63547-24-0

Usage

Uses

Used in Pharmaceutical Industry:
2-Benzhydrylsulphinylacetic acid is used as a pharmaceutical intermediate for the synthesis of various drugs and active pharmaceutical ingredients. Its unique chemical structure allows it to be a versatile building block in the development of new medications.
Used in Research and Development:
2-Benzhydrylsulphinylacetic acid is utilized in research and development for studying its chemical properties, reactivity, and potential applications in various fields, including medicinal chemistry and drug discovery.

Upstream product

• 63547-22-8 (benzhydrylthio)acetic acid 
• 118286-19-4 (diphenylmethyl)(ethyl acetate)sulfoxide 
• 91-01-0 1,1-Diphenylmethanol 
• 79-11-8 chloroacetic acid 
• 857228-83-2 (Diphenylmethyl)thioacetic acid 
• 64-19-7 acetic acid 
• 68524-30-1 2-(diphenylmethylthio)acetamide 
• 879327-72-7 sodium 2-[(diphenylmethyl)sulfinyl]acetate 

Downstream Products

• 1410075-34-1 2-benzyhydrylsulfinyl-N-(furan-2-ylmethyl)acetamide 
• 1410075-32-9 2-benzyhydrylsulfinyl-N-(4-dimethylaminophenyl)acetamide 
• 1410075-29-4 2-benzyhydrylsulfinyl-N-(4-ethylphenyl)acetamide 
• 1388019-02-0 2-benzyhydrylsulfinyl-N-phenylacetamide 
• 1410075-25-0 2-benzyhydrylsulfinyl-N-[3-(2-oxopyrrolidin-1-yl)propyl]acetamide 
• 1410075-23-8 2-(benzhydrylsulfinyl)-N-((tetrahydrofuran-2-yl)methyl)acetamide 
• 1410075-22-7 2-benzyhydrylsulfinyl-N-cyclohexylacetamide 
• 1410075-18-1 N-allyl-2-benzyhydrylsulfinylacetamide 
• 1410075-16-9 2-benzyhydrylsulfinyl-N-tetradecylacetamide 
• 1410075-15-8 2-benzyhydrylsulfanyl-N-decylacetamide 
• 90280-08-3 2-benzyhydrylsulfinyl-N-(furan-2-ylmethyl)acetamide 
• 1253944-55-6 2-(benzhydrylsulfinyl)-1(N-morpholino)ethanone 
• 949092-13-1 (S)-modafinic acid*(S)-α-methylbenzylamine 
• 112245-25-7 2-(benzhydrylsulfinyl)acetic acid (-)-α-methylbenzylamine 

Relevant academic research and scientific papers

Selective synthesis of sulfoxides and sulfonesviacontrollable oxidation of sulfides withN-fluorobenzenesulfonimide

A practical and mild method for the switchable synthesis of sulfoxides or sulfonesviaselective oxidation of sulfides using cheapN-fluorobenzenesulfonimide (NFSI) as the oxidant has been developed. These highly chemoselective transformations were simply achieved by varying the NFSI loading with H2O as the green solvent and oxygen source without any additives. The good functional group tolerance makes the strategy valuable.

Metal- and additive-free oxygen-atom transfer reaction: an efficient and chemoselective oxidation of sulfides to sulfoxides with cyclic diacyl peroxides

Metal- and additive-free oxidation of a series of sulfides/thioketones has been achieved using cyclic diacyl peroxides as mild oxygen sources. This protocol features simple manipulation, high chemo- and diastereoselectivity, and a broad substrate scope (up to 42 examples), tolerates many common functional groups, and is scalable and applicable to the late-stage sulfoxidation strategy. A preliminary mechanistic study by quantum mechanical calculations suggests that a single two-electron transfer process is energetically more favorable, and indicates the reactivity of cyclic diacyl peroxides distinct from conventional acyclic acyl peroxides.

Vanadium–Schiff base complex-functionalized SBA-15 as a heterogeneous catalyst: synthesis, characterization and application in pharmaceutical sulfoxidation of sulfids

VO2(picolinichydrazone) complex as a catalyst was stabilized on a SBA-15 mesoporous silica as a catalytic support by using (3-chloropropyl)triethoxysilane as a connector. SBA-15 is nanoporous and has a high ratio of surface area to volume. The immobilization of a metal–Schiff base complex to the surface area of SBA-15 can improve its catalytic effects by increasing the catalytic surface area. Unlike homogeneous catalysts, heterogeneous catalysts can be recovered and reused several times without any significant loss of catalytic activity. A vanadium–Schiff base complex-functionalized SBA-15 was synthesized by covalency connected by a pre-synthesised VO2(picolinichydrazone) complex to silanated SBA-15. The synthesized vanadium–Schiff base complex was characterized by proton nuclear magnetic resonance (1H NMR) spectroscopy, carbon nuclear magnetic resonance (13C NMR) spectroscopy and Fourier transform infrared spectroscopy (FT-IR), and the final V/SBA-15 was characterized by FT-IR, ultraviolet–visible spectrophotometry and X-ray powder diffraction. The morphology of V/SBA-15 was also obtained by scanning electron microscopy and transmission electron microscopy. The catalytic effect was examined by using V/SBA-15 as a heterogeneous catalyst in sulfoxidation reactions. The synthesis of modafinil and modafinic acid by pharmaceutical sulfoxidation of solfides was carried out and the effects of different solvents, reaction times and also recoverability and reusability of the heterogeneous catalyst were investigated. This catalyst showed high yield of sulfide conversion, stability and recyclability in the sulfoxidation of sulfides.

