212184-76-4

Basic information

• Product Name: N-(2-Benzenesulfinyl-ethyl)-N-(3-methoxy-benzyl)-formamide
• Synonyms: N-(2-Benzenesulfinyl-ethyl)-N-(3-methoxy-benzyl)-formamide
• CAS NO: 212184-76-4
• Molecular Weight: 317.409
• Mol File: 212184-76-4.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: N-(2-Benzenesulfinyl-ethyl)-N-(3-methoxy-benzyl)-formamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-(2-Benzenesulfinyl-ethyl)-N-(3-methoxy-benzyl)-formamide(212184-76-4)
• EPA Substance Registry System: N-(2-Benzenesulfinyl-ethyl)-N-(3-methoxy-benzyl)-formamide(212184-76-4)

Safety Data

• Hazardous Substances Data: 212184-76-4(Hazardous Substances Data)

Upstream product

• 212184-89-9 (3-Methoxy-benzyl)-(2-phenylsulfanyl-ethyl)-amine 
• 591-31-1 3-methoxy-benzaldehyde 
• 2014-75-7 2-(phenylthio)ethanamine 
• 212184-93-5 N-(3-Methoxy-benzyl)-N-(2-phenylsulfanyl-ethyl)-formamide 

Downstream Products

• 54893-23-1 7-methoxy-N-methyl-1,2,3,4-tetrahydroisoquinoline 
• 103030-70-2 5-methoxy-1,2,3,4-tetrahydro-isoquinoline 
• 43207-78-9 7-methoxy-1,2,3,4-tetrahydroisoquinoline 
• 212184-82-2 7-Methoxy-4-phenylsulfanyl-3,4-dihydro-1H-isoquinoline-2-carbaldehyde 
• 212184-83-3 5-Methoxy-4-phenylsulfanyl-3,4-dihydro-1H-isoquinoline-2-carbaldehyde 

Relevant articles and documents

A synthesis of mono- and dimethoxy-1,2,3,4-tetrahydroisoquinolines via Pummerer reaction: Effects of methoxyl groups on intramolecular cyclization

A synthesis of 1,2,3,4-tetrahydroisoquinolines (TIQs) (23) with one and two methoxyl groups at various positions of the benzene ring was achieved via the intramolecular cyclization of N-(aryl)methyl-2- (phenylsulfinyl)ethylamines (9) using the Pummerer reaction as a key step. The reaction was carried out by using trifluoroacetic anhydride (TFAA) (method A) or TFAA-BF3 · Et2O (method B). The cyclization to 4-SPhTIQs (11) proceeded effectively when the reaction center at the benzene ring was electronically activated by a methoxyl group. In the reaction of the sulfoxide (9e) having two OMe groups at ortho- and para-positions a different cyclization reaction leading to a benzothiazepine (12) was observed, indicating that the high nucleophilicity of the benzene ring caused the unexpected reaction prior to the cyclization to 4-SPhTIQ (11e). The route starting from methoxylated benzaldehydes (5) was proved to provide an efficient and convenient method of TIQ synthesis which should be complementary to the well known Pictet-Spengler method.