3360-81-4

Usage

InChI:InChI=1/C14H14N2O5S/c1-10-3-6-12(7-4-10)22(19,20)15-13-8-5-11(21-2)9-14(13)16(17)18/h3-9,15H,1-2H3

Upstream product

• 1150-26-1 N-(4-Methoxy-phenyl)-4-methyl-benzenesulfonamide 
• 7697-37-2 nitric acid 
• 104-94-9 4-methoxy-aniline 
• 98-59-9 p-toluenesulfonyl chloride 
• 96-96-8 4-methoxy-2-nitroaniline 

Downstream Products

• 674815-15-7 toluene-4-sulfonic acid-[N-(3-diethylamino-propyl)-4-methoxy-2-nitro-anilide] 
• 304913-71-1 toluene-4-sulfonic acid-(4-methoxy-2-nitro-N-propyl-anilide) 
• 96-96-8 4-methoxy-2-nitroaniline 
• 854638-14-5 toluene-4-sulfonic acid-[N-(2-diethylamino-ethyl)-4-methoxy-2-nitro-anilide] 
• 3360-80-3 toluene-4-sulfonic acid-(4-methoxy-N-methyl-2-nitro-anilide) 
• 13017-31-7 N-(2-Morpholino-ethyl)-N-(p-toluolsulfonyl)-2-nitro-4-methoxy-anilin 
• 7288-56-4 N-(4-chlorobenzyl)-N-<(4-methylphenyl)sulfonyl>-2-nitro-4-methoxyaniline 
• 16058-88-1 N-(2-Bromoethyl)-N-tosyl-4-methoxy-2-nitraniline 
• 86439-27-2 N-(2-hydroxyethyl)-4'-methoxy-2'-nitrotosylanilide 
• 7187-24-8 N¹-(4-chlorobenzyl)-4-methoxybenzene-1,2-diamine 
• 136122-75-3 4-[1-(4-Chloro-benzyl)-5-methoxy-1H-benzoimidazol-2-yl]-3,3-dimethyl-butyric acid ethyl ester 
• 86439-32-9 9-methoxy-2-methyl-6-tosyl-5,6-dihydro-4H-3,1,6-benzoxadiazocine 
• 86439-30-7 ethyl N-<2--4-methoxyphenyl>acetamidate 
• 86439-31-8 1-acetyl-2-ethoxy-9-methoxy-2-methyl-6-tosyl-1,4,5,6-tetrahydro-2H-3,1,6-benzoxadiazocine 

Relevant academic research and scientific papers

Triple Mode of Alkylation with Ethyl Bromodifluoroacetate: N, or O-Difluoromethylation, N-Ethylation and S-(ethoxycarbonyl)difluoromethylation

In this report, we have explored a triple mode of chemical reactivity of ethyl bromodifluoroacetate. Typically, bromodifluoroacetic acid has been used as a difluorocarbene precursor for difluoromethylation of soft nucleophiles. Here we have disclosed nucleophilicity and base dependent divergent chemical reactivity of ethyl bromodifluoroacetate. It furnishes lithium hydroxide and cesium carbonate promoted difluoromethylation of tosyl-protected aniline and electron-deficient phenols respectively. Interestingly, switching the base from lithium hydroxide to 4-N,N-dimethylamino pyridine (DMAP) tosyl-protected anilines afforded the corresponding N-ethylation product. Whereas, highly nucleophilic thiophenols furnished the corresponding S-carboethoxydifluoromethylation product via a rapid SN2 attack to the bromine atom prior to the ester hydrolysis. This mechanistic divergence was established through several control experiments. It was revealed that difluoromethylation reaction proceeds through a tandem in situ ester hydrolysis/decarboxylative-debrominative difluorocarbene formation and subsequent trapping by the soft nucleophile-NHTs or electron-deficient phenolic ?OH groups. In the presence of DMAP the hydrolysis of the ester is perturbed instead a nucleophilic attack at the ethyl moiety provides the N-ethylation product. Hence, besides the development of a practical base-promoted N-difluoromethylation of amines and electron-deficient phenols, divergent reactivity pattern of inexpensive and user-friendly ethyl bromodifluoroacetate has been explored. (Figure presented.).

Copper-catalyzed mild nitration of protected anilines

A practical copper-catalyzed direct nitration of protected anilines, by using one equivalent of nitric acid as the nitrating agent, has been developed. This procedure features mild reaction conditions, wide structural scope (with regard to both N-protecting group and arene substitution), and high functional-group tolerance. Dinitration with two equivalents of nitric acid is also feasible. Practical and reliable: A Cu-catalyzed selective nitration of para- and ortho-substituted aniline derivatives by using one equivalent of HNO3 has been developed that produces water as the only stoichiometric byproduct (see scheme; PG=protecting group). This method is compatible with strongly electron-deficient substrates, enabling dinitration (by using 2.0 equiv of HNO3). This method allows for a rapid access to relevant nitrogen-containing heterocyclic architectures.

Direct oxidative nitration of aromatic sulfonamides under mild conditions

A direct nitration of aromatic sulfonamides using sodium nitrite as the nitrating agent has been developed. The reaction shows typically mono-substitution selectivity and can be enlarged to the gram scale with good yield.

Chemoselective nitration of aromatic sulfonamides with tert-butyl nitrite

A methodology for the efficient conversion of aromatic sulfonamides into their mono-nitro derivatives using tert-butyl nitrite is reported. The reaction exhibits a high degree of chemoselectivity for sulfonamide functionalized aryl systems, even in the presence of other sensitive or potentially reactive functionalities.

Synthesis and Structure - Activity Relationships of Novel Benzimidazole and Imidazopyridine Acid Derivatives as Thromboxane A2 Receptor Antagonists

A series of 1-benzylbenzimidazole and 3-benzylimidazopyridine substituted in the 2-position by an alkanoic or mercaptoalkanoic acid chain was synthesized for evaluation as potential thromboxane A2/prostaglandin H2 (TXA2/PGH2) receptor antagonists.T

AZABENZIMIDAZOLE DERIVATIVES WHICH ARE THROMBOXANE RECEPTOR ANTAGONISTS

The present invention relates to the derivatives of the formula STR1 in which: A is an aromatic ring or a nitrogen heterocycle;X 1, X 2, X 3 and X 4 are independently a hydrogen atom, a halogen atom, a lower alkyl radical, a C. sub.3-C 7 cycloalkyl

BENZIMIDAZOLE AND AZABENZIMIDAZOLE DERIVATIVES WHICH ARE THROMBOXANE RECEPTOR ANTAGONISTS, THEIR METHODS OF PREPARATION

The present invention relates to the derivatives of the formula STR1 where the substituents are defined in the specification. These compounds possess thromboxane receptor antagonist properties.

Noval benzimidazole and azabenzimiazole derivatives which are thromboxane receptor antagonists, their methods of preparation and pharmaceutical compositions in which they are present

The present invention relates to the derivatives of the formula STR1 in which: A is an aromatic ring or a nitrogen heterocycle;X 1, X 2, X 3 and X 4 are independently a hydrogen atom, a halogen atom, a lower alkyl radical, an alkoxy radical, an alkylthio