3923-79-3

Usage

Flammability and Explosibility

Nonflammable

InChI:InChI=1/C5H10N2O3/c1-6-3(8)4(9)7(2)5(6)10/h3-4,8-9H,1-2H3

Synthetic route

1,1-Dimethylurea (598-94-7) → 4,5-dihydroxy-1,3-dimethylimidazolidin-2-one (3923-79-3)

Conditions	Yield
In methanol	83%

Glyoxal (131543-46-9) + N,N'-Dimethylurea (96-31-1) → 4,5-dihydroxy-1,3-dimethylimidazolidin-2-one (3923-79-3)

Conditions	Yield
With hydrogenchloride In water at 60℃; for 4h; pH=3;
With triethylamine In water at 25 - 35℃; pH=9;
In water at 50℃; for 4h; pH=4;
With triethylamine In water at 25 - 35℃; for 16h;

4,5-dihydroxy-1,3-dimethylimidazolidin-2-one (3923-79-3) → 1,3-dimethylimidazolidine-2,4-dione (24039-08-5)

Conditions	Yield
sulfuric acid In 1,3-dimethyl-2-imidazolidinone at 150℃; for 2h; Product distribution / selectivity;	100%
In water at 80 - 90℃; pH=1;
With sodium hydrogencarbonate In water at 60℃; for 4h;	115 mg
With sulfuric acid In water at 95 - 100℃; for 6h;	161 g

thiosemicarbazide (79-19-6) + 4,5-dihydroxy-1,3-dimethylimidazolidin-2-one (3923-79-3) → 5,7-dimethyl-3-thioxoperhydroimidazo[4,5-e]-1,2,4-triazin-6-one + 1,3-dimethylimidazolidine-2,4-dione (24039-08-5)

Conditions	Yield
With hydrogenchloride In methanol at 80℃; for 1h;	A 96% B n/a

thiosemicarbazide (79-19-6) + 4,5-dihydroxy-1,3-dimethylimidazolidin-2-one (3923-79-3) → (4aRS,7aSR)-5,7-dimethyl-3-thioxooctahydroimidazo[4,5-e]-1,2,4-triazin-6-one

Conditions	Yield
With hydrogenchloride In methanol for 0.5h; Heating;	94%

N'-cyclohexylurea (698-90-8) + 4,5-dihydroxy-1,3-dimethylimidazolidin-2-one (3923-79-3) → 4,5-bis(3-cyclohexylureido)-1,3-dimethyl-imidazolidin-2-one

Conditions	Yield
With hydrogenchloride at 80℃; for 1h; pH=1;	92%

p-toluene sulfinic acid (536-57-2) + 4,5-dihydroxy-1,3-dimethylimidazolidin-2-one (3923-79-3) → trans-4-hydroxy-1,3-dimethyl-5-(p-tolylsulfonyl)-2-imidazolidinone

Conditions	Yield
In water Ambient temperature;	90.5%

thiosemicarbazide (79-19-6) + 4,5-dihydroxy-1,3-dimethylimidazolidin-2-one (3923-79-3) → 1,3-dimethyl-4,5-bis(3-thiosemicarbazido)imidazolidin-2-one + 1,3-dimethylimidazolidine-2,4-dione (24039-08-5)

Conditions	Yield
With hydrogenchloride In water at 80℃; for 1h; pH=2;	A 90% B n/a

p-toluene sulfinic acid (536-57-2) + 4,5-dihydroxy-1,3-dimethylimidazolidin-2-one (3923-79-3) → 1,3-dimethyl-4-(p-tolylsulfonyl)-2-imidazolinone

Conditions	Yield
In water for 0.5h; Heating;	88.6%

toluene-4-sulfonamide (70-55-3) + 4,5-dihydroxy-1,3-dimethylimidazolidin-2-one (3923-79-3) → N-[1,3-Dimethyl-2-oxo-imidazolidin-(4E)-ylidene]-4-methyl-benzenesulfonamide

