29690-20-8

Upstream product

• 75-18-3 dimethylsulfide 
• 2101-86-2 p-methylazidobenzene 
• 624-92-0 Dimethyldisulphide 
• 106-49-0 p-toluidine 
• 2536-91-6 6-methylbenzothiazol-2-ylamine 
• 446-34-4 2-fluoro-4-methyl-1-nitrobenzene 

Downstream Products

• 30322-02-2 7-methyl, 2H-1,4-benzothiazin-3(4H)-one 
• 882423-17-8 N-(4-aminomethyl-2-methanesulfonyl-phenyl)-methanesulfonamide 
• 866005-26-7 (2-methanesulfonyl-4-methyl-phenyl)-carbamic acid tert-butyl ester 
• 866005-34-7 N-(4-azidomethyl-2-methanesulfonyl-phenyl)-methanesulfonamide 
• 882420-28-2 (4-bromomethyl-2-methanesulfonyl-phenyl)-carbamic acid tert-butyl ester 
• 866005-30-3 (4-azidomethyl-2-methanesulfonyl-phenyl)-carbamic acid tert-butyl ester 
• 27047-29-6 6-methyl-2-phenylbenzothiophen 
• 10205-58-0 6-methyl-2-phenyl-1,3-benzothiazole 

Relevant academic research and scientific papers

Ionic Reactivity of 2-Isocyanoaryl Thioethers: Access to 2-Halo and 2-Aminobenzothia/Selenazoles

An ionic cascade insertion/cyclization reaction of thia-/selena-functionalized arylisocyanides has been successfully developed for the efficient and practical synthesis of 2-halobenzothiazole/benzoselenazole derivatives. This synthetic protocol, incorporating a halogen atom when forming the five-membered ring of benzothia/selenazoles, is different from the existing ones, where halogenation of the preformed benzothia/selenazole precursors happens. Additionally, a facile access to 2-aminobenzothiazoles is also achieved by the one-pot cascade reaction of 2-isocyanoaryl thioethers, iodine, and amines.

Facile syntheses of 3-trifluoromethylthio substituted thioflavones and benzothiophenes via the radical cyclization

3-CF3S substituted thioflavones and benzothiophenes were achieved via the reactions of AgSCF3 with methylthiolated alkynones and alkynylthioanisoles, respectively, promoted by persulfate. This protocol possesses good functional group tolerance and high yields. Mechanistic studies suggested that a classic two-step radical process was involved, which includes addition of CF3S radical to triple bond and cyclization with SMe moiety.

Visible light photocatalytic synthesis of benzothiophenes

The photocatalytic reaction of o-methylthio-arenediazonium salts with alkynes yields substituted benzothiophenes regioselectively through a radical annulation process. Green light irradiation of eosin Y initiates the photoredox catalysis. The scope of the reaction was investigated by using various substituted diazonium salts and different alkynes.

Process for preparing (hydrocarbylthio) aromatic amines

(Hydrocarbylthio)aromatic amines are prepared by reacting an aromatic amine, such as an aminobenzene, with a hydrocarbyl disulfide, such as an alkyl disulfide, in the presence of iodine, iodine monochloride, or iodine monobromide as a catalyst.

Formation of Sommelet-Hauser-Type Products, 2-Aminoarylmethyl Sulphides, and Nitrenium Ion Products, 2- and 4-Aminoaryl Sulphides, via an N-Arylazasulphonium Salt

Reactions of a salt (1) formed at -60 deg C from trifluoroacetic anhydride and dimethyl sulphoxide (DMSO) with primary and secondary arylamines gave 2-aminoarylmethyl sulphides (6), (6') and (12) by a Sommelet-Hauser rearrangement of an ylide (5) formed by loss of a methyl proton of an N-arylazasulphonium salt (3) in the absence of base.The use of ethyl methyl sulphoxide instead of DMSO afforded a similar product (19b) by loss of not the ethyl but the methyl proton.However, the use of diethyl sulphoxide merely caused loss of an ethyl group from the N-arylazasulphonium salt to yield ethanesulphenanilide (20).The reaction of (1) with N-phenyl-1-naphthylamine gave mainly aminoaryl sulphides (13) and (14) via an arylnitrenium ion from the N-arylazasulphonium salt.In fact, the reaction of dimethyl sulphide (DMS) with arylnitrenium ions formed in the acid decomposition of aryl azides gave no Sommelet-Hauser-type products but 2- and 4-aminoaryl sulphides (22), (22') and (23).We also discuss the possibility of the N-arylazasulphonium salt being formed by reaction of the arylnitrenium ion with DMS.

Poly(hydrocarbylthio)anilines

Novel poly(hydrocarbylthio)anilines are 2,4,6-trisubstituted anilines wherein the substituents in at least two of the ortho and para positions are hydrocarbylthio substituents, any other p-substituent is hydrocarbyl or hydrocarbyloxy, any other ar-substituents are chloro, fluoro, hydrocarbyl, hydrocarbyloxy, and/or hydrocarbylthio, and any N-substituents are hydrocarbyl.

Process for preparing (hydrocarbylthio)aromatic amines

(Hydrocarbylthio)aromatic amines are prepared by reacting an aromatic amine, such as an aminobenzene, with a hydrocarbyl disulfide, such as an alkyl disulfide. The reaction is preferably conducted in the presence of a Lewis acid catalyst, such as aluminum chloride.