N,N-Dimethyl-4-[(4-methylbenzene-1-sulfonyl)methyl]aniline

Base Information

• Chemical Name: N,N-Dimethyl-4-[(4-methylbenzene-1-sulfonyl)methyl]aniline
• CAS No.: 33933-62-9
• Molecular Formula: C16H19NO2S
• Molecular Weight: 289.398
• DSSTox Substance ID: DTXSID00601874
• Wikidata: Q82498731
• Mol file: 33933-62-9.mol

Synonyms:33933-62-9;N,N-Dimethyl-4-[(4-methylbenzene-1-sulfonyl)methyl]aniline;N,N-dimethyl-4-[(4-methylphenyl)sulfonylmethyl]aniline;DTXSID00601874

Chemical Property of N,N-Dimethyl-4-[(4-methylbenzene-1-sulfonyl)methyl]aniline

Chemical Property:

• XLogP3: 2.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 289.11365002
• Heavy Atom Count: 20
• Complexity: 383

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC=C(C=C1)S(=O)(=O)CC2=CC=C(C=C2)N(C)C

Technology Process of N,N-Dimethyl-4-[(4-methylbenzene-1-sulfonyl)methyl]aniline

There total 8 articles about N,N-Dimethyl-4-[(4-methylbenzene-1-sulfonyl)methyl]aniline which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 93.0%

4-bromo-N,N-dimethylaniline (586-77-6) + Methyl p-tolyl sulfone (3185-99-7) → N,N-dimethyl-4-[(4-methylbenzenesulfonyl)methyl]aniline (33933-62-9)

Guidance literature:

4-bromo-N,N-dimethylaniline; Methyl p-tolyl sulfone; With bis(dibenzylideneacetone)-palladium⁽⁰⁾; XPhos; In tetrahydrofuran; at 20 ℃; for 0.166667h; Inert atmosphere; Sealed tube;

With C₉H₁₉N*LiCl*ZnCl₂; In tetrahydrofuran; at 60 ℃; for 16h; Inert atmosphere; Sealed tube;

DOI:10.1021/acs.joc.6b01062

Reference yield: 82.0%

p-(dimethylamino)benzaldehyde tosylhydrazone (18708-16-2) → N,N-dimethyl-4-[(4-methylbenzenesulfonyl)methyl]aniline (33933-62-9)

Guidance literature:

With iron(III)phthalocyanine chloride; potassium carbonate; In 1,4-dioxane; at 80 ℃; for 3h;

DOI:10.1016/j.tetlet.2016.04.044

Reference yield: 71.0%

[(p-methylphenyl)sulfonylmethyl]isonitrile (38622-91-2,36635-61-7) + N,N-dimethyl-aniline (121-69-7,77733-26-7) → N,N-dimethyl-4-[(4-methylbenzenesulfonyl)methyl]aniline (33933-62-9)

Guidance literature:

With iron(II) chloride tetrahydrate; In water; at 100 ℃; for 10h; regioselective reaction; Sealed tube; Inert atmosphere;

DOI:10.1021/acs.joc.1c00500

upstream raw materials:

p-toluene sulfinic acid

N,N-dimethyl-aniline

p-(dimethylamino)benzaldehyde tosylhydrazone

4-dimethylamino-benzaldehyde