86-35-1 Usage
Originator
Peganone,Abbott,US,1957
Manufacturing Process
Benzaldehyde cyanohydrin is reacted with urea to displace the hydroxyl group
of the cyanohydrin. That intermediate is treated with HCl to convert the urea
nitrogen to a nitrile. The resultant imine is hydrolyzed to the phenylhydantoin.
Alkylation with ethyl iodide gives ethotoin, as described by A. Pinner in Chem.
Ber. 21, 2325 (1888).
Therapeutic Function
Anticonvulsant
Synthesis
Ethotoin, 3-ethyl-5-phenylimidazolidine-2,4-dione (9.1.5), is synthesized in
basically the same manner as described above, which in this case involves the reaction of
benzaldehyde oxynitrile (9.1.2), with urea or ammonium hydrocarbonate, which forms
the intermediate urea derivative (9.1.3) which on acidic conditions (9.1.3) cyclizes to
5-phenylhydantoin (9.1.4). Alkylation of this product using ethyliodide leads to the formation of ethotoin (9.1.5) [3,4].
Metabolism
Ethotoin differs from phenytoin in that one phenyl substituent at position 5 has been replaced by hydrogen, and the N-H at
position 3 is replaced by an ethyl group. It may be indicated for treatment of tonic-clonic and complex partial
(psychomotor) seizures. Because it is considered to be less toxic but also less effective and more sedating than phenytoin,
ethotoin usually is reserved for use as an add-on drug. Ethotoin does not share phenytoin's profile of antiarrhythmic
action. The metabolism of ethotoin, like phenytoin, is saturable and nonlinear. Its administration is contraindicated in patients
with hepatic abnormalities and hematologic disorders.
Purification Methods
It is an anticonvulsant and is used in epilepsy. [Dudley et al. J Heterocycl Chem 10 173 1973, Pinner Chem Ber 21 2320 1888, Beilstein 25 III/IV 963, 27 II 860.]
Check Digit Verification of cas no
The CAS Registry Mumber 86-35-1 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 8 and 6 respectively; the second part has 2 digits, 3 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 86-35:
(4*8)+(3*6)+(2*3)+(1*5)=61
61 % 10 = 1
So 86-35-1 is a valid CAS Registry Number.
InChI:InChI=1/C11H12N2O2/c1-2-13-10(14)9(12-11(13)15)8-6-4-3-5-7-8/h3-7,9H,2H2,1H3,(H,12,15)
86-35-1Relevant academic research and scientific papers
Facile One-Pot Synthesis of Substituted Hydantoins from Carbamates
Tanwar, Dinesh Kumar,Ratan, Anjali,Gill, Manjinder Singh
supporting information, p. 2285 - 2290 (2017/10/06)
A novel and simple approach for the preparation of 3-substituted, 5-substituted, or 3,5-disubstituted hydantoins is reported. It involves the reaction of α-amino methyl ester hydrochlorides with carbamates to yield the corresponding ureido derivatives, which subsequently cyclize under basic conditions to produce substituted hydantoins in good yields. By applying this method, the bioactive anticonvulsant drug ethotoin was synthesized in good yield. The process avoids conventional multistep protocols and does not use the hazardous, irritant, toxic, or moisture-sensitive reagents, such as isocyanates or chloroformates, that are commonly used for the synthesis of these important compounds.
Synthesis of highly substituted imidazolidine-2,4-dione (Hydantoin) through Tf2O-mediated dual activation of Boc-protected dipeptidyl compounds
Liu, Hui,Yang, Zhimin,Pan, Zhengying
supporting information, p. 5902 - 5905 (2015/01/08)
Highly substituted chiral hydantoins were readily synthesized from simple dipeptides in a single step under mild conditions. This reaction proceeded through the dual activation of an amide and a tert-butyloxycarbonyl (Boc) protecting group by Tf2O-pyridine. This method was successfully applied in the preparation of a variety of biologically active compounds, including drug analogs and natural products.
