cis-2-(2,4-Dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-ylmethyl toluene-p-sulphonate

Base Information

• Chemical Name: cis-2-(2,4-Dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-ylmethyl toluene-p-sulphonate
• CAS No.: 134071-44-6
• Molecular Formula: C₂₁H₂₀Cl₂N₂O₅S
• Molecular Weight: 483.372
• European Community (EC) Number: 288-058-5,603-791-6
• DSSTox Substance ID: DTXSID40234903
• Nikkaji Number: J1.290.348K
• Mol file: 134071-44-6.mol

Synonyms:85650-50-6;cis-2-(2,4-Dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-ylmethyl toluene-p-sulphonate;EINECS 288-058-5;[(2S,4S)-2-(2,4-dichlorophenyl)-2-(imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methyl 4-methylbenzenesulfonate;SCHEMBL6315562;DTXSID40234903;WAXNIYHZFWRPGS-LAUBAEHRSA-N;(cis-2-((1H-Imidazol-1-yl)methyl)-2-(2,4-dichlorophenyl)-1,3-dioxolan-4-yl)methyl 4-methylbenzenesulfonate;134071-44-6;((2s,4s)-2-((1h-imidazol-1-yl)methyl)-2-(2,4-dichlorophenyl)-1,3-dioxolan-4-yl)methyl 4-methylbenzenesulfonate

Chemical Property of cis-2-(2,4-Dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-ylmethyl toluene-p-sulphonate

Chemical Property:

• Appearance/Colour: Off-white solid
• Vapor Pressure: 3.58E-17mmHg at 25°C
• Melting Point: 120-122 °C
• Refractive Index: 1.65
• Boiling Point: 665.674 °C at 760 mmHg
• PKA: 6.88±0.12(Predicted)
• Flash Point: 356.387 °C
• PSA: 88.03000
• Density: 1.444 g/cm³
• LogP: 5.25300
• Storage Temp.: -20°C Freezer
• XLogP3: 4.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 7
• Exact Mass: 482.0469983
• Heavy Atom Count: 31
• Complexity: 700

Purity/Quality:

99% ^*data from raw suppliers

cis-[2-(2,4-Dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methylp-Tolylsulfonate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC=C(C=C1)S(=O)(=O)OCC2COC(O2)(CN3C=CN=C3)C4=C(C=C(C=C4)Cl)Cl
• Isomeric SMILES: CC1=CC=C(C=C1)S(=O)(=O)OC[C@@H]2CO[C@@](O2)(CN3C=CN=C3)C4=C(C=C(C=C4)Cl)Cl
• Uses: An intermediate in the synthesis of the drug Ketoconazole (K186000). cis-[2-(2,4-Dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methyl p-Tolylsulfonate (Ketoconazole EP Impurity E) is an intermediate in the synthesis of the drug Ketoconazole (K186000).

Technology Process of cis-2-(2,4-Dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-ylmethyl toluene-p-sulphonate

There total 25 articles about cis-2-(2,4-Dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-ylmethyl toluene-p-sulphonate 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: 89.0%

p-toluenesulfonyl chloride (98-59-9) + [2-(2,4-dichloro-phenyl)-2-imidazol-1-ylmethyl-[1,3]dioxolan-4-yl]-methanol (84682-23-5) → Toluene-4-sulfonic acid 2-(2,4-dichloro-phenyl)-2-imidazol-1-ylmethyl-[1,3]dioxolan-4-ylmethyl ester (134071-44-6)

Guidance literature:

With pyridine; 1.) 0 deg C, 1 h, 2.) RT, 48 h;

DOI:10.1016/0223-5234(96)88277-8

Reference yield: 80.0%

cis-2-(2,4-Dichlorophenyl)-2-[(1H-imidazol-1-yl)methyl]-1,3-dioxolane-4-methanol (61397-58-8,61441-65-4,68684-88-8,68685-07-4,84682-23-5) + p-toluenesulfonyl chloride (98-59-9) → cis-2-(2,4-dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-ylmethyl toluene-p-sulphonate (85650-50-6,134071-44-6)

Guidance literature:

In pyridine; 1) ice-cold, 1 h, 2) RT, 18 h;

Reference yield: 13.0%

(S)-3-tosyl-1,2-propanediol + 1-(2,4-dichlorophenyl)-2-(imidazol-1-yl)ethanone (46503-52-0) → ((2S,4S)-2-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)methyl-1,3-dioxolan-4-yl)methyl 4-methylbenzenesulfonate (134071-44-6) + ((2R,4S)-2-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)methyl-1,3-dioxolan-4-yl)methyl 4-methylbenzenesulfonate (134071-44-6)

Guidance literature:

With toluene-4-sulfonic acid; In toluene; for 12h; Dean-Stark; Reflux;

DOI:10.1016/j.bmcl.2019.126794

upstream raw materials:

cis-2-(2,4-Dichlorophenyl)-2-[(1H-imidazol-1-yl)methyl]-1,3-dioxolane-4-methanol

p-toluenesulfonyl chloride

2-(2,4-dichlorophenyl)-2-bromomethyl-4-hydroxymethyl-1,3-dioxolane

(2-(2,4-dichlorophenyl)-2-methyl-1,3-dioxolan-4-yl)methanol

Refernces

• 1、 Cheng, Zhiqiang,Head, Sarah A.,Li, Ruo-Jing,Li, Yingjun,Liu, Jun O.,Liu, Wukun,Pasunooti, Kalyan Kumar,Peng, Hanjing,Shi, Wei Q.. "Design and Synthesis of Tetrazole- And Pyridine-Containing Itraconazole Analogs as Potent Angiogenesis Inhibitors". . p. 1111 - 1117. Retrieved 2020/07/04.
• 2、 Power, Eoin C.,Ganellin, C. Robin,Benton, David C.H.. "Partial structures of ketoconazole as modulators of the large conductance calcium-activated potassium channel (BKCa)". . p. 887 - 890. Retrieved 2007/10/03.