2-methylbenzenesulfonyl azide

Base Information

• Chemical Name: 2-methylbenzenesulfonyl azide
• CAS No.: 13222-19-0
• Molecular Formula: C₇H₇N₃O₂S
• Molecular Weight: 197.217
• Mol file: 13222-19-0.mol

Synonyms:2-methylbenzenesulfonyl azide

Chemical Property of 2-methylbenzenesulfonyl azide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-methylbenzenesulfonyl azide

There total 3 articles about 2-methylbenzenesulfonyl azide 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: 80.0%

methyl 2-(aminosulfonyl)benzoate (88-19-7) → 2-methylbenzenesulfonyl azide (13222-19-0)

Guidance literature:

With 3-azidosulfonyl-3H-imidazole-1-ium hydrogen sulfate; potassium carbonate; In water; isopropyl alcohol; at 20 ℃; for 18h;

DOI:10.1021/jo500553q

Reference yield:

Toluene-2-sulfonyl chloride (133-59-5) → 2-methylbenzenesulfonyl azide (13222-19-0)

Guidance literature:

With sodium azide; In water; acetone; at 0 - 20 ℃; for 12h;

DOI:10.1016/j.cclet.2015.08.009

Reference yield:

→ 2-methylbenzenesulfonyl azide (13222-19-0)

Guidance literature:

entspr. Chlorid, NaN3;

DOI:10.1021/jo00898a042

upstream raw materials:

methyl 2-(aminosulfonyl)benzoate

Toluene-2-sulfonyl chloride

Downstream raw materials:

1-(m-tolyl)-2-(o-toluenesulfonylimino)indoline

2-methyl-N-(1-(2-methyl-1H-indol-3-yl)-2-oxo-2-phenylethylidene)benzenesulfonamide

(S,E)-(-)-N,N-dimethyl-2-oxo-2-phenyl-N'-(o-tolylsulfinyl)acetamidine

(E)-2-diazo-N,N-dimethyl-2-phenyl-N'-(o-tolylsulfonyl)acetamidine

Refernces

Ring expansion of substituted norbornadienes for the synthesis of mono- and disubstituted 2-azabicyclo[3.2.1]octadienes

10.1016/j.tetlet.2008.06.123

The study focuses on the synthesis of substituted 2-azabicyclo[3.2.1]octadienes, which are significant in the creation of natural products and biologically active compounds, through the ring expansion of substituted norbornadienes using toluenesulfonyl azide. The researchers explored the regioselectivity of the cycloaddition/rearrangement process with various mono- and disubstituted norbornadienes, finding that both types could be converted into the bicyclooctadiene ring system with high regiocontrol and in moderate to excellent yields. The study also investigated the impact of different substituent groups on the reaction's outcome, noting that electron-withdrawing groups resulted in little to no product, while hydroxymethyl derivatives provided a moderate yield of a single regioisomer. The synthesized 2-azabicyclo[3.2.1]octadienes can be further modified to yield highly substituted derivatives of the 2-azabicyclo[3.2.1]octane ring system, which is prevalent in natural products and pharmacologically active molecules, thus providing a valuable route for the synthesis of these complex structures.