1466-77-9

Upstream product

• 1466-76-8 2-6-dimethoxybenzoic acid 
• 62-53-3 aniline 
• 1989-53-3 2,6-dimethoxybenzoyl chloride 
• 103-71-9 phenyl isocyanate 
• 591-50-4 iodobenzene 
• 77331-14-7 2,6-dimethoxybenzoic acid triethylammonium salt 
• 77331-20-5 C₁₅H₁₈ClN₂O₉P*C₆H₁₅N 
• 103-72-0 phenyl isothiocyanate 

Downstream Products

• 5866-81-9 (2,6-Dimethoxy-benzoyl)-phenyl-carbamic acid isopropyl ester 
• 103-71-9 phenyl isocyanate 
• 690223-22-4 2,6-dimethoxy-cyclohexa-2,5-dienecarboxylic acid phenylamide 

Relevant academic research and scientific papers

A one-pot route to thioamides discovered by gas-phase studies: palladium-mediated CO2 extrusion followed by insertion of isothiocyanates

A new palladium mediated “one pot” synthesis of thioamides from aromatic carboxylic acids (ArCO2H + RNCS → ArC(S)NHR + CO2) was discovered by gas-phase experiments and theoretical studies. Palladium-mediated decarboxylation of aromatic carboxylic acids followed by addition of substituted isothiocyanates leads to the corresponding thioamide derivatives.

Palladium-Mediated CO2 Extrusion Followed by Insertion of Isocyanates for the Synthesis of Benzamides: Translating Fundamental Mechanistic Studies to Develop a Catalytic Protocol

Mechanistic studies of a stoichiometric palladium-mediated ExIn (ExIn = extrusion-insertion) decarboxylative amidation of aromatic carboxylic acids are presented, providing gas-phase and condensed-phase spectroscopic data, as well as theoretical computational evidence for intermediates in a proposed stepwise process. The understanding gained from these mechanistic studies directed the development of a palladium-catalyzed procedure in which benzamides are obtained in good to high yields in a one-pot 30 min microwave irradiation assisted protocol. A combination of experimental data and DFT calculations reveals that certain ligand additives favor the selective formation of benzamides rather than the undesired protodecarboxylation side product.

An efficient magnetic copper ferrite nanoparticle catalysed ligand and solvent free synthesis of N-aryl amide from aldoximes and iodobenzene

A simple, efficient, and environmentally benign method has been reported for the synthesis of N-aryl amides using aldoximes and iodobenzene under ligand free and solvent free conditions and using magnetically separable copper ferrite nanoparticles as catalyst. The catalyst was characterised using XRD, FEG-SEM, EDAX, ICP-AES and TEM and tested for recyclability for up to five cycles.

Benzylamide derivative compound attenuates the ultraviolet B-induced hyperpigmentation in the brownish guinea pig skin

This study evaluated the effects of synthetic benzylamide compound I (2,6-dimethoxy-N-phenylbenzamide) on the ultraviolet B (UV B)-induced hyperpigmentation of the skin. UV B-induced hyperpigmentation was elicited on brownish guinea pig skin according to the method reported by Hideya et al. [Arch Dermatol Res 290 (1998) 375] with minor modifications. A lightening effect was observed following the topical application of compound I on UV-stimulated hyperpigmentation. The skin returned to its original color after treatment with compound I. Fontana-Masson staining indicated that melanin level in the hyperpigmented area was significantly decreased in the compound I-treated animals. However, the number of melanocytes were not changed in the compound I-treated groups using the S-100 stain, which is an immunohistochemical method. In vitro experiments using the cultured melanoma cells showed a 31.7% inhibition of melanin production by compound I at 100μM. In addition, this compound had no effect on the tyrosinase enzyme function. However, it exhibited a catalyzing effect on the dopachrome transformation into 5,6-dihydroxyindole-2-carboxylic acid. Overall, the pigment-lightening effects of the compound I may due to the dopachrome tautomerase stimulation.

NEW ACTIVATION OF CARBOXYLIC ACIDS BY REACTION WITH N,N-BIS-(2-OXO-3-OXAZOLIDINYL) PHOSPHORODIAMIDIC CHLORIDE (ClSPO)

Pentacoordinated and quinquevalent phosphorus intermediates, have been isolated by reaction between the title reagent and carboxylic acids, prior to conversion into amides.