4-methyl-N-[(E)-(2,2,5,5-tetramethyl-3-oxocyclohexylidene)amino]benzenesulfonamide

Base Information

• Chemical Name: 4-methyl-N-[(E)-(2,2,5,5-tetramethyl-3-oxocyclohexylidene)amino]benzenesulfonamide
• CAS No.: 15500-76-2
• Molecular Formula: C17H24 N2 O3 S
• Molecular Weight: 336.455
• DSSTox Substance ID: DTXSID40422080
• Mol file: 15500-76-2.mol

Synonyms:MLS003106914;DTXSID40422080;15500-76-2

Chemical Property of 4-methyl-N-[(E)-(2,2,5,5-tetramethyl-3-oxocyclohexylidene)amino]benzenesulfonamide

Chemical Property:

• Boiling Point: 467.2°Cat760mmHg
• Flash Point: 236.4°C
• Density: 1.19g/cm³
• XLogP3: 3.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 3
• Exact Mass: 336.15076381
• Heavy Atom Count: 23
• Complexity: 592

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)NN=C2CC(CC(=O)C2(C)C)(C)C
• Isomeric SMILES: CC1=CC=C(C=C1)S(=O)(=O)N/N=C/2\CC(CC(=O)C2(C)C)(C)C

Technology Process of 4-methyl-N-[(E)-(2,2,5,5-tetramethyl-3-oxocyclohexylidene)amino]benzenesulfonamide

There total 2 articles about 4-methyl-N-[(E)-(2,2,5,5-tetramethyl-3-oxocyclohexylidene)amino]benzenesulfonamide 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:

2,2,5,5-tetramethylcyclohexa-1,3-dione (702-50-1) + toluene-4-sulfonic acid hydrazide (1576-35-8) → Dimethyl-dimedon-mono-(toluol-4-sulfonyl-hydrazon) (15500-76-2)

Guidance literature:

In ethanol; at 20 ℃; for 168h; Inert atmosphere;

DOI:10.1002/hlca.201200393

Reference yield:

→ Dimethyl-dimedon-mono-(toluol-4-sulfonyl-hydrazon) (15500-76-2)

Guidance literature:

Dimethyl-dimedon, Toluol-4-sulfonyl-hydrazin (neben Dimethyl-dimedon-bis- (1c));

DOI:10.1021/jo01349a076

Reference yield:

Dimethyl-dimedon-mono-(toluol-4-sulfonyl-hydrazon) (15500-76-2) → trans-chrysanthemic acid (827-90-7,2259-14-5,2935-23-1,4638-92-0,10453-89-1,15259-78-6,26771-06-2,26771-11-9,705-16-8) + cis-Chrysanthemic acid (2935-23-1)

Guidance literature:

Multi-step reaction with 4 steps

1.1: ethylene glycol; sodium / 180 °C / Inert atmosphere

2.1: 3-chloro-benzenecarboperoxoic acid; sodium hydrogencarbonate / dichloromethane / 40 h / 20 °C / Inert atmosphere

3.1: titanium(IV) bromide / dichloromethane / 72 h / 20 °C / Inert atmosphere

3.2: 5.5 h / -10 - 20 °C / Inert atmosphere

4.1: potassium tert-butylate / water; dimethyl sulfoxide / 2 h / 20 °C / Inert atmosphere

4.2: pH 2 / Cooling with ice

With potassium tert-butylate; sodium; titanium(IV) bromide; sodium hydrogencarbonate; ethylene glycol; 3-chloro-benzenecarboperoxoic acid; In dichloromethane; water; dimethyl sulfoxide;

DOI:10.1002/hlca.201200393

upstream raw materials:

2,2,5,5-tetramethylcyclohexa-1,3-dione

toluene-4-sulfonic acid hydrazide

Downstream raw materials:

2,2,5,5-tetramethylcyclohex-3-en-1-one

C₁₀H₁₇ClO₂

(3S,4S)-4-chloro-3-hydroxy-2,2,5,5-tetramethylcyclohexanone

(1S)-(3R,4R)-3,4-dibromo-2,2,5,5-tetramethylcyclohexanol