5918-93-4

Basic information

• Product Name: 1,3-Dihydroimidazol-2-one
• Synonyms: 1,3-dihydro-2h-imidazol-2-on;1,3-dihydro-2h-imidazol-2-one;2-hydroxyimidazole;4-imidazolin-2-one;ent-27439;sd8591;shellsd-8591;2,3-DIHYDRO-IMIDAZOL-2-ONE
• CAS NO: 5918-93-4
• Molecular Formula: C₃H₄N₂O
• Molecular Weight: 84.08
• EINECS: 1312995-182-4
• Product Categories: API intermediates
• Mol File: 5918-93-4.mol
• Article Data: 13

Chemical Properties

• Melting Point: 240-243 °C
• Boiling Point: 364.5 °C at 760 mmHg
• Flash Point: 174.3 °C
• Appearance: /
• Density: 1.191 g/cm³
• Vapor Pressure: 7.97E-06mmHg at 25°C
• Refractive Index: 1.486
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 12.20±0.70(Predicted)
• CAS DataBase Reference: 1,3-Dihydroimidazol-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3-Dihydroimidazol-2-one(5918-93-4)
• EPA Substance Registry System: 1,3-Dihydroimidazol-2-one(5918-93-4)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• Hazardous Substances Data: 5918-93-4(Hazardous Substances Data)

Usage

Uses

1,3-Dihydroimidazol-2-one is used as a reagent in the synthesis of a series of hydantoins (H675000), triazolones, and imidazolones as non-hydroxamate tumor necrosis factor-α converting enzyme (TACE) inhibitors.

InChI:InChI=1/C3H4N2O/c6-3-4-1-2-5-3/h1-2H,(H2,4,5,6)

Synthetic route

2,4-imidazolidinedione (461-72-3) → 1,3-dihydroimidazolone (5918-93-4)

Conditions	Yield
Stage #1: 2,4-imidazolidinedione With diisobutylaluminium hydride In tetrahydrofuran at 0℃; for 7.41667h; Inert atmosphere; Stage #2: With water In methanol for 13.5h; Reflux; Inert atmosphere;	93%
Stage #1: 2,4-imidazolidinedione With diisobutylaluminium hydride In tetrahydrofuran; toluene at 0℃; for 2.5h; Inert atmosphere; Stage #2: With water In tetrahydrofuran; methanol; toluene at 100℃; for 18h; Inert atmosphere;	83%
Stage #1: 2,4-imidazolidinedione With diisobutylaluminium hydride In tetrahydrofuran; toluene at 0℃; for 2h; Stage #2: With methanol Heating; Further stages.;	62%
With diisobutylaluminium hydride In tetrahydrofuran; toluene at 0℃; for 1.5h;	1.4 g

2-oxo-4-imidazoline-4-carboxylic acid (39828-47-2) → 1,3-dihydroimidazolone (5918-93-4)

Conditions	Yield
With potassium carbonate for 4h; Heating;	75%
at 220℃; under 2 Torr;
at 230 - 240℃; under 5 Torr;
With copper at 230 - 300℃; under 0.3 Torr;

α-ureidoacetaldehyde diethyl acetal (80049-53-2) → 1,3-dihydroimidazolone (5918-93-4)

Conditions	Yield
With sulfuric acid at 25℃; for 48h;	53%
With sulfuric acid In water at 55℃; for 1h;	44%
With sulfuric acid In water at 20 - 55℃; for 3h; Inert atmosphere;	44%
With sulfuric acid

1-Benzyloxy-1,3-dihydro-imidazol-2-one (116451-56-0) → 1,3-dihydroimidazolone (5918-93-4)

Conditions	Yield
With sodium hydroxide In methanol at 20℃; for 3h;	51%

glycine ethyl ester hydrochloride (623-33-6) → 1,3-dihydroimidazolone (5918-93-4)

Conditions	Yield
With hydrogenchloride; sodium amalgam Anschliessend mit Kaliumcyanat bei pH 7 behandeln;

1-vinyloxycarbonylimidazol-2-one (343864-63-1) → 1,3-dihydroimidazolone (5918-93-4)

Conditions	Yield
for 1h; Heating;

urea (57-13-6) + anhydrous dioxylmaleic acid → 1,3-dihydroimidazolone (5918-93-4)

