3-Methyl-5-phenylhydantoin

Base Information

• Chemical Name: 3-Methyl-5-phenylhydantoin
• CAS No.: 6846-11-3
• Molecular Formula: C10H10N2O2
• Molecular Weight: 190.202
• UNII: R04D61Y6L4
• DSSTox Substance ID: DTXSID10988108
• Wikidata: Q27287591
• ChEMBL ID: CHEMBL90302
• Mol file: 6846-11-3.mol

Synonyms:Nuvarone;3-Methyl-5-phenylhydantoin;R04D61Y6L4;6846-11-3;UNII-R04D61Y6L4;2,4-Imidazolidinedione, 3-methyl-5-phenyl-;NORANTOIN;SCHEMBL77736;CHEMBL90302;DTXSID10988108;AKOS017265180;HYDANTOIN, 3-METHYL-5-PHENYL-;3-METHYL-5-PHENYLHYDANTOIN [MI];PD159931;3-methyl-5-phenyl-2,4-imidazolidinedione;Q27287591;2-Hydroxy-3-methyl-5-phenyl-3,5-dihydro-4H-imidazol-4-one

Chemical Property of 3-Methyl-5-phenylhydantoin

Chemical Property:

• Density: 1.243g/cm³
• XLogP3: 0.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 190.074227566
• Heavy Atom Count: 14
• Complexity: 259

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN1C(=O)C(NC1=O)C2=CC=CC=C2

Technology Process of 3-Methyl-5-phenylhydantoin

There total 7 articles about 3-Methyl-5-phenylhydantoin 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: 90.0%

5-phenylimidazolidine-2,4-dione (89-24-7,27534-86-7) + N,N-dimethyl-formamide dimethyl acetal (4637-24-5) → 3-methyl-5-phenylimidazolidine-2,4-dione (6846-11-3)

Guidance literature:

at 100 ℃; for 1h;

DOI:10.1002/bscb.19850940611

Reference yield: 72.0%

N-Methyl-O-phenylcarbamat (1943-79-9) + L-2-phenylglycine methyl ester hydrochloride (15028-39-4,13226-98-7) → 3-methyl-5-phenylimidazolidine-2,4-dione (6846-11-3)

Guidance literature:

N-Methyl-O-phenylcarbamat; L-2-phenylglycine methyl ester hydrochloride; With triethylamine; In acetonitrile; for 10h; Reflux;

With sodium hydroxide; In acetonitrile; for 8h; Reflux;

DOI:10.1055/s-0036-1588468

Reference yield:

methyl iodide (74-88-4) → 3-methyl-5-phenylimidazolidine-2,4-dione (6846-11-3)

Guidance literature:

With ethanol; at 100 ℃; im Rohr;

upstream raw materials:

5-phenylimidazolidine-2,4-dione

N,N-dimethyl-formamide dimethyl acetal

N-(cyano-phenyl-methyl)-N'-methyl-urea

phenylglyoxal hydrate

Downstream raw materials:

1-methyl-4-phenyl-1,3-dihydro-imidazol-2-one

1,1'-dimethyl-4,4'-diphenyl-tetrahydro-[4,4']biimidazolyl-2,5,2',5'-tetraone

1-methyl-4-phenylimidazolidin-2-one

N-methyl-4-phenylimidazole

Refernces

• 1、 Machacek, Vladimir,Svobodova, Gabriela,Sterba, Vojeslav. "KINETICS AND MECHANISM OF BASE-CATALYZED CYCLIZATION OF SUBSTITUTED AMIDES AND NITRILES OF HYDANTOIC ACID". . p. 140 - 155. Retrieved 2007/10/02.