5391-39-9

Basic information

• Product Name: 1-Acetyl-2-imidazolidinone
• Synonyms: 1-ethanoylimidazolidin-2-one;N-acetyl-2-iMidazolidazolidinone;Clonidine IMpurity-A(BP);Clonidine Impurity A;2-Imidazolidinone,1-acetyl-;n-acetyl-2-imidazolidinone;RARECHEM AQ NN 0041;ACETYL IMIDAZO-2-ONE
• CAS NO: 5391-39-9
• Molecular Formula: C₅H₈N₂O₂
• Molecular Weight: 128.13
• EINECS: 226-388-3
• Product Categories: Imidazol&Benzimidazole;(intermediate of moxonidine hcl)
• Mol File: 5391-39-9.mol
• Article Data: 12

Chemical Properties

• Melting Point: 173-175°C
• Appearance: /
• Density: 1.237
• Refractive Index: 1.492
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: Chloroform (Sparingly), DMSO (Sparingly), Methanol (Slightly, Heated)
• PKA: 12.11±0.20(Predicted)
• CAS DataBase Reference: 1-Acetyl-2-imidazolidinone(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Acetyl-2-imidazolidinone(5391-39-9)
• EPA Substance Registry System: 1-Acetyl-2-imidazolidinone(5391-39-9)

Safety Data

• Hazardous Substances Data: 5391-39-9(Hazardous Substances Data)

Usage

Uses

1-Acetyl-2-imidazolidinone (Clonidine EP Impurity A) is a synthetic reagent used in the preparation of triple [14C]-labelled moxonidine which is an antihypertensive compound.

InChI:InChI=1/C5H8N2O2/c1-4(8)7-3-2-6-5(7)9/h2-3H2,1H3,(H,6,9)

Synthetic route

imidazolidone (120-93-4) + acetic anhydride (108-24-7) → 1-acetylimidazolidin-2-one (5391-39-9)

Conditions	Yield
With water for 0.5h; Heating;	88%
at 150℃; for 1h;	64.1%
for 0.5h; Reflux;	63%

imidazolidone (120-93-4) + 1-acetyl-1H-benzotriazole (18773-93-8) → 1-acetylimidazolidin-2-one (5391-39-9)

Conditions	Yield
Stage #1: imidazolidone With potassium carbonate In toluene at 20℃; for 0.5h; Stage #2: 1-acetyl-1H-benzotriazole In toluene at 80℃; for 2h;	87%

imidazolidone (120-93-4) + Benzyl isocyanide (88333-03-3, 10340-91-7) + acetyl chloride (75-36-5) → 1-acetylimidazolidin-2-one (5391-39-9) + 1-(benzyliminomethyl)imidazolin-2-one hydrochloride

Conditions	Yield
In acetonitrile at 20℃; for 9h;	A n/a B 77%

imidazol-2-one (65118-65-2) + acetyl chloride (75-36-5) → 1-acetylimidazolidin-2-one (5391-39-9)

Conditions	Yield
In tetrahydrofuran	52%
In tetrahydrofuran	52%
In tetrahydrofuran	52%
In tetrahydrofuran	52%

monoacetylaminoethylamine (1001-53-2) + carbon dioxide (124-38-9) → 1-acetylimidazolidin-2-one (5391-39-9)

Conditions	Yield
With cerium(IV) oxide In ethanol at 160℃; for 8h;	9%

1-acetylimidazolidin-2-one (5391-39-9) + Vinyl bromide (593-60-2) → 1-acetyl-3-vinyl-2-imidazolidone

Conditions	Yield
With copper(l) iodide; potassium carbonate; N,N`-dimethylethylenediamine In tetrahydrofuran at 80℃; for 9h; Inert atmosphere; Schlenk technique;	94.4%

1-acetylimidazolidin-2-one (5391-39-9) + bis(trichloromethyl) carbonate (32315-10-9) → 1-chlorocarbonyl-2-oxo-3-methylcarbonyl-imidazolidine (41730-71-6)

Conditions	Yield
In benzene at 55 - 60℃; for 3h; chloroformylation;	93.8%

1-acetylimidazolidin-2-one (5391-39-9) + 4-amino-5-chloro-2,1,3-benzothiadiazole (30536-19-7) → 5-chloro-N-(1-acetyl-4,5-dihydro-1H-imidazol-2-yl)-2,1,3-benzothiadiazole-4-amine

Conditions	Yield
With trichlorophosphate In acetone at 50 - 55℃; for 20h; Temperature; Solvent;	93.6%
With thionyl chloride In toluene at 65℃; Reagent/catalyst; Solvent;	67%

