Neticonazole hydrochloride

Base Information

• Chemical Name: Neticonazole hydrochloride
• CAS No.: 130773-02-3
• Molecular Formula: C17H22 N2 O S . Cl H
• Molecular Weight: 338.901
• UNII: PKF582ZH6P
• Wikidata: Q27286599
• Mol file: 130773-02-3.mol

Synonyms:1-(2-(methylthio)-1-(2-(pentyloxy)phenyl)ethenyl)-1H-imidazole;neticonazole;SS-717;SS717

Chemical Property of Neticonazole hydrochloride

Chemical Property:

• Vapor Pressure: 8.66E-09mmHg at 25°C
• Melting Point: 145-147°
• Boiling Point: 464°Cat760mmHg
• Flash Point: 234.4°C
• PSA: 52.35000
• Density: 1.06g/cm³
• LogP: 5.46380
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 8
• Exact Mass: 338.1219622
• Heavy Atom Count: 22
• Complexity: 322

Purity/Quality:

98%Min ^*data from raw suppliers

Neticonazole(hydrochloride) 98.58% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Moderately toxic by ingestion.
• Hazard Codes: Moderately toxic by ingestion.

MSDS Files:

Useful:

• Canonical SMILES: CCCCCOC1=CC=CC=C1C(=CSC)N2C=CN=C2.Cl
• Isomeric SMILES: CCCCCOC1=CC=CC=C1/C(=C\SC)/N2C=CN=C2.Cl
• Description: Neticonazole hydrochloride is a novel imidazole antifungal agent introduced for the treatment of infections caused by Candida species. One percent neticonazole cream oncedaily application has been reported to be effective in treating patients with tinea pedis, tinea corporis, tinea cruris, intertrigo-type candidiasis, erosio interdigitalis and tinea versicolor. Compared with other agents of the azole class, neticonazole has the most potent activity against a variety of fungi, including the dermatophytes and pathogenic yeasts. It also has activity against Gram-positive, but not Gram-negative bacteria.

Technology Process of Neticonazole hydrochloride

There total 4 articles about Neticonazole hydrochloride 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: 73.2%

amyl iodide (628-17-1) + (E)-1-<1-(2-Hydroxyphenyl)-2-(methylthio)ethenyl>-1H-imidazole (138206-46-9) → (E)-1-[2-methylthio-1-[2-(pentyloxy)phenyl]ethenyl]-1H-imidazole hydrochloride (130773-02-3)

Guidance literature:

amyl iodide; (E)-1-<1-(2-Hydroxyphenyl)-2-(methylthio)ethenyl>-1H-imidazole; With potassium hydroxide; In N,N-dimethyl-formamide; at 20 ℃; for 3.5h;

With hydrogenchloride; In water; ethyl acetate; for 10h;

Reference yield: 72.7%

1-Bromopentane (110-53-2) + (E)-1-<1-(2-Hydroxyphenyl)-2-(methylthio)ethenyl>-1H-imidazole (138206-46-9) → (E)-1-[2-methylthio-1-[2-(pentyloxy)phenyl]ethenyl]-1H-imidazole hydrochloride (130773-02-3)

Guidance literature:

1-Bromopentane; (E)-1-<1-(2-Hydroxyphenyl)-2-(methylthio)ethenyl>-1H-imidazole; With potassium hydroxide; In N,N-dimethyl-formamide; at 20 ℃; for 3.5h;

With hydrogenchloride; In water; ethyl acetate; for 10h; Reagent/catalyst;

Reference yield:

salicylic acid (69-72-7,25496-36-0,8052-31-1) → (E)-1-[2-methylthio-1-[2-(pentyloxy)phenyl]ethenyl]-1H-imidazole hydrochloride (130773-02-3)

Guidance literature:

Multi-step reaction with 3 steps

1.1: benzotriazol-1-ol; dicyclohexyl-carbodiimide / N,N-dimethyl-formamide / 1 h / 25 - 30 °C

1.2: 4 h / 25 - 30 °C

2.1: triphenylphosphine; triethylamine / N,N-dimethyl-formamide / 1 h / 20 °C

2.2: 3 h / 90 - 100 °C

3.1: potassium hydroxide / N,N-dimethyl-formamide / 3.5 h / 20 °C

3.2: 10 h

With benzotriazol-1-ol; triethylamine; dicyclohexyl-carbodiimide; triphenylphosphine; potassium hydroxide; In N,N-dimethyl-formamide; 2.1: |Wittig Rearrangement / 2.2: |Wittig Rearrangement;

upstream raw materials:

amyl iodide

(E)-1-<1-(2-Hydroxyphenyl)-2-(methylthio)ethenyl>-1H-imidazole

1-Bromopentane

1-(1-(2-hydroxyphenyl)-2-methanone)-1H-imidazole