Ethotoin

Base Information

• Chemical Name: Ethotoin
• CAS No.: 86-35-1
• Molecular Formula: C11H12 N2 O2
• Molecular Weight: 204.228
• Hs Code.: 2933210000
• European Community (EC) Number: 201-665-1
• NSC Number: 760074
• UNII: 46QG38NC4U
• DSSTox Substance ID: DTXSID6023020
• Nikkaji Number: J3.894F
• Wikipedia: Ethotoin
• Wikidata: Q4533122
• NCI Thesaurus Code: C47524
• Pharos Ligand ID: YRK52NMJFWP6
• Metabolomics Workbench ID: 144288
• ChEMBL ID: CHEMBL1095
• Mol file: 86-35-1.mol

Synonyms:ethotoin;Peganone

Chemical Property of Ethotoin

Chemical Property:

• Melting Point: 94°C
• Refractive Index: 1.5200 (estimate)
• Boiling Point: 342.72°C (rough estimate)
• PKA: 8.01±0.70(Predicted)
• PSA: 52.90000
• Density: 1.197 g/cm1.197 g/cm3
• LogP: 0.87730
• Storage Temp.: Refrigerator
• Solubility.: Dichloromethane (Slightly), DMSO (Slightly), Methanol (Slightly)
• XLogP3: 1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 204.089877630
• Heavy Atom Count: 15
• Complexity: 272

Purity/Quality:

99% ^*data from raw suppliers

Ethotoin ^*data from reagent suppliers

Safty Information:

• Statements: 22

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCN1C(=O)C(NC1=O)C2=CC=CC=C2
• Uses: Ethotoin is less active and less toxic than phenytoin. It is used for the same indications as is phenytoin, i.e. for control of major and complex epileptic attacks. Ethotoin is a hydantoin based anticonvulsant drug used in the treatment of epilepsy.
• Therapeutic Function: Anticonvulsant

Technology Process of Ethotoin

There total 5 articles about Ethotoin 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: 78.0%

N-ethylcarbamicacid phenylester (17576-39-5) + L-2-phenylglycine methyl ester hydrochloride (15028-39-4,13226-98-7) → ethotoin (86-35-1,108739-43-1,41807-37-8)

Guidance literature:

N-ethylcarbamicacid phenylester; L-2-phenylglycine methyl ester hydrochloride; With triethylamine; In acetonitrile; for 10h; Reflux;

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

DOI:10.1055/s-0036-1588468

Reference yield: 60.0%

C15H22N2O3 → ethotoin (86-35-1,108739-43-1,41807-37-8)

Guidance literature:

With pyridine; trifluoromethylsulfonic anhydride; In dichloromethane; at 4 - 25 ℃; for 2.08333h; Inert atmosphere;

DOI:10.1021/ol502900j

Reference yield:

2-(tert-butoxycarbonylamino)-2-phenylacetic acid (2900-27-8,3601-66-9,14675-97-9,33125-05-2) → ethotoin (86-35-1,108739-43-1,41807-37-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / Inert atmosphere

2: trifluoromethylsulfonic anhydride; pyridine / dichloromethane / 2.08 h / 4 - 25 °C / Inert atmosphere

With pyridine; trifluoromethylsulfonic anhydride; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane;

DOI:10.1021/ol502900j

upstream raw materials:

(S)-2-phenylglycine

ethyl isocyanate

ethyl bromide

2-(tert-butoxycarbonylamino)-2-phenylacetic acid

Downstream raw materials:

ethylamine

phenylglycin

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

Refernces

• 1、 Liu, Hui,Yang, Zhimin,Pan, Zhengying. "Synthesis of highly substituted imidazolidine-2,4-dione (Hydantoin) through Tf2O-mediated dual activation of Boc-protected dipeptidyl compounds". supporting information. p. 5902 - 5905. Retrieved 2015/01/08.