Methyl 2-(1-tosyl-1H-imidazol-4-YL)acetate

Base Information

• Chemical Name: Methyl 2-(1-tosyl-1H-imidazol-4-YL)acetate
• CAS No.: 497159-97-4
• Molecular Formula: C13H14N2O4S
• Molecular Weight: 294.33
• DSSTox Substance ID: DTXSID60463137
• Wikidata: Q82287928
• Mol file: 497159-97-4.mol

Synonyms:METHYL 2-(1-TOSYL-1H-IMIDAZOL-4-YL)ACETATE;497159-97-4;Methyl 2-[1-(4-methylphenyl)sulfonylimidazol-4-yl]acetate;SCHEMBL7261526;DTXSID60463137;MFCD08275083;AB44709;F97422

Chemical Property of Methyl 2-(1-tosyl-1H-imidazol-4-YL)acetate

Chemical Property:

• PSA: 86.64000
• LogP: 2.22480
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 5
• Exact Mass: 294.06742811
• Heavy Atom Count: 20
• Complexity: 438

Purity/Quality:

98%min ^*data from raw suppliers

METHYL-2-(1-TOSYL-1H-IMIDAZOL-4-YL)ACETATE 95.00% ^*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)N2C=C(N=C2)CC(=O)OC

Technology Process of Methyl 2-(1-tosyl-1H-imidazol-4-YL)acetate

There total 2 articles about Methyl 2-(1-tosyl-1H-imidazol-4-YL)acetate 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:

methyl 2-(1H-imidazol-4-yl)acetate hydrochloride (51718-80-0) + p-toluenesulfonyl chloride (98-59-9) → methyl {1-[(4-methylphenyl)sulfonyl]-1H-imidazol-4-yl}acetate (497159-97-4)

Guidance literature:

With triethylamine; In dichloromethane; for 0.5h;

DOI:10.1021/jm034141y

Reference yield:

imidazole-4-acetic acid hydrochloride (3251-69-2) → methyl {1-[(4-methylphenyl)sulfonyl]-1H-imidazol-4-yl}acetate (497159-97-4)

Guidance literature:

Multi-step reaction with 2 steps

1: HCl / 16 h / 0 °C

2: 7 g / triethylamine / CH₂Cl₂ / 0.5 h

With hydrogenchloride; triethylamine; In dichloromethane;

DOI:10.1021/jm034141y

Reference yield: 50.0%

methyl cyanoformate (17640-15-2) + methyl {1-[(4-methylphenyl)sulfonyl]-1H-imidazol-4-yl}acetate (497159-97-4) → dimethyl 2-{1-[(4-methylphenyl)sulfonyl]-1H-imidazol-4-yl}malonate (497159-98-5)

Guidance literature:

methyl {1-[(4-methylphenyl)sulfonyl]-1H-imidazol-4-yl}acetate; With lithium hexamethyldisilazane; In tetrahydrofuran; at 0 ℃; for 0.5h;

methyl cyanoformate; In tetrahydrofuran; at 0 - 20 ℃;

DOI:10.1021/jm034141y

upstream raw materials:

methyl 2-(1H-imidazol-4-yl)acetate hydrochloride

p-toluenesulfonyl chloride

imidazole-4-acetic acid hydrochloride

Downstream raw materials:

dimethyl 2-{1-[(4-methylphenyl)sulfonyl]-1H-imidazol-4-yl}malonate

3-(6-amino-pyridin-3-yl)-2-(1-benzyl-1H-imidazol-4-yl)-propionic acid ethyl ester

dimethyl 2-({6-[(tert-butoxycarbonyl)amino]pyridin-3-yl}methyl)-2-{1-[(4-methylphenyl)sulfonyl]-1H-imidazol-4-yl}malonate

3-(6-tert-butoxycarbonylamino-pyridin-3-yl)-2-[1-(toluene-4-sulfonyl)-1H-imidazol-4-yl]-propionic acid methyl ester