1-acetylimidazolidin-2-one (5391-39-9) + trichloromethyl chloroformate (503-38-8) → 1-chlorocarbonyl-2-oxo-3-methylcarbonyl-imidazolidine (41730-71-6)

Conditions	Yield
With pyridine In benzene at 50 - 55℃; for 2h; Addition;	92%

1-acetylimidazolidin-2-one (5391-39-9) + 4-amino-5-chloro-2,1,3-benzothiadiazole (30536-19-7) → tizanidine hydrochloride (64461-82-1, 74113-36-3)

Conditions	Yield
Stage #1: 1-acetylimidazolidin-2-one; 4-amino-5-chloro-2,1,3-benzothiadiazole With trichlorophosphate at 60 - 65℃; for 36h; Stage #2: With methanol for 4h; Reflux; Stage #3: With hydrogenchloride In ethanol at 20℃; for 1h;	85%

1-acetylimidazolidin-2-one (5391-39-9) + 5-bromo-2-methyl-1H-indole (1075-34-9) → 5-Bromo-3-(4,5-dihydroimidazol-2-yl)-2-methyl-1H-indole (227801-59-4)

Conditions	Yield
Stage #1: 1-acetylimidazolidin-2-one; 5-bromo-2-methyl-1H-indole With trichlorophosphate at 50℃; Stage #2: With ethanol Heating;	80%
Stage #1: 1-acetylimidazolidin-2-one; 5-bromo-2-methyl-1H-indole With trichlorophosphate at 50℃; Stage #2: With ethanol Heating / reflux;

1-acetylimidazolidin-2-one (5391-39-9) + 5-bromo-2-methyl-1H-indole (1075-34-9) → 5-bromo-3-(4,5-dihydro-1H-imidazol-2-yl)-2-methyl-1H-indole hydrochloride

Conditions	Yield
	80%

1-acetylimidazolidin-2-one (5391-39-9) → C5H6Cl4N2OP(1+)*Cl6P(1-)

Conditions	Yield
With phosphorus pentachloride In chloroform at 20℃; for 24h;	79%

2-chloro-3-aminopyridine (6298-19-7) + 1-acetylimidazolidin-2-one (5391-39-9) → 1-acetyl-2-[3-(2-chloropyridinyl)]iminoimidazolidine

Conditions	Yield
With trichlorophosphate for 3h; Condensation; Heating;	74%

1-acetylimidazolidin-2-one (5391-39-9) + 4-aminoindan (32202-61-2) → N-(1-Acetyl-2-imidazolin-2-yl)-N-(4-indanyl)amin (67356-94-9)

Conditions	Yield
With trichlorophosphate at 50℃; for 40h;	73.1%

5-chloro-2-(2-tolyl)indole + 1-acetylimidazolidin-2-one (5391-39-9) → 5-chloro-3-(4,5-dihydro-1H-imidazol-2-yl)-2-(2-methylphenyl)-1H-indole

Conditions	Yield
	73%
	15.8%

1-acetylimidazolidin-2-one (5391-39-9) + sodium sulfate anhydride + 4-amino-5-chloro-2,1,3-benzothiadiazole (30536-19-7) → tizanidine (51322-75-9)

Conditions	Yield
With trichlorophosphate In methanol; sodium hydroxide; water	73%

1-acetylimidazolidin-2-one (5391-39-9) + 2-(4-methylphenyl)-5-trifluoromethoxy-1H-indole (227803-32-9) → 3-(4,5-dihydroimidazol-2-yl)-2-(4-methylphenyl)-5-trifluoromethoxy-1H-indole hydrochloride

Conditions	Yield
Stage #1: 1-acetylimidazolidin-2-one; 2-(4-methylphenyl)-5-trifluoromethoxy-1H-indole With trichlorophosphate at 60℃; for 20h; Stage #2: In ethanol at 60℃; for 5h;	70%

1-acetylimidazolidin-2-one (5391-39-9) + 4-amino-5-chloro-2,1,3-benzothiadiazole (30536-19-7) → tizanidine (51322-75-9)

Conditions	Yield
Stage #1: 1-acetylimidazolidin-2-one; 4-amino-5-chloro-2,1,3-benzothiadiazole With trichlorophosphate at 60 - 65℃; for 36h; Stage #2: With methanol; sodium hydroxide for 4h; Reflux;	70%

