118286-24-1

Upstream product

• 954-67-6 benzhydryl acetate 
• 2365-48-2 Methyl thioglycolate 
• 776-74-9 Bromodiphenylmethane 
• 91-01-0 1,1-Diphenylmethanol 
• 865811-65-0 (S)-(+)-methyl (diphenylmethanesulfinyl)-acetate 
• 100865-93-8 O-diphenylmethyl 2,2,2-trichloroacetimidate 
• 101-81-5 Diphenylmethane 
• 63547-22-8 (benzhydrylthio)acetic acid 
• 74-88-4 methyl iodide 
• 90280-15-2 diphenylmethylisothiouronium bromide 
• 96-34-4 methyl chloroacetate 

Downstream Products

• 68524-30-1 2-(diphenylmethylthio)acetamide 
• 112111-43-0 Nuvigil 
• 112111-43-0 Modafinil 
• 713134-72-6 (R)-(-)-methyl (diphenylmethanesulfinyl)-acetate 
• 865811-65-0 (S)-(+)-methyl (diphenylmethanesulfinyl)-acetate 

Relevant academic research and scientific papers

Towards a robust and reliable method for the reduction of functionalized sulfoxides

Several functionalized sulfoxides in the modafinil series, which bear another reducible function, were chemoselectively reduced to thioethers using the KI/AcCl system.

Nickel-catalyzed oxidative dehydrogenative coupling of alkane with thiol for C(sp3)-S bond formation

A nickel-catalyzed oxidative dehydrogenative coupling reaction of alkane with thiol for the construction of C(sp3)-S bond has been established, affording more than 50 alkyl thioethers. Notably, pharmaceutical and agrochemicals, such as Provigil, Chlorbenside and Pyridaben, were readily synthesized by this approach. The sterically hindered ligand BC and disulfide which was formed in situ oxidation of thiol, efficiently avoiding nickel-catalyst poisoning. A set of mechanistic experiments disclose both Ni-catalyzed and Ni-free HAA processes.

Efficient atom and step economic (EASE) synthesis of the "smart drug" Modafinil

Modafinil (2-[(diphenylmethyl)sulfinyl]acetamide, MOD) is a key psychostimulant drug used for the treatment of narcolepsy and other sleep disorders that has a very low addiction liability. Recently, MOD has been clinically investigated for the treatment of cocaine addiction and used by astronauts in long-term space missions. We have developed a synthetic strategy for "smart drug" Modafinil. An efficient atom and step economic (EASE) synthesis has been carried out by the direct reaction of benzhydrol and 2-mercaptoacetamide using the recyclable heterogeneous catalyst Nafion-H along with post-sulfoxidation. This protocol exhibits improved sustainability credentials. We have also developed a superior pre-sulfoxidation approach for the synthesis of Modafinil.

ION PAIR CATALYSIS OF TUNGSTATE AND MOLYBDATE

D The present invention relates to ion pair catalysts (I) comprising the cationic bisguanidinium ligand (A) and diperoxomolybdate anion (B). The present invention also relates to ion pair catalysts (III) comprising the cationic bisguanidinium ligand (C) and peroxotungstate anion (D). It further relates to the use of the said catalysts in the manufacture of enantiomerically enriched sulfoxides.

Alkylation of thiols with trichloroacetimidates under neutral conditions

Trichloroacetimidates are displaced with thiols to form the corresponding sulfides without the need for an added acid or base by simply heating the reactants in refluxing THF. This operationally simple procedure provides the corresponding sulfides in excellent yields with only the formation of the neutral trichloroacetamide as the side product. The imidate may also be formed in situ, allowing for a direct method for the formation of sulfides from alcohols. This reaction provides a general method for the synthesis of a variety of sulfides from inexpensive and readily available alcohol starting materials.

Protic ionic liquids as recyclable solvents for the acid catalysed synthesis of diphenylmethyl thioethers

The acid catalysed formation of diphenylmethyl (DPM) thioethers was successfully achieved using the protic ionic liquid (pIL) triethylamine: methanesulfonic acid (TeaMs) as the reaction solvent under microwave irradiation. A slight excess of methanesulfon

SARs at the monoamine transporters for a novel series of modafinil analogues

A series of modafinil (1) analogues were synthesized wherein (1) para-halo-substitutents were added to the aryl rings, (2) the sulfoxide function was removed, and (3) the primary amide group was replaced with secondary and tertiary amides and amines to investigate the effects of these chemical modifications on dopamine transporter, serotonin transporter, and norepinephrine transporter binding. In addition, the locomotor-stimulant effects in mice of (±)-modafinil (1), its R-and S-enantiomers, and its para-chloro sulfinylacetamide analogue (5c) were compared to those of cocaine.

IMPROVED PROCESS FOR PREPARING BENZHYDRYLTHIOACETAMIDE

The present invention is directed to an improved process for preparing modafinil wherein benzhydrylthioacetate is prepared in high yield and purity by the reaction of a haloacetate with the reaction product of thiourea and benzhydrol. The reaction employing the haloacetate is conducted in a solvent comprising an organic solvent such as methanol having dissolved therein an organic base or an inorganic basic salt such as sodium bicarbonate. The resulting benzhydrylthioacetate can be amidated and then oxidized to provide the pharmaceutical grade modafinil in high yield and purity.

Novel method for preparing methyl 2-diphenylmethylsulfinylacetate

Method for preparing methyl 2-diphenylmethylsulfinylacetate (MDMSA) comprising the steps of :(i) conversion of benzhydrol into methyldiphenylmethylthioacetate ; and(ii) conversion of methyldiphenylmethylthioacetate into methyl-2-diphenylmethylsulfinylacet

Method of selectively inhibiting prostaglandin G/H synthase-2

The present invention provides a method of selectively inhibiting prostaglandin G/H synthase-2 that comprises administering to a patient in need of such inhibition an inhibiting amount of a compound having the Formula I, II or III STR1 wherein the R group