4-Oxazolecarboxylic acid, 5-(4-chlorophenyl)-, methyl ester

Base Information

• Chemical Name: 4-Oxazolecarboxylic acid, 5-(4-chlorophenyl)-, methyl ester
• CAS No.: 89204-93-3
• Molecular Formula: C11H8ClNO3
• Molecular Weight: 237.642
• DSSTox Substance ID: DTXSID20474365
• Wikidata: Q82304347
• Mol file: 89204-93-3.mol

Synonyms:89204-93-3;4-Oxazolecarboxylic acid, 5-(4-chlorophenyl)-, methyl ester;Methyl 5-(4-chlorophenyl)-1,3-oxazole-4-carboxylate;Methyl 5-(4-chlorophenyl)oxazole-4-carboxylate;SCHEMBL1931754;DTXSID20474365;MGGPQBAELYVXMR-UHFFFAOYSA-N

Chemical Property of 4-Oxazolecarboxylic acid, 5-(4-chlorophenyl)-, methyl ester

Chemical Property:

• PSA: 52.33000
• LogP: 2.78160
• XLogP3: 2.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 237.0192708
• Heavy Atom Count: 16
• Complexity: 254

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C1=C(OC=N1)C2=CC=C(C=C2)Cl

Technology Process of 4-Oxazolecarboxylic acid, 5-(4-chlorophenyl)-, methyl ester

There total 5 articles about 4-Oxazolecarboxylic acid, 5-(4-chlorophenyl)-, methyl ester 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: 65.0%

N-[2-(4-chlorophenyl)-1-methoxycarbonyl-2-oxoethyl]formamide (119826-04-9) → 5-(4-chlorophenyl)oxazole-4-carboxylic acid methyl ester (89204-93-3)

Guidance literature:

With iodine; triethylamine; triphenylphosphine; In dichloromethane; for 16h;

DOI:10.1016/j.tet.2004.03.037

Reference yield: 45.0%

methyl 2-isocyanatoacetate (30988-17-1) + 4-chloro-benzoyl chloride (122-01-0) → 5-(4-chlorophenyl)oxazole-4-carboxylic acid methyl ester (89204-93-3)

Guidance literature:

With triethylamine; In tetrahydrofuran; at 20 ℃; for 48h;

Reference yield:

methyl 3-(4-chlorophenyl)-3-oxopropanoate (22027-53-8) → 5-(4-chlorophenyl)oxazole-4-carboxylic acid methyl ester (89204-93-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 89 percent / 4-acetamidobenzenesulfonyl azide; triethylamine / acetonitrile / 16 h / 20 °C

2: 55 percent / dirhodium tetraoctanoate / CH₂Cl₂ / Heating

3: 65 percent / triphenylphosphine; iodine; triethylamine / CH₂Cl₂ / 16 h

With 4-acetamidobenzenesulfonyl azide; iodine; triethylamine; triphenylphosphine; rhodium (II) octanoate dimer; In dichloromethane; acetonitrile;

DOI:10.1016/j.tet.2004.03.037

upstream raw materials:

N-[2-(4-chlorophenyl)-1-methoxycarbonyl-2-oxoethyl]formamide

isocyanoacetic acid methyl ester

4-chloro-benzoyl chloride

methyl 3-(4-chlorophenyl)-3-oxopropanoate

Downstream raw materials:

5-(4-chlorophenyl)oxazole-4-carboxylic acid

5-(4-chlorophenyl)oxazole-4-carboxamide

5-chlorophenyl-N-[1-methoxycarbonyl-2-oxopropyl]oxazole-4-carboxamide

4-(chloromethyl)-5-(4-chlorophenyl)-1,3-oxazole