5394-36-5

Basic information

• Product Name: 5-Ethyl-5-methylimidazolidine-2,4-dione
• Synonyms: 5-ETHYL-5-METHYLHYDANTOIN;5-ETHYL-5-METHYLIMIDAZOLIDINE-2,4-DIONE;5-Methyl-5-ethyl-2,4-imidazolidinedione;NSC 1020
• CAS NO: 5394-36-5
• Molecular Formula: C₆H₁₀N₂O₂
• Molecular Weight: 142.16
• EINECS: 226-402-8
• Mol File: 5394-36-5.mol

Chemical Properties

• Melting Point: 144-150 ºC
• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: 1.095 g/cm³
• Storage Temp.: 2-8°C
• PKA: 8.93±0.10(Predicted)
• CAS DataBase Reference: 5-Ethyl-5-methylimidazolidine-2,4-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Ethyl-5-methylimidazolidine-2,4-dione(5394-36-5)
• EPA Substance Registry System: 5-Ethyl-5-methylimidazolidine-2,4-dione(5394-36-5)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• WGK Germany: 3
• RTECS: MU2070000
• Hazardous Substances Data: 5394-36-5(Hazardous Substances Data)

Usage

Uses

Reactant for synthesis of nociceptin/orphanin FQ analogues

InChI:InChI=1/C6H10N2O2/c1-3-6(2)4(9)7-5(10)8-6/h3H2,1-2H3,(H2,7,8,9,10)

Synthetic route

tetra-n-butylammonium cyanide (10442-39-4) + ammonium carbonate (506-87-6) + butanone (78-93-3) → 5-ethyl-5-methylimidazolidine-2,4-dione (5394-36-5)

Conditions	Yield
In ethanol; water for 40h; Heating;	50%

(1-cyano-1-methyl-propyl)-urea → 5-ethyl-5-methylimidazolidine-2,4-dione (5394-36-5)

Conditions	Yield
With hydrogenchloride

2-amino-2-methylbutanenitrile (4475-95-0) → 5-ethyl-5-methylimidazolidine-2,4-dione (5394-36-5)

Conditions	Yield
With carbon dioxide; water

2-hydroxy-2-methyl-butyronitrile (4111-08-4) → 5-ethyl-5-methylimidazolidine-2,4-dione (5394-36-5)

Conditions	Yield
With ammonium carbonate at 90℃;

2-cyano-2-methyl-butyric acid amide → 5-ethyl-5-methylimidazolidine-2,4-dione (5394-36-5)

Conditions	Yield
With potassium hypobromite inactive form;

N-(2-amino-2-methyl-butyryl)-N'-(3,5-diethyl-2-imino-5-methyl-pyrrolidin-3-yl)-urea → 3,5-diethyl-2-imino-5-methyl-pyrrolidin-3-ylamine (98957-58-5) + 5-ethyl-5-methylimidazolidine-2,4-dione (5394-36-5)

Conditions	Yield
With hydrogenchloride

hydrogen cyanide (74-90-8) + butanone (78-93-3) → 5-ethyl-5-methylimidazolidine-2,4-dione (5394-36-5)

Conditions	Yield
beim Belichten; inactive form;

2-amino-2-methylbutanenitrile (4475-95-0) + 2CO3 → 5-ethyl-5-methylimidazolidine-2,4-dione (5394-36-5)

Conditions	Yield
With water

potassium cyanide (151-50-8) + butanone (78-93-3) + 2CO3 → 5-ethyl-5-methylimidazolidine-2,4-dione (5394-36-5)

Conditions	Yield
With ethanol

potassium cyanate (590-28-3) + l-isovaline → 5-ethyl-5-methylimidazolidine-2,4-dione (5394-36-5)

Conditions	Yield
Abdampfen des entstandenen Harnstoffderivats mit verd. Salzsaeure; active form;

formamide (77287-34-4, 77287-35-5, 60100-09-6) + butanone (78-93-3) + aluminium oxide → 2-amino-2-methylbutanenitrile (4475-95-0) + 5-ethyl-5-methylimidazolidine-2,4-dione (5394-36-5)

Conditions	Yield
at 350℃;
at 350 - 360℃;

2-hydroxy-2-methyl-butyronitrile (4111-08-4) + ammonium carbonate (506-87-6) → 5-ethyl-5-methylimidazolidine-2,4-dione (5394-36-5)

