated, the productivity is low and needs to be used for the environment of a harmful reagent and the like, it has good industrial application prospect. The invention also provides a corresponding different substituted functional group containing organic amide compound. (by machine translation)

Efficient partial hydrogenation of trichloromethyl to gem-dichloromethyl groups in platinum on carbon-catalyzed system

While gem-dichloromethyl groups can be directly synthesized by the mono-dechlorination of the corresponding trichloromethyl groups, the suppression control of the over-reduction to form chloromethyl or methyl functionalities is quite difficult. We have established the efficient and widely applicable mono-dechlorination method of the trichloromethyl groups to form the corresponding gem-dichloromethyl groups using platinum on carbon in dimethylacetamide as a specific solvent at 25 °C under a hydrogen atmosphere. The mono-dechlorination of the α,α,α- trichloromethylcarbonyl groups smoothly proceeded by the use of platinum on carbon as a catalyst in a highly chemoselective manner, while the efficient mono-dechlorination of the alkyl- and aryl-trichloromethyl groups required the combined use of Bu3SnH.

Synthesis and antibacterial activities of pleuromutilin derivatives containing aryl urea groups

A series of novel pleuromutilin derivatives containing aryl urea groups was synthesized and their antibacterial activities were evaluated in vitro against S. aureus ATCC 26113, S.aureus SC, S. albus ATCC 8799 and P. aeruginosa ATCC 27853. Most of compound

Platinum on carbon-catalyzed precise reduction control of trichloromethyl to Geminal-dichloromethyl groups

Geminal-dichloromethyl derivatives could be efficiently synthesized by the highly chemoselective platinum on carbon-catalyzed mono-dechlorination of trichloromethyl substrates in dimethylacetamide (DMA) as a specific solvent at 25 °C under a hydrogen atmosphere. Copyright

Synthesis and characterization of N-acylaniline derivatives as potential chemical hybridizing agents (CHAs) for wheat (Triticum aestivum L.)

Induction of male sterility by deployment of chemical hybridizing agents (CHAs) are important in heterosis breeding of self-pollinated crops like wheat, wherein the male and female organs are in the same flower. Taking a lead from the earlier work on rice, a total of 25 N-acylanilines comprising of malonanilates, acetoacetanilides, and acetanilides (including halogenated acetanilides) were synthesized and screened as CHAs on three genotypes of wheat, viz., PBW 343, HD 2046, and HD 2733 at 1500 ppm in the winter of 2001-2002. The N-acylanilines containing variations at the acyl and aromatic domain were synthesized by condensation of substituted anilines with appropriate diesters, acid chlorides, or monoesters. The test compounds with highly electronegative groups such as F/Br at the para position of the aryl ring were identified as the most potent CHAs, causing higher induction of male sterility. A variation of N-substitution at the side chain generally furnished analogues like 4′-fluoroacetoacetanilide (7) and ethyl 4′-fluoromalonanilate (1), which induced 89.12 and 84.66% male sterility, respectively, in PBW 343. Among halogenated acetanilides, the increasing number of chlorine atoms in the side chain led to an increase in the activity of 4′-fluoro (23) and 4′-bromo (24) derivatives of trichoroacetanilides, which induced >87% male sterility. Quantitative structure-activity relationship (QSAR) models indicated the positive contributions of the field effect exemplified by the Swain-Lupton constant (Fp) and negative contributions of the Swain-Lupton resonance constant (R) for the aromatic substitution. The positive influences of parachor (P) for the acyl domain have been underlined. These leads will be significant in explaining the CHA fit in the macromolecular receptor site. The CHAs appeared to act by causing an imbalance in the acid-base equilibrium in pollen mother cells resulting in dissolution of the callose wall by premature callase secretion.

A novel synthesis of isocyanates and ureas via β-elimination of haloform

A novel synthesis of isocyanates via base-induced β-elimination of haloform from N-monosubstituted trihaloacetamides is described. The rate of reaction exhibits a strong dependence on the nature of the trihalomethyl group. Thus, while the reaction of tribromoacetamides proceeds at room temperature and the reaction of trichloroacetamides requires heating in polar solvents, no reaction could be observed for any of the corresponding trifluoro derivatives. This novel β-elimination of haloform from stable and readily available trihaloacetamides was applied to a 'one-pot' synthesis of ureas which avoids the use of phosgene and isolation of isocyanates.

Ozone-mediated Reaction of Anilides and Phenyl Esters with Nitrogen Dioxide: Enhanced Ortho-reactivity and Mechanistic Implications

In the presence of ozone, anilides 1 can be nitrated rapidly with nitrogen dioxide in chloroform at 0 deg C to give a high proportion of ortho-nitro derivatives (ortho:para = 1.2-4.4) in good yields.The phenyl esters 15 can be similarly nitrated on the aromatic ring without significant cleavage of the ester bond, giving a mixture of isomeric nitro derivatives in which the ortho-isomer predominantes (ortho:para = 1.1-1.5).The oridin of the enhanced ortho reactivity is discussed in terms of an electron-transfer process involving the nitrogen trioxide as initial electrophile.