C13H15ClN2O2Zr → 1,3-dihydroimidazolone (5918-93-4)

Conditions	Yield
With water In tetrahydrofuran at 20℃; for 0.166667h; Inert atmosphere;

1,3-dihydroimidazolone (5918-93-4) + acetic anhydride (108-24-7) → 1,3-diacetyl-2,3-dihydro-1H-imidazol-2-one (20212-13-9)

Conditions	Yield
for 1.5h; Reflux;	99.5%
for 1.5h; Reflux;	95%
Heating;	80%

1,3-dihydroimidazolone (5918-93-4) + acetyl chloride (75-36-5) → 1-H-5-acetyl-2-imidazolone (92635-44-4)

Conditions	Yield
With aluminium trichloride In nitrobenzene at 60 - 65℃;	93%

1,3-dihydroimidazolone (5918-93-4) + 3-iodobenzylalcohol (57455-06-8) → 4-(3-(hydroxymethyl)phenyl)-1H-imidazol-2(3H)-one

Conditions	Yield
With sodium acetate; palladium diacetate In dimethyl sulfoxide at 80℃; for 6h;	87%

1,3-dihydroimidazolone (5918-93-4) + para-iodoanisole (696-62-8) → 4-(4-methoxyphenyl)-1H-imidazol-2(3H)-one (6794-72-5)

Conditions	Yield
With sodium acetate; palladium diacetate In dimethyl sulfoxide at 80℃; for 6h;	85%

1,3-dihydroimidazolone (5918-93-4) + 4-Iodophenol (540-38-5) → 4-(4-hydroxyphenyl)-1H-imidazol-2(3H)-one

Conditions	Yield
With sodium acetate; palladium diacetate In dimethyl sulfoxide at 80℃; for 6h;	85%

1,3-dihydroimidazolone (5918-93-4) + 1,1,1,3,3,3-hexamethyl-disilazane (999-97-3) → 1-(trimethylsilyl)-2-<(trimethylsilyl)oxy>imidazole (80049-39-4)

Conditions	Yield
With pyridine; chloro-trimethyl-silane for 7h; Heating;	78%

1,3-dihydroimidazolone (5918-93-4) + iodobenzene (591-50-4) → 4-phenyl-1,3-dihydro-imidazol-2-one (6794-69-0)

Conditions	Yield
With sodium acetate; palladium diacetate In dimethyl sulfoxide at 80℃; for 6h;	78%

1,3-dihydroimidazolone (5918-93-4) + 3-methoxy-1-iodobenzene (766-85-8) → 4-(3-methoxyphenyl)-1H-imidazol-2(3H)-one

Conditions	Yield
With sodium acetate; palladium diacetate In dimethyl sulfoxide at 80℃; for 6h;	77%

1,3-dihydroimidazolone (5918-93-4) + di-tert-butyl dicarbonate (24424-99-5) → di-tert-butyl 2-oxo-1H-imidazole-1,3(2H)-dicarboxylate

Conditions	Yield
With dmap In acetonitrile at 0℃; for 2h; Inert atmosphere;	77%

1,3-dihydroimidazolone (5918-93-4) + pivaloyl chloride (3282-30-2) → 1,1'-(2-oxo-1H-imidazole-1,3(2H)-diyl)bis(2,2-dimethylpropan-1-one)

Conditions	Yield
With dmap; triethylamine In dichloromethane at 0℃; for 24h; Inert atmosphere;	77%

1,3-dihydroimidazolone (5918-93-4) + 4-phenyl-semicarbazide (537-47-3) → C10H11N5O (1380571-17-4)

Conditions	Yield
With acetic acid In ethanol Microwave irradiation;	76%

1,3-dihydroimidazolone (5918-93-4) + ortho-methylphenyl iodide (615-37-2) → 4-(2-methylphenyl)-1H-imidazol-2(3H)-one

Conditions	Yield
With sodium acetate; palladium diacetate In dimethyl sulfoxide at 80℃; for 6h;	75%

1,3-dihydroimidazolone (5918-93-4) + benzoyl chloride (98-88-4) → (2-oxo-1H-imidazole-1,3(2H)-diyl)bis(phenylmethanone)