1-acetylimidazolidin-2-one (5391-39-9) + 2,6-diethylaniline (579-66-8) → 1-acetyl-N-(2,6-diethylphenyl)-4,5-dihydro-1H-imidazol-2(3H)-imine (86861-31-6)

Conditions	Yield
With trichlorophosphate for 3h; Heating;	69.9%

5-chloro-2-m-tolyl-1H-indole + 1-acetylimidazolidin-2-one (5391-39-9) → 3-(4,5-dihydro-1H-imidazol-2-yl)-5-chloro-2-(3-methylphenyl)-1H-indole hydrochloride

Conditions	Yield
	68%

1-acetylimidazolidin-2-one (5391-39-9) + 2-(4-methylphenyl)-5-chloro-1H-indole (66866-07-7) → 5-Chloro-3-(4,5-dihydroimidazol-2-yl)-2-(4-methylphenyl)-1H-indole

Conditions	Yield
Stage #1: 1-acetylimidazolidin-2-one; 2-(4-methylphenyl)-5-chloro-1H-indole With trichlorophosphate at 50℃; Stage #2: With ethanol Heating;	67%

1-acetylimidazolidin-2-one (5391-39-9) + 2-ethyl-5-chloro-1H-indole (366448-75-1) → 5-chloro-3-(4,5-dihydro-1-H-imidazol-2-yl)-2-ethyl-1H-indole

Conditions	Yield
Stage #1: 1-acetylimidazolidin-2-one; 2-ethyl-5-chloro-1H-indole With trichlorophosphate at 50℃; Stage #2: With ethanol Heating;	67%
	7.1%

1-acetylimidazolidin-2-one (5391-39-9) + 4-(4-(chloromethyl)phenyl)-2-(2,6-difluorophenyl)-4,5-dihydrooxazole → 1-acetyl-3-(4-(2-(2,6-difluorophenyl)-4,5-dihydrooxazol-4-yl)benzyl)imidazolidin-2-one

Conditions	Yield
With tetrabutylammomium bromide; sodium hydroxide In toluene at 20℃; for 5h;	67%

1-acetylimidazolidin-2-one (5391-39-9) + 4-chloro-2-methyl-1H-indole (6127-16-8) → 4-chloro-3-(4,5-dihydro-1H-imidazol-2-yl)-2-methyl-1H-indole hydrochloride

Conditions	Yield
	66%

C14H9Cl2N + 1-acetylimidazolidin-2-one (5391-39-9) → 3-(4,5-dihydro-1H-imidazol-2-yl)-5-chloro-2-(2-chlorophenyl)-1H-indole hydrochloride

Conditions	Yield
	66%

1-acetylimidazolidin-2-one (5391-39-9) + 3-amino-2-methylchromone hydrochloride → 1-acetyl-2-(2-methyl-4-oxo-4H-benzopyran-3-yl)iminoimidazolidine

Conditions	Yield
With trichlorophosphate Condensation;	65%

C15H11Cl2N + 1-acetylimidazolidin-2-one (5391-39-9) → 3-(4,5-dihydro-1H-imidazol-2-yl)-5-chloro-2-(3-methyl-4-chlorophenyl)-1H-indole hydrochloride

Conditions	Yield
	65%

2-(4-methoxyphenyl)-5-chloro-1H-indole + 1-acetylimidazolidin-2-one (5391-39-9) → 5-chloro-3-(4,5-dihydro-1H-imidazol-2-yl)-2-(4-methoxyphenyl)-1H-indole hydrochloride

Conditions	Yield
	64.8%
	45%

1-acetylimidazolidin-2-one (5391-39-9) + 5-methoxy-2-methyl-1H-indole (1076-74-0) → 5-methoxy-2-methyl-3-(4,5-dihydro-1H-imidazol-2-yl)-1H-indole

Conditions	Yield
Stage #1: 1-acetylimidazolidin-2-one; 5-methoxy-2-methyl-1H-indole With trichlorophosphate at 50℃; Stage #2: With ethanol Heating;	64%
	14.6%

1-acetylimidazolidin-2-one (5391-39-9) + diisopropyl hydrogenphosphonate (1809-20-7) → diisopropyl(3-acetyl-2-oxoimidazolidin-1-yl)phosphonate (1417780-53-0)

Conditions	Yield
With 6,6'-dimethyl-2,2'-bipyridine; copper diacetate In toluene at 80℃; under 760.051 Torr; for 1.5h; Reagent/catalyst; Molecular sieve;	64%