Conditions	Yield
Heating / reflux;

potassium cyanide + ammonium carbonate (506-87-6) + butanone (78-93-3) → 5-ethyl-5-methylimidazolidine-2,4-dione (5394-36-5)

Conditions	Yield
Stage #1: butanone With sodium metabisulfite Stage #2: potassium cyanide Bucherer-Bergs reaction; Stage #3: ammonium carbonate Bucherer-Bergs reaction;

methyloxirane (75-56-9, 16033-71-9) + 5-ethyl-5-methylimidazolidine-2,4-dione (5394-36-5) → 5-ethyl-1,3-bis-(2-hydroxy-propyl)-5-methyl-imidazolidine-2,4-dione (29810-32-0)

Conditions	Yield
With hydrogenchloride; lithium chloride In N-methyl-acetamide	99.5%

4-chlorobutyl bromide (6940-78-9) + 5-ethyl-5-methylimidazolidine-2,4-dione (5394-36-5) → 3-(4-chlorobutyl)-5-ethyl-5-methylimidazolidine-2,4-dione

Conditions	Yield
With potassium hydroxide In ethanol for 15h; Heating;	81%

iodobenzene (591-50-4) + 5-ethyl-5-methylimidazolidine-2,4-dione (5394-36-5) → 5-ethyl-5-methyl-3-phenylhydantoin (36027-16-4)

Conditions	Yield
With copper(I) oxide In N,N-dimethyl-formamide at 150℃; for 14h; Inert atmosphere; regioselective reaction;	68%

5-ethyl-5-methylimidazolidine-2,4-dione (5394-36-5) + methyl iodide (74-88-4) → 5-ethyl-3,5-dimethyl-imidazolidine-2,4-dione (6843-47-6)

Conditions	Yield
With potassium hydroxide; ethanol

5-ethyl-5-methylimidazolidine-2,4-dione (5394-36-5) → DL-isovaline (595-39-1)

Conditions	Yield
With barium dihydroxide Heating;
(hydrolysis);
With barium hydroxide octahydrate; water at 140℃; for 48h;

5-ethyl-5-methylimidazolidine-2,4-dione (5394-36-5) + methyl iodide (74-88-4) → 5-ethyl-1,3,5-trimethylhydantoin

Conditions	Yield
With pH 13 buffer

hydrogenchloride (7647-01-0) + 5-ethyl-5-methylimidazolidine-2,4-dione (5394-36-5) → DL-isovaline (595-39-1)

Conditions	Yield
im Rohr; inactive form;

5-ethyl-5-methylimidazolidine-2,4-dione (5394-36-5) → 3-{4-[Bis-(2-chloro-ethyl)-amino]-butyl}-5-ethyl-5-methyl-imidazolidine-2,4-dione

Conditions	Yield
Multi-step reaction with 3 steps 1: 81 percent / KOH / aq. ethanol / 15 h / Heating 2: 68 percent 3: 28 percent / POCl3 View Scheme

5-ethyl-5-methylimidazolidine-2,4-dione (5394-36-5) → 3-{4-[Bis-(2-hydroxy-ethyl)-amino]-butyl}-5-ethyl-5-methyl-imidazolidine-2,4-dione

Conditions	Yield
Multi-step reaction with 2 steps 1: 81 percent / KOH / aq. ethanol / 15 h / Heating 2: 68 percent View Scheme

active charcoal + 5-ethyl-5-methylimidazolidine-2,4-dione (5394-36-5) → 3-[2-(Vinyloxy)-ethyl]-5-methyl-5-ethyl-hydantoin (69850-89-1)

Conditions	Yield
With potassium carbonate In N-methyl-acetamide; acetone

iodobenzene (591-50-4) + 5-ethyl-5-methylimidazolidine-2,4-dione (5394-36-5) → 5-ethyl-5-methyl-1,3-diphenylhydantoin

Conditions	Yield
Multi-step reaction with 2 steps 1: copper(I) oxide / N,N-dimethyl-formamide / 14 h / 150 °C / Inert atmosphere 2: copper(l) iodide; potassium carbonate; trans-N,N'-dimethylcyclohexane-1,2-diamine / toluene / 48 h / 110 °C / Inert atmosphere View Scheme

Upstream product

• 4475-95-0 2-amino-2-methylbutanenitrile 
• 4111-08-4 2-hydroxy-2-methyl-butyronitrile 
• 74-90-8 hydrogen cyanide 
• 78-93-3 butanone 
• 151-50-8 potassium cyanide 
• 590-28-3 potassium cyanate 
• 77287-34-4 formamide 
• 506-87-6 ammonium carbonate 
• 10442-39-4 tetra-n-butylammonium cyanide 

