ethyl 5-methyl-2-phenyl-1H-imidazole-4-carboxylate

Base Information

• Chemical Name: ethyl 5-methyl-2-phenyl-1H-imidazole-4-carboxylate
• CAS No.: 77335-93-4
• Molecular Formula: C13H14 N2 O2
• Molecular Weight: 230.266
• Hs Code.: 2933290090
• DSSTox Substance ID: DTXSID50507519
• Wikidata: Q82363785
• Mol file: 77335-93-4.mol

Synonyms:ethyl 5-methyl-2-phenyl-1H-imidazole-4-carboxylate;77335-93-4;Ethyl 4-methyl-2-phenyl-1H-imidazole-5-carboxylate;1260859-49-1;4-methyl-2-phenyl-1h-imidazole-5-carboxylic acid Ethyl ester;5-METHYL-2-PHENYL-3H-IMIDAZOLE-4-CARBOXYLIC ACID ETHYL ESTER;SCHEMBL15442034;DTXSID50507519;AMY27510;MFCD08276084;MFCD09759050;AKOS000321205;AKOS027381428;LS-01082;SY082630;BB 0240585;FT-0712763;5-Methyl-2-phenyl-1H-imidazole-4-carboxylic acid ethyl ester

Chemical Property of ethyl 5-methyl-2-phenyl-1H-imidazole-4-carboxylate

Chemical Property:

• PSA: 54.98000
• LogP: 2.56180
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 230.105527694
• Heavy Atom Count: 17
• Complexity: 264

Purity/Quality:

98%min ^*data from raw suppliers

Ethyl 5-methyl-2-phenyl-1H-imidazole-4-carboxylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C1=C(NC(=N1)C2=CC=CC=C2)C

Technology Process of ethyl 5-methyl-2-phenyl-1H-imidazole-4-carboxylate

There total 11 articles about ethyl 5-methyl-2-phenyl-1H-imidazole-4-carboxylate 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: 42.0%

benzylamine (100-46-9) + ethyl 2-hydroxyimino-3-oxobutanoate (5408-04-8) → ethyl 4-methyl-2-phenyl-1H-imidazole-5-carboxylate (77335-93-4)

Guidance literature:

In acetonitrile; for 5h; Reflux;

Reference yield: 31.0%

benzylamine (100-46-9) + ethyl 2-hydroxyimino-3-oxobutanoate (5408-04-8) → ethyl 5-methyl-2-phenyl-1H-imidazole-4-carboxylate (77335-93-4)

Guidance literature:

In acetonitrile; for 3h; Heating;

Reference yield:

(±)-ethyl 3-methyl-2H-azirine-2-carboxylate (14369-88-1) + benzimidic acid ethyl ester (825-60-5) → ethyl 5-methyl-2-phenyl-1H-imidazole-4-carboxylate (77335-93-4) + ethyl 4-methyl-2-phenyl-1H-imidazole-5-carboxylate (77335-93-4)

Guidance literature:

With zinc(II) chloride; In acetonitrile; at 80 ℃; for 12h; Overall yield = 71 %; Overall yield = 50 mg; Schlenk technique;

DOI:10.1021/acs.joc.8b02437

upstream raw materials:

ethyl 2-amino-3-oxobutanoate hydrochloride

methyl benzimidate

benzylamine

ethyl 2-hydroxyimino-3-oxobutanoate

Downstream raw materials:

5-methyl-2-phenyl-1⁽³⁾H-imidazole-4-carboxylic acid

4-methyl-2-phenyl-1H-imidazole

C₂₀H₁₈N₂OS₂

C₂₀H₁₈N₂O₂S₂

Refernces

• 1、 Hsu, Mei-Yuan,Dietrich, Justin,Hulme, Christopher,Shaw, Arthur Y.. "Synthesis of di- and tri-substituted imidazole-4-carboxylates via PBu3-mediated [3+2] cycloaddition". . p. 1538 - 1542. Retrieved 2013/05/21.
• 2、 Potter, Andrew,Oldfield, Victoria,Nunns, Claire,Fromont, Christophe,Ray, Stuart,Northfield, Christopher J.,Bryant, Christopher J.,Scrace, Simon F.,Robinson, David,Matossova, Natalia,Baker, Lisa,Dokurno, Pawel,Surgenor, Allan E.,Davis, Ben,Richardson, Christine M.,Murray, James B.,Moore, Jonathan D.. "Discovery of cell-active phenyl-imidazole Pin1 inhibitors by structure-guided fragment evolution". scheme or table. p. 6483 - 6488. Retrieved 2010/12/18.