Conditions	Yield
With dmap; triethylamine In dichloromethane at 0 - 20℃; for 25h; Inert atmosphere;	73%
With dmap; triethylamine In dichloromethane at 0℃; for 24h; Inert atmosphere;	44%

1,3-dihydroimidazolone (5918-93-4) + [(E)-2-bromoethenyl]benzene (588-72-7) → (E)-4-styryl-1H-imidazol-2(3H)-one

Conditions	Yield
With sodium acetate; palladium diacetate In dimethyl sulfoxide at 80℃; for 36h;	68%

1,3-dihydroimidazolone (5918-93-4) + 2-nitrophenyl bromide (577-19-5) → 4-(2-nitrophenyl)-1H-imidazol-2(3H)-one

Conditions	Yield
With sodium acetate; palladium diacetate In dimethyl sulfoxide at 80℃; for 24h;	68%

1,3-dihydroimidazolone (5918-93-4) + 4-tolyl iodide (624-31-7) → 1,3-di-p-tolylimidazolin-2-one

Conditions	Yield
With potassium phosphate; (S,S)-1,2-diaminocyclohexane; copper(l) iodide In 1,4-dioxane at 120℃; for 15h;	67%

1,3-dihydroimidazolone (5918-93-4) + 3,4,5-trifluorobenzene-1-sulfonyl chloride (351003-43-5) → 1,3-bis((3,4,5-trifluorophenyl)sulfonyl)-1,3-dihydro-2H-imidazol-2-one

Conditions	Yield
Stage #1: 1,3-dihydroimidazolone With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0 - 20℃; for 0.5h; Inert atmosphere; Stage #2: 3,4,5-trifluorobenzene-1-sulfonyl chloride In N,N-dimethyl-formamide; mineral oil at 0 - 20℃; for 12h; Inert atmosphere;	65%

1,3-dihydroimidazolone (5918-93-4) + p-trifluoromethylphenyl bromide (402-43-7) → 4-(4-(trifluoromethyl)phenyl)-1H-imidazol-2(3H)-one (944916-43-2)

Conditions	Yield
With sodium acetate; palladium diacetate In dimethyl sulfoxide at 80℃; for 36h;	64%

1,3-dihydroimidazolone (5918-93-4) + 2-iodobenzyl alcohol (5159-41-1) → 4-(2-(hydroxymethyl)phenyl)-1H-imidazol-2(3H)-one

Conditions	Yield
With sodium acetate; palladium diacetate In dimethyl sulfoxide at 80℃; for 6h;	62%

1,3-dihydroimidazolone (5918-93-4) + 1-(3-Bromophenyl)ethanone (2142-63-4) → 4-(3-acetylphenyl)-1H-imidazol-2(3H)-one

Conditions	Yield
With sodium acetate; palladium diacetate In dimethyl sulfoxide at 80℃; for 36h;	62%

1,3-dihydroimidazolone (5918-93-4) + 4-fluoro-1-iodobenzene (352-34-1) → 4-(4-fluorophenyl)-1H-imidazol-2(3H)-one

Conditions	Yield
With sodium acetate; palladium diacetate In dimethyl sulfoxide at 80℃; for 12h;	62%

1,3-dihydroimidazolone (5918-93-4) + 4-(methylthio)benzoyl chloride (1442-06-4) → 4-(4-Methylsulfanyl-benzoyl)-1,3-dihydro-imidazol-2-one (83167-14-0)

Conditions	Yield
With aluminium trichloride In nitrobenzene at 60 - 65℃; for 6h;	61%

1,3-dihydroimidazolone (5918-93-4) + 1-Chloro-4-iodobenzene (637-87-6) → 4-(4-chlorophenyl)-1H-imidazol-2(3H)-one (142230-57-7)

Conditions	Yield
With sodium acetate; palladium diacetate In dimethyl sulfoxide at 80℃; for 12h;	61%

1,3-dihydroimidazolone (5918-93-4) + 2-bromo-pyridine (109-04-6) → 1,3-di(pyrid-2'-yl)imidazolin-2-one

Conditions	Yield
With 1,10-Phenanthroline; caesium carbonate; copper(I) trifluoromethanesulfonate benzene In 1,4-dioxane at 120℃; for 15h;	61%

1,3-dihydroimidazolone (5918-93-4) + 3,4-difluorobenzenesulfonyl chloride (145758-05-0) → 1,3-bis((3,4-difluorophenyl)sulfonyl)-1,3-dihydro-2H-imidazol-2-one