1-acetylimidazolidin-2-one (5391-39-9) + 2-phenyl-indole (948-65-2) → 2-phenyl-3-(4,5-dihydro-1H-imidazol-2-yl)-1H-indole hydrochloride

Conditions	Yield
	63.9%

Upstream product

• 120-93-4 imidazolidone 
• 108-24-7 acetic anhydride 
• 1001-53-2 monoacetylaminoethylamine 
• 124-38-9 carbon dioxide 
• 18773-93-8 1-acetyl-1H-benzotriazole 
• 65118-65-2 imidazol-2-one 
• 75-36-5 acetyl chloride 
• 88333-03-3 Benzyl isocyanide 

Downstream Products

• 86861-31-6 1-acetyl-N-(2,6-diethylphenyl)-4,5-dihydro-1H-imidazol-2(3H)-imine 
• 67356-94-9 N-(1-Acetyl-2-imidazolin-2-yl)-N-(4-indanyl)amin 
• 120712-01-8 1-acetyl-2-<(4-benzyl-3,4-dihydro-1,4-benzoxazin-7-yl)imino>imidazolidine 
• 39958-49-1 1,3-di-(1-methyl-5-nitroimidazolyl-2)-tetrahydroimidazole 
• 39958-48-0 1-(1-methyl-5-nitro-imidazolyl-2)-3-acetyl-2-oxo-tetrahydroimidazole 
• 41730-71-6 1-chlorocarbonyl-2-oxo-3-methylcarbonyl-imidazolidine 
• 320778-06-1 1-acetyl-4-methoxy-imidazolidin-2-one 
• 4751-48-8 2-(2,6-diethylphenylimino)imidazolidine 
• 4749-51-3 (4,5-dihydro-1H-imidazol-2-yl)-(2-ethyl-phenyl)-amine 
• 59772-30-4 2-(2-Ethyl-6-methylphenylimino)-imidazolidin 
• 63346-74-7 (4,5-dihydro-1H-imidazol-2-yl)-(2,6-diisopropyl-phenyl)-amine 
• 4859-06-7 2-(2,6-dimethylphenylimino)imidazolidine 
• 4201-40-5 (4,5-dihydro-1H-imidazol-2-yl)-(2,4,6-trimethyl-phenyl)-amine 
• 36318-56-6 (4,5-dihydro-1H-imidazol-2-yl)-o-tolyl-amine 

Relevant articles and documents

N-VINYLIMIDAZOLIDONE COMPOUND, AND POLYMER THEREOF

PROBLEM TO BE SOLVED: To provide an N-vinylimidazolidone compound polymer that is expected to be applied for a cell culture material, a temperature-responsive material and others. SOLUTION: The present invention provides a polymer polymerized with an N-vinylimidazolidone compound (1) as a monomer, or a copolymer comprising the monomer and a monomer of a different structure (R1 is H, C1-12 alkyl or acyl; R2 and R3 is H or methyl). SELECTED DRAWING: None COPYRIGHT: (C)2016,JPOandINPIT

CO2-Fixation on Aliphatic α,ω-Diamines to Form Cyclic Ureas, Catalyzed by Ceria Nanoparticles that were Obtained by Templating with Alginate

Ceria nanoparticles (average particle size: 8nm) have been obtained by the calcination of alginate aerogel beads that were precipitated from aqueous solutions of (NH4)2Ce(NO3)6. These nanoparticles were considerably more active as a catalyst for CO2-insertion into aliphatic α,ω-diamines than the analogous commercial CeO2 with larger particle size (40nm). CeO2 that was obtained by templating with the natural alginate biopolymer afforded the cyclic urea of ethylenediamine in EtOH solvent at 160°C in 37% yield. This yield is remarkable for a process that involves CO2 as a feedstock. Other α,ω-diamines, such as diethylenetriamine, N,N′-dimethylethylenediamine, N-(2-aminoethyl)acetamide, and 1,4-diaminobutane, also formed their corresponding cyclic ureas in 4-36% yield. The catalyst lost activity upon reuse, thereby leading to severe deactivation that was only partially recovered by washing with aqueous acidic solutions.

First practical synthesis of formamidine ureas and derivatives

(Matrix presented) Isonitriles and ureas undergo a condensation reaction in the presence of acid chlorides to give formamidine ureas, for which no general synthetic routes currently exist. A mechanism is proposed in which the key intermediate is an electrophilic adduct of isonitrile and acid chloride. The process is tolerant of moderate variability in the nature of the components, and access to formamidine ureas of varying substitution patterns is further enhanced by a facile exchange reaction with amines.