Asymmetric Oxidation Synthesis of Modafinil Acid by Use of a Recyclable Chiral-at-Metal Complex

The enantioselective oxidation synthesis of chiral modafinil acid and its analogues with high enantiomeric excess has been developed by means of a chiral-at-metal strategy. Treatment of ruthenium complexes cis-[Ru(bpy)2Cl2] or Δ/Λ-[Ru(bpy)2(MeCN)2](PF6)2 (bpy is 2,2′-bipyridine) with the appropriate prochiral thioether ligands afforded thioether complexes rac-1, Δ/Λ-1, rac-2, Δ/Λ-2, rac-3, and Δ/Λ-3. Diastereoselective oxidation of the thioether complexes in situ produced the corresponding sulfoxide complexes rac-1a, Δ/Λ-1a, rac-2a, Δ/Λ-2a, rac-3a, and Δ/Λ-3a. The configuration at the metal center in each case is stable during the coordination and oxidation reactions, and dictates the chirality of the sulfoxide ligand in the oxidation process. The chiral modafinil acids were obtained with ee values greater than 98% upon their removal from the corresponding sulfoxide complexes in the presence of TFA/MeCN. Moreover, the chiral ruthenium precursors Δ/Λ-[Ru(bpy)2(MeCN)2](PF6)2 are recyclable and reusable with complete retention of the configurations. Chiral modafinil acid and its analogues have been synthesized with high ee values by means of asymmetric coordination oxidation of a thioether complex in situ with a chiral-at-metal strategy.

Simple synthesis of modafinil derivatives and their anti-inflammatory activity

Simple synthesis of modafinil derivatives and their biological activity are described. The key synthetic strategies involve substitution and coupling reactions. We determined the anti-inflammatory effects of modafinil derivatives in cultured BV2 cells by measuring the inhibition of nitrite production and expression of iNOS and COX-2 after LPS stimulation. It was found that for sulfide analogues introduction of aliphatic groups on the amide part (compounds 11a-d) resulted in lower anti-inflammatory activity compared with cyclic or aromatic moieties (compounds 11e-k). However, for the sulfoxide analogues, introduction of aliphatic moieties (compounds 12a-d) showed higher anti-inflammatory activity than cyclic or aromatic fragments (compounds 12e-k) in BV-2 microglia cells.

OXOPIPERAZINE DERIVATIVES FOR THE TREATMENT OF PAIN AND EPILEPSY

Compounds of formula (I) which are useful in ameliorating conditions characterized by unwanted sodium and/or calcium channel actrvrh, particularly Nav 1 7, NaV 1 8, or CaV 3 2 channel activity are disclosed. More specifica

PREPARATION OF ARMODAFINIL FORM I

Preparation of armodafinil crystalline Form I. Also provided is armodafinil having about 30% or more by weight of particles with sizes greater than about 250 μm, and about 70% or less by weight of particles having sizes less than about 250 μm, wherein of

Purification of armodafinil

The invention encompasses processes for obtaining pure armodafinil substantially free of disulfide impurities that is suitable for use on an industrial scale. In particular, a processes for purifying armodafinil from bis(diphenylmethyl)disulfide comprisin

PROCESS FOR THE PREPARATION OF MODAFINIL ENANTIOMERS

Disclosed herein is a convenient, commercially viable and environmentally friendly process for the preparation of Armodafinil. The present invention also provides an improved, commercially viable and industrially advantageous process for the preparation of pure 2-[(diphenylmethyl) sulfinyl] acetic acid (also known as modafinic acid) substantially free of sulfone impurity i.e., 2-[(diphenylmethyl)sulfonyl] acetic acid. The intermediate is useful for preparing Modafmil and its enantiomers, or a pharmaceutically acceptable salt thereof, in high yield and purity.

NOVEL CRYSTALLINE POLYMORPH OF ARMODAFINIL AND AN IMPROVED PROCESS FOR PREPARATION THEREOF

The present invention relates to a novel crystalline polymorph of armodafinil. In another aspect the invention relates to an improved process for preparation of the novel polymorph of armodafinil.