155690-08-7

Basic information

• Product Name: 2-p-Tolyl-3H,4H-2λ⁴-benzo[c][1,2]thiazine 2-oxide
• Synonyms: 2-p-Tolyl-3H,4H-2λ⁴-benzo[c][1,2]thiazine 2-oxide
• CAS NO: 155690-08-7
• Molecular Weight: 257.356
• Mol File: 155690-08-7.mol

Chemical Properties

• CAS DataBase Reference: 2-p-Tolyl-3H,4H-2λ⁴-benzo[c][1,2]thiazine 2-oxide(CAS DataBase Reference)
• NIST Chemistry Reference: 2-p-Tolyl-3H,4H-2λ⁴-benzo[c][1,2]thiazine 2-oxide(155690-08-7)
• EPA Substance Registry System: 2-p-Tolyl-3H,4H-2λ⁴-benzo[c][1,2]thiazine 2-oxide(155690-08-7)

Safety Data

• Hazardous Substances Data: 155690-08-7(Hazardous Substances Data)

Upstream product

• 123552-85-2 N-phenyl-S-(4-methylphenyl)sulfoximidoyl chloride 
• 754-05-2 ethenyltrimethylsilane 
• 6873-54-7 1-(p-tolylsulfinyl)aniline 

Downstream Products

• 578-54-1 ortho-ethylaniline 

Relevant articles and documents

The reaction of N-phenylsulfonimidoyl chloride with trimethylsilylethene. A new route to 2-alkenylanilines

N-Phenylsulfonimidoyl chloride reacts with trimethylsilylethene in the presence of aluminum chloride to give two product benzothiazines, one of which has been desilylated. The silylated benzothiazine can be deprotonated and alkylated, sometimes with very high diastereocontrol. Upon treatment with fluoride, these silylated benzothiazines undergo desilylation with concomitant cleavage of the carbon-sulfur bond to give 2- alkenylsulfinanilides which can be hydrolyzed to the corresponding anilines.

A general, regioselective approach to the synthesis of ortho allylanilines

Readily available 2,1-benzothiazines can be alkylated via deprotonation with butyllithium followed by treatment with iodomethyltrimethylsilane. Subsequent treatment with fluoride and hydrolysis leads to ortho allyl anilines in high yield. The reaction is general and regioselective by virtue of these characteristics being present in the Lewis acid mediated reaction of alkenes and sulfonimidoyl chlorides, the reaction which leads to the 2,1-benzothiazines used as starting materials.