N-(3-cyclopropylprop-2-yn-1-yl)-4-methylbenzenesulfonamide

Base Information

• Chemical Name: N-(3-cyclopropylprop-2-yn-1-yl)-4-methylbenzenesulfonamide
• CAS No.: 1401797-88-3
• Molecular Formula: C₁₃H₁₅NO₂S
• Molecular Weight: 249.334
• Mol file: 1401797-88-3.mol

Synonyms:N-(3-cyclopropylprop-2-yn-1-yl)-4-methylbenzenesulfonamide

Chemical Property of N-(3-cyclopropylprop-2-yn-1-yl)-4-methylbenzenesulfonamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-(3-cyclopropylprop-2-yn-1-yl)-4-methylbenzenesulfonamide

There total 5 articles about N-(3-cyclopropylprop-2-yn-1-yl)-4-methylbenzenesulfonamide 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: 71.0%

tert-butyl (3-cyclopropylprop-2-yn-1-yl)(tosyl)carbamate (1428676-48-5) → N-(3-cyclopropylprop-2-yn-1-yl)-4-methylbenzenesulfonamide (1401797-88-3)

Guidance literature:

tert-butyl (3-cyclopropylprop-2-yn-1-yl)(tosyl)carbamate; With methanol; lithium hydroxide; In tetrahydrofuran; at 20 ℃; for 12h; Inert atmosphere;

With hydrogenchloride; water; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1021/jo4002432

Reference yield:

cyclopropyliodide (19451-11-7) + 4-methyl-N-prop-2-ynylbenzenesulfonamide (55022-46-3) → N-(3-cyclopropylprop-2-yn-1-yl)-4-methylbenzenesulfonamide (1401797-88-3)

Guidance literature:

With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; In N,N-dimethyl-formamide; at 50 ℃; for 19h; Inert atmosphere;

DOI:10.1002/chem.201806083

Reference yield:

N-[(tert-butoxy)carbonyl]-4-methylbenzenesulfonamide (18303-04-3) → N-(3-cyclopropylprop-2-yn-1-yl)-4-methylbenzenesulfonamide (1401797-88-3)

Guidance literature:

Multi-step reaction with 2 steps

1: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 11 h / 0 °C / Inert atmosphere

2: lithium hydroxide; methanol / tetrahydrofuran / 12 h / 20 °C / Inert atmosphere

With methanol; di-isopropyl azodicarboxylate; triphenylphosphine; lithium hydroxide; In tetrahydrofuran; 1: |Mitsunobu Displacement;

DOI:10.1021/jo4002432

upstream raw materials:

3-cyclopropylprop-2-yn-1-ol

N-[(tert-butoxy)carbonyl]-4-methylbenzenesulfonamide

tert-butyl (3-cyclopropylprop-2-yn-1-yl)(tosyl)carbamate

p-toluenesulfonyl chloride

Downstream raw materials:

(S)-8-cyclopropyl-5-[dimethyl(phenyl)silyl]-6-methyl-2-tosyl-1,2,3,4-tetrahydrocyclopenta[c]azepin-7(6H)-one

(E )-N-(3-(4-methoxyphenyl)allyl)-4-methyl-N-(pent-2-ynyl)benzenesulfonamide

Refernces

• 1、 Grillet, Francois,Brummond, Kay M.. "Enantioselective synthesis of 5,7-bicyclic ring systems from axially chiral allenes using a Rh(I)-catalyzed cyclocarbonylation reaction". . p. 3737 - 3754. Retrieved 2013/06/04.