4-methyl-N'-[(E,2E)-1-methyl-3-phenyl-2-propenylidene]benzenesulfonohydrazide

Base Information

• Chemical Name: 4-methyl-N'-[(E,2E)-1-methyl-3-phenyl-2-propenylidene]benzenesulfonohydrazide
• CAS No.: 17336-65-1
• Molecular Formula: C17H18 N2 O2 S
• Molecular Weight: 314.408
• NSC Number: 333418
• DSSTox Substance ID: DTXSID40430660
• Mol file: 17336-65-1.mol

Synonyms:NSC333418;17336-65-1;DTXSID40430660;AKOS024344428;NSC-333418;4-methyl-N'-[(E,2E)-1-methyl-3-phenyl-2-propenylidene]benzenesulfonohydrazide

Chemical Property of 4-methyl-N'-[(E,2E)-1-methyl-3-phenyl-2-propenylidene]benzenesulfonohydrazide

Chemical Property:

• XLogP3: 3.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 314.10889899
• Heavy Atom Count: 22
• Complexity: 491

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of 4-methyl-N'-[(E,2E)-1-methyl-3-phenyl-2-propenylidene]benzenesulfonohydrazide

There total 4 articles about 4-methyl-N'-[(E,2E)-1-methyl-3-phenyl-2-propenylidene]benzenesulfonohydrazide 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:

toluene-4-sulfonic acid hydrazide (1576-35-8) + 1-Phenylbut-1-en-3-one (122-57-6) → 4-phenylbut-3-en-2-one p-tosylhydrazone (17336-65-1)

Guidance literature:

With hydrogenchloride; In methanol;

DOI:10.1246/bcsj.44.1885

Reference yield:

benzaldehyde (100-52-7) → 4-phenylbut-3-en-2-one p-tosylhydrazone (17336-65-1)

Guidance literature:

Multi-step reaction with 2 steps

1: ethanol; water / 0.08 h / 20 °C / Inert atmosphere

2: methanol / 60 °C / Inert atmosphere

In methanol; ethanol; water;

DOI:10.1021/acs.orglett.7b00213

Reference yield:

bromobenzene (108-86-1,52753-63-6) → 4-phenylbut-3-en-2-one p-tosylhydrazone (17336-65-1)

Guidance literature:

Multi-step reaction with 2 steps

1: tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; tetrabutyl-ammonium chloride; sodium hydrogencarbonate / N,N-dimethyl-formamide / 4 h / 100 °C / Microwave irradiation; Inert atmosphere

2: sulfuric acid / 1.5 h / 80 °C / Microwave irradiation

With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; sulfuric acid; tetrabutyl-ammonium chloride; sodium hydrogencarbonate; In N,N-dimethyl-formamide; 1: |Heck Reaction;

DOI:10.1002/ejoc.202000066

upstream raw materials:

toluene-4-sulfonic acid hydrazide

1-Phenylbut-1-en-3-one

(E)-benzalacetone

benzaldehyde

Downstream raw materials:

p-toluenesulfonyl chloride

4-((E)-Styryl)-[1,2,3]thiadiazole

5-(α-chlorobenzyl)-4-methyl-1,2,3-thiadiazole

1-Phenylbut-1-en-3-one

Refernces

• 1、 Zeng, Lin,Guo, Xiao-Qiang,Yang, Zai-Jun,Gan, Ya,Chen, Lian-Mei,Kang, Tai-Ran. "Metal-free and highly regioselective synthesis of N-heteroaryl substituted pyrazoles from α,β-unsaturated N-tosylhydrazones and heteroaryl chlorides". supporting information. . Retrieved 2019/07/30.
• 2、 Wang, Ting-Ting,Wang, Fu-Xiang,Yang, Fu-Lai,Tian, Shi-Kai. "Palladium-catalyzed aerobic oxidative coupling of enantioenriched primary allylic amines with sulfonyl hydrazides leading to optically active allylic sulfones". supporting information. p. 3802 - 3805. Retrieved 2014/04/03.