Conditions	Yield
Stage #1: 1,3-dihydroimidazolone With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0 - 20℃; for 0.5h; Inert atmosphere; Stage #2: 3,4-difluorobenzenesulfonyl chloride In N,N-dimethyl-formamide; mineral oil at 0 - 20℃; for 12h; Inert atmosphere;	61%

1,3-dihydroimidazolone (5918-93-4) + 2-Thiophenecarbonyl chloride (5271-67-0) → 1,3-dihydro-4-(2-thienoyl)-2H-imidazol-2-one (77681-44-8)

Conditions	Yield
With aluminium trichloride In nitrobenzene at 60 - 65℃; for 6h;	60%
aluminium trichloride In nitrobenzene

1,3-dihydroimidazolone (5918-93-4) + ethyl chlorocarbonylacetate (36239-09-5) → 3-Oxo-3-(2-oxo-2,3-dihydro-1H-imidazol-4-yl)-propionic acid ethyl ester (107097-35-8)

Conditions	Yield
With tin(IV) chloride In nitromethane	60%

1,3-dihydroimidazolone (5918-93-4) + p-toluenesulfonyl chloride (98-59-9) → 1,3-ditosyl-1,3-dihydro-2H-imidazol-2-one

Conditions	Yield
Stage #1: 1,3-dihydroimidazolone With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0 - 20℃; for 0.5h; Inert atmosphere; Stage #2: p-toluenesulfonyl chloride In N,N-dimethyl-formamide; mineral oil at 0 - 20℃; for 12h; Reagent/catalyst; Solvent; Inert atmosphere;	59%

Upstream product

• 39828-47-2 2-oxo-4-imidazoline-4-carboxylic acid 
• 57-13-6 urea 
• 116451-56-0 1-Benzyloxy-1,3-dihydro-imidazol-2-one 
• 343864-63-1 1-vinyloxycarbonylimidazol-2-one 
• 461-72-3 2,4-imidazolidinedione 
• 623-33-6 glycine ethyl ester hydrochloride 
• 80049-53-2 α-ureidoacetaldehyde diethyl acetal 

Downstream Products

• 142551-19-7 1,3-divinyl-1,3-dihydro-2H-imidazol-2-one 

Relevant articles and documents

CYCLOADDITION REACTIONS OF 1,3-DIACETYLIMIDAZOLIN-2-ONE

1,3-Diacetylimidazolin-2-one, for wich a new preparation is described, has been found to undergo thermal cycloaddition reactions with a limited number of dienes; in contrast it undergoes photochemical cycloadditions quite readily.

Stabilization of radicals by imides. A modular stereoselective approach to protected functional 1,2-diamines

(Chemical Equation Presented) Radical addition of various xanthates to N,N′-diacylimidazol-2-one occurs readily to give protected 1,2-diamines. The imide group stabilizes the adduct radical sufficiently to enable a second addition to unactivated alkenes. In some cases, the addition product could be converted into an indoline, a tetralone, or further added to an indole. Regioselective removal of one acyl group could also be accomplished.

Lewis Acid Catalyzed Enantioselective Desymmetrization of Donor–Acceptor meso-Diaminocyclopropanes

The first Lewis acid catalyzed enantioselective ring-opening desymmetrization of a donor–acceptor meso-diaminocyclopropane is reported. The copper(II)-catalyzed Friedel–Crafts alkylation of indoles and one pyrrole with an unprecedented meso-diaminocyclopropane delivered enantioenriched, diastereomerically pure urea products, which are structurally related to natural and synthetic bioactive compounds. The development of a new ligand through the investigation of an underexplored subclass of bis(oxazoline) ligands was essential for achieving high enantioselectivities.

Synthesis of N-heterocyclic compounds via ene-yne metathesis reactions

Propargylamino and allylamino derivatives of cyclohexene and norbornene were subjected to tandem metathesis reactions with first and second generation Grubbs' catalysts 1 and 2. Results show that the method is compatible with suitably protected nitrogen-containing compounds. Cyclohexenes gave intriguing results in terms of the possibility to perform ring rearrangement metathesis (RRM) reactions, showing a difference with the analogous allyl and propargyl ether substrates.