Conditions	Yield
With hydrogenchloride In methanol at 60 - 70℃; for 0.5h;	83%

benzenesulfonamide (98-10-2) + 4,5-dihydroxy-1,3-dimethylimidazolidin-2-one (3923-79-3) → N-[1,3-Dimethyl-2-oxo-imidazolidin-(4E)-ylidene]-benzenesulfonamide

Conditions	Yield
With hydrogenchloride In methanol at 60 - 70℃; for 0.5h;	82%

(S)-1-sec-butyl-3-methylurea (1404101-01-4) + 4,5-dihydroxy-1,3-dimethylimidazolidin-2-one (3923-79-3) → (S)-(+)-2-sec-butyl-4,6,8-trimethylglycoluril (1404101-10-5)

Conditions	Yield
With hydrogenchloride In water; isopropyl alcohol for 2h; Reflux;	80%

(R)-1-sec-butyl-3-methylurea (1404101-02-5) + 4,5-dihydroxy-1,3-dimethylimidazolidin-2-one (3923-79-3) → (R)-(-)-2-sec-butyl-4,6,8-trimethylglycoluril (1404101-11-6)

Conditions	Yield
With hydrogenchloride In water; isopropyl alcohol for 2h; Reflux;	80%

1-aminoguanidine hydrochloride (1937-19-5) + 4,5-dihydroxy-1,3-dimethylimidazolidin-2-one (3923-79-3) → 4-(guanidinoimino)-1,3-dimethylimidazolidin-2-one hydrochloride

Conditions	Yield
Stage #1: 4,5-dihydroxy-1,3-dimethylimidazolidin-2-one With hydrogenchloride In methanol at 60℃; Stage #2: 1-aminoguanidine hydrochloride In methanol at 70 - 75℃; for 1h;	78%

1,1-dimethylethylurea (1118-12-3) + 4,5-dihydroxy-1,3-dimethylimidazolidin-2-one (3923-79-3) → C10H18N4O2 + 4,5-bis(3-tert-butylureido)-1,3-dimethyl-imidazolidin-2-one + 1,3-dimethylimidazolidine-2,4-dione (24039-08-5)

Conditions	Yield
With hydrogenchloride at 80℃; for 1h; pH=1;	A 77% B 10% C n/a

4,5-dihydroxy-1,3-dimethylimidazolidin-2-one (3923-79-3) + 1-cyclohexyl-3-methylurea (39804-96-1) → 8-cyclohexyl-2,4,6-trimethyl-2,4,6,8-tetraazabicyclo[3.3.0]octane-3,7-dione

Conditions	Yield
With hydrogenchloride In water for 1h; Heating;	72%

1-(pyrimidin-2-yl)urea (33561-08-9) + 4,5-dihydroxy-1,3-dimethylimidazolidin-2-one (3923-79-3) → 1,3-dimethyl-4,5-bis[3-(2-pyrimidinyl)ureido]imidazolidin-2-one

Conditions	Yield
With hydrogenchloride at 80℃; for 1h; pH=1;	70%

4,5-dihydroxy-1,3-dimethylimidazolidin-2-one (3923-79-3) → trans-4,5-diazido-1,3-dimethylimidazolidin-2-one

Conditions	Yield
With hydrogenchloride; sodium azide for 120h;	67%

N-tert-Butyl-N'-methylharnstoff (25347-94-8) + 4,5-dihydroxy-1,3-dimethylimidazolidin-2-one (3923-79-3) → 2-tert-butyl-4,6,8-trimethyl-2,4,6,8-tetraazabicyclo[3.3.0]octane-3,7-dione (71540-86-8)

Conditions	Yield
With hydrogenchloride In water for 1h; Heating;	65%

thiosemicarbazide (79-19-6) + 4,5-dihydroxy-1,3-dimethylimidazolidin-2-one (3923-79-3) → 5,7-dimethyl-3-thioxoperhydroimidazo[4,5-e]-1,2,4-triazin-6-one + 1,3-dimethyl-4,5-bis(3-thiosemicarbazido)imidazolidin-2-one

Conditions	Yield
With hydrogenchloride In ethanol; water at 50℃; for 1.2h; Reflux;	A 65% B 17%

1-[(2E,6E,10E)-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraenyl]-3-methylurea + 4,5-dihydroxy-1,3-dimethylimidazolidin-2-one (3923-79-3) → 2-[(2E,6E,10E)-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraenyl]-4,6,8-trimethyl-2,4,6,8-tetraazabicyclo[3.3.0]octane-3,7-dione

Conditions	Yield
With hydrogenchloride In water for 1h; Heating;	61%

N,N'-diethylurea (623-76-7) + 4,5-dihydroxy-1,3-dimethylimidazolidin-2-one (3923-79-3) → 1,3-dimethyl-4,6-diethyl-tetrahydroimidazo[4,5-d]imidazole-2,5(1H,3H)-dione

Conditions	Yield
Heating;	60%

N-methyl-N'-propylurea (38014-52-7) + 4,5-dihydroxy-1,3-dimethylimidazolidin-2-one (3923-79-3) → 2,4,6-trimethyl-8-propyl-2,4,6,8-tetraazabicyclo[3.3.0]octane-3,7-dione

Conditions	Yield
With hydrogenchloride In water for 1h; Heating;	59%

1-aminoguanidine hydrochloride (1937-19-5) + 4,5-dihydroxy-1,3-dimethylimidazolidin-2-one (3923-79-3) → 1,3-dimethyl-4,5-bis(3-guanidinioamino)imidazolidin-2-one dihydrochloride

Conditions	Yield
Stage #1: 4,5-dihydroxy-1,3-dimethylimidazolidin-2-one With hydrogenchloride In water at 80℃; Stage #2: 1-aminoguanidine hydrochloride In water at 80℃; for 1h;	57%
With hydrogenchloride In methanol at 70 - 75℃; for 1h;

N-carbamoylglycine (462-60-2) + 4,5-dihydroxy-1,3-dimethylimidazolidin-2-one (3923-79-3) → rac-(1S,5S)-(6,8-dimethyl-3,7-dioxo-2,4,6,8-tetraazabicyclo[3.3.0]octan-2-yl)acetic acid

Conditions	Yield
With hydrogenchloride In water at 85℃; for 2h; pH=3;	55%
With hydrogenchloride In water at 85℃; for 3h; pH=1;

Benzenesulfinic acid (618-41-7) + 4,5-dihydroxy-1,3-dimethylimidazolidin-2-one (3923-79-3) → 1,3-dimethyl-4-phenylsulfonyl-2-imidazolinone

Conditions	Yield
In water Heating;	53.5%

N,N'-dimethylsulfamide (22504-72-9) + 4,5-dihydroxy-1,3-dimethylimidazolidin-2-one (3923-79-3) → 2,4,6,8-tetramethyl-3-thia-2,4,6,8-tetraazabicyclo[3.3.0]octan-7-one 3,3-dioxide

Conditions	Yield
With hydrogenchloride at 80 - 90℃; for 1h; pH=1;	53%

imidazolidone (120-93-4) + 4,5-dihydroxy-1,3-dimethylimidazolidin-2-one (3923-79-3) → 1,3-dimethyl-4,5-bis(2-oxoimidazolidin-1-yl)imidazolidin-2-one + 1,3-dimethylimidazolidine-2,4-dione (24039-08-5)

Conditions	Yield
With hydrogenchloride In water for 1.5h; pH=1; Heating;	A 53% B n/a
With hydrogenchloride for 1.5h; pH=1 - 2; Heating;	A 53% B n/a

N,N-diethylurea (634-95-7) + 4,5-dihydroxy-1,3-dimethylimidazolidin-2-one (3923-79-3) → 1,3-dimethyl-4,5-bis(3,3-diethyllureido)imidazolidin-2-one + 1,3-dimethylimidazolidine-2,4-dione (24039-08-5)

Conditions	Yield
With hydrogenchloride at 60 - 70℃; for 1h; pH=1;	A 53% B n/a

methanesulfonamide (3144-09-0) + 4,5-dihydroxy-1,3-dimethylimidazolidin-2-one (3923-79-3) → N-[1,3-Dimethyl-2-oxo-imidazolidin-(4E)-ylidene]-methanesulfonamide

Conditions	Yield
With hydrogenchloride In methanol at 60 - 70℃; for 0.5h;	50%

4,5-dihydroxy-1,3-dimethylimidazolidin-2-one (3923-79-3) → 6,8-dimethyl-3-thia-2,4,6,8-tetraazabicyclo[3.3.0]octan-7-one 3,3-dioxide (327040-82-4)

Conditions	Yield
With SULFAMIDE In water at 60℃; for 0.5h; pH=5 - 6;	49%

Upstream product

• 598-94-7 1,1-Dimethylurea 
• 131543-46-9 Glyoxal 
• 96-31-1 N,N'-Dimethylurea 

Downstream Products

• 185011-09-0 1,3-dimethyl-4-phenylsulfonyl-2-imidazolinone 
• 185011-07-8 1,3-dimethyl-4-(p-tolylsulfonyl)-2-imidazolinone 
• 1054463-11-4 C₁₁H₂₀N₄O₃S 
• 504-07-4 5,6-dhydrouracil 
• 24039-08-5 1,3-dimethylimidazolidine-2,4-dione 
• 1242015-42-4 6-(2-(4-hydroxyphenyl)ethyl)-2,4-dimethyl-2,4,6,8-tetraazabicyclo[3.3.0]octane-3,7-dione 
• 1259490-16-8 2-(2-acetylaminoethyl)-6,8-dimethyl-4-phenyl-2,4,6,8-tetraazabicyclo[3.3.0]octane-3,7-dione 
• 1255948-99-2 (E)-4-(benzylideneamino)-1,3-dimethyl-5-thioxohexahydroimidazo[4,5-d]imidazol-2(1H)-one 
• 1418275-10-1 (E)-4-[(2-hydroxybenzylidene)amino]-1,3-dimethyl-5-thioxohexahydroimidazo[4,5-d]imidazol-2(1H)-one 
• 1418275-11-2 (E)-4-(4-fluorobenzylidene)-1,3-dimethyl-5-thioxohexahydroimidazo[4,5-d]imidazol-2(1H)-one 
• 1418275-12-3 (E)-4-[(2-hydroxy-3-methoxybenzylidene)amino]-1,3-dimethyl-5-thioxohexahydroimidazo[4,5-d]imidazol-2(1H)-one 
• 1418275-13-4 (E)-4-[(5-chloro-2-hydroxybenzylidene)amino]-1,3-dimethyl-5-thioxohexahydroimidazo[4,5-d]imidazol-2(1H)-one 
• 1418275-14-5 (E)-4-[(5-bromo-2-hydroxybenzylidene)amino]-1,3-dimethyl-5-thioxohexahydroimidazo[4,5-d]imidazol-2(1H)-one 

Relevant academic research and scientific papers

Hydantoin-based molecular photoswitches

A new family of molecular photoswitches based on arylidenehydantoins is described together with their synthesis and photochemical and photophysical studies. A series of hydantoin derivatives have been prepared as single isomers using simple and versatile chemistry in good yields. Our studies show that the photostationary states of these compounds can be easily controlled by means of external factors, such as the light source or filters. Moreover, the detailed investigations proved that these switches are efficient (i.e., they make efficient use of the light energy, are high fatigue resistant, and are very photostable). In some cases, the switches can be completely turned on/off, a desirable feature for specific applications. A series of theoretical calculations have also been carried out to understand the photoisomerization mechanism at the molecular level.

Dehydrogenation, oxidative denitration and ring contraction of