17518-50-2

Usage

Chemical Properties

Off-white to beige crystalline powder

InChI:InChI=1/C14H13NS/c15-14(16)13(11-7-3-1-4-8-11)12-9-5-2-6-10-12/h1-10,13H,(H2,15,16)

Upstream product

• 71-43-2 benzene 
• 947-91-1 Diphenylacetaldehyde 
• 947-89-7 diphenylacetaldehyde imine 
• 4695-13-0 2,2-diphenylacetamide 
• 22259-83-2 2-chloro-2-phenylacetonitrile 
• 5798-79-8 bromo-phenyl-acetonitrile 
• 86-29-3 Diphenylacetonitrile 

Downstream Products

• 101279-63-4 2-benzhydryl-4,5-dihydro-1H-imidazole 
• 1747-72-4 2-benzhydrylidene-thiazolidine-4,5-dione 
• 77358-45-3 Diphenylthioacetylisocyanat 
• 77358-56-6 6-Benzhydryl-3-isopropyl-2-phenyl-2,3-dihydro-4H-1,3,5-thiadiazin-4-on 
• 77358-68-0 6-Benzhydryl-3-(diphenylthioacetyl)-2H-1,3,5-thiadiazin-2,4(3H)-dion 
• 352563-77-0 C₂₂H₁₉NOS 
• 1206549-70-3 2-benzhydryl-6-nitrothiazolo[5,4-b]pyridine 

Relevant academic research and scientific papers

Metal-free, one-pot oxidative conversion of aldehydes to primary thioamides in aqueous media

One-pot tandem reactions of a variety of aldehydes with aqueous ammonia, molecular iodine, and O,O-diethyl dithiophosphoric acid readily afford the corresponding primary thioamides. This is an inexpensive, practical, and metal-free way of accessing various thioamides from aldehydes in aqueous media. The pure products are obtained simply by filtration followed by successive washing with aqueous sodium thiosulfate and water. [Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications for the following free supplemental resource(s): Full experimental and spectral details.]

Stereoelectronic effects dictate molecular conformation and biological function of heterocyclic amides

Heterocycles adjacent to amides can have important influences on molecular conformation due to stereoelectronic effects exerted by the heteroatom. This was shown for imidazole- and thiazole-amides by comparing low energy conformations (ab initio MP2 and DFT calculations), charge distribution, dipole moments, and known crystal structures which support a general principle. Switching a heteroatom from nitrogen to sulfur altered the amide conformation, producing different three-dimensional electrostatic surfaces. Differences were attributed to different dipole and orbital alignments and spectacularly translated into opposing agonist vs antagonist functions in modulating a G-protein coupled receptor for inflammatory protein complement C3a on human macrophages. Influences of the heteroatom were confirmed by locking the amide conformation using fused bicyclic rings. These findings show that stereoelectronic effects of heterocycles modulate molecular conformation and can impart strikingly different biological properties.

Efficient and green protocol for the synthesis of thioamides in C 6 (mim)2Cl2 as a dicationic ionic liquid

A simple, efficient, facile and eco-friendly process for the synthesis of thioamides from nitriles using 1,6-bis(3methylimidazolium-1-yl)hexane chloride [C6(mim)2Cl2] as a dicationic ionic liquid (DIL) was developed. The ionic liquid was easily separated from the reaction mixture and was recycled at least four times without any loss of its activity.

Phosphorus pentasulfide: A mild and versatile reagent for the preparation of thioamides from nitriles

A simple, efficient, and new method has been developed for the synthesis of thioamides from nitriles. The reaction of a variety of aromatic and aliphatic nitriles in the presence of phosphorus pentasulfide afforded the corresponding thioamides in high yields. This method is easy, rapid, and high-yielding for the synthesis of thioamides from nitriles. Georg Thieme Verlag Stuttgart.

Tricyclic compounds, their production and use

A compound of the formula: wherein R1 is H or a substituent; m is 1-3; Ar is an aromatic group which may be substituted; X is a bond or a divalent straight-chain group having 1-6 atoms which may be substituted; Y is —S—, —O—, or —N(R2— (R2 is H or a substituent group), Z is —N= or —C(R3)= (R3 is H or a hydrocarbon group), ring A is a benzene ring; ring B is a 5- to 7-membered ring which may be substituted, or a salt thereof is useful for eliciting a prostaglandin I2 receptor agonistic effect.

Histamine H1 receptor ligands - Part II. Synthesis and in vitro pharmacology of 2-[2-(phenylamino)thiazol-4-yl]ethanamine and 2-(2-benzhydrylthiazol-4-yl)ethanamine derivatives

New 2-[2-(phenylamino)thiazol-4-yl]ethanamine and 2-(2-benzhydrylthiazol-4-yl)ethanamine derivatives were prepared and tested in vitro as H1 receptor antagonists. The compounds with 2-phenylamino substitution with meta-halide substituents at the phenyl ring, showed weak H1-antagonistic activity (pA2: 4.62-5.04) and this activity was completely lost in the case of meta-methyl substituent (pA2 : 4). When the phenylamino group was replaced by benzhydryl groups of classic antihistamines, the resulting compounds exhibited slightly improved H1-antagonistic activity (at the meta-position pA2: 6.38-6.15; at the para-position pA2: 6.04-5.87).