Downstream Products

• 595-39-1 DL-isovaline 
• 36027-16-4 5-ethyl-5-methyl-3-phenylhydantoin 

Relevant articles and documents

AMIDOALKYLPIPERAZINYL DERIVATIVES FOR THE TREATMENT OF CENTRAL NERVOUS SYSTEM DISEASES

The invention relates to novel amidoalkylpiperazinyl derivatives of tricyclic heterocyclic systems of general formula (I), wherein Z represents -NH- and X represents -S-, or Z represents -S- and X represents >C=C1 represents H or -CH3, R6 and R7 both represent H, n is an integer from 0 to 4 inclusive, G represents a cyclic amide or imide moiety, and optical isomers, geometric isomers, and pharmaceutically acceptable salts thereof. The compounds may be useful for the treatment and/or prevention of the central nervous system disorders.

New polyamides based on 1,3-bis(4-carboxy phenoxy) propane and hydantoin derivatives: Synthesis and properties

Six new polyamides 5a-f containing flexible trimethylene segments in the main chain were synthesized through the direct polycondensation reaction of 1,3-bis(4-carboxy phenoxy) propane 3 with six derivatives of hydantoins 4a-f in a medium consisting of N-methyl-2-pyrrolidone, triphenyl phosphite, calcium chloride and pyridine. The polycondensation reaction produced a series of novel polyamides in high yield with inherent viscosities between 0.30-0.47 dL/g. The resulted polymers were fully characterized by means of FT-IR, 1H-NMR spectroscopy, elemental analyses, inherent viscosity, solubility tests and gel permeation chromatography (GPC). Thermal properties of these polymers were investigated by using thermal gravimetric analysis (TGA) and differential thermal gravimetry (DTG). The glass-transition temperatures of these polyamides were recorded between 130 and 155 °C by differential scanning catorimetry (DSC), and the 5% weight loss temperatures were ranging from 325 to 415 °C under nitrogen. 1,3-bis(4-Carboxy phenoxy) propane 3 was prepared from the reaction of 4-hydroxy benzoic acid 1 with 1,3-dibromo propane 2 in the presence of NaOH solution.

PROCESS FOR STRAIGHTENING KERATIN FIBRES WITH A HEATING MEANS AND DENATURING AGENTS

The invention relates to a process for straightening keratin fibres, comprising: (i) a step in which a straightening composition containing at least two denaturing agents is applied to the keratin fibres, (ii) a step in which the temperature of the keratin fibres is raised, using a heating means, to a temperature of between 110 and 250° C.

BIOFILM CONTROL

Compositions and methods suitable for killing bacteria and controlling biofilms comprising one or more microorganisms are provided wherein molecules capable of emulating cell-to-cell signal molecules of the microorganisms are utilized.

Synthesis and biological activity of nociceptin/orphanin FQ analogues substituted in position 7 or 11 with Cα,α-dialkylated amino acids

Previous structure-activity and NMR studies on nociceptin/orphanin FQ (N/OFQ) demonstrated that Aib substitution of Ala7 and/or Ala11 increases the peptide potency through an alpha helix structure induction mechanism. On these bases we synthesised and evaluated pharmacologically in the mouse vas deferens assay a series of N/OFQ-NH2 analogues substituted in position 7 and 11 with Cα,α-disubstituted cyclic, linear and branched amino acids. None of the 20 novel N/OFQ analogues produced better results than [Aib7]N/OFQ-NH2. Thus, this substitution was combined with other chemical modifications known to modulate peptide potency and/or efficacy generating compound 21 [Nphe1Aib7Arg14Lys15]N/OFQ-NH2 (coded as UFP-111), compound 22 [(pF)Phe4Aib7Arg14Lys15]N/OFQ-NH2 (UFP-112) and compound 23 [Phe1Ψ(CH2-NH)Gly2(pF)Phe4Aib7Arg14Lys15]N/OFQ-NH2 (UFP-113). These novel peptides behaved as highly potent NOP receptor ligands showing full (UFP-112) and partial (UFP-113) agonist and pure antagonist (UFP-111) activities in a series of in vitro functional assays performed on pharmacological preparations expressing native as well as recombinant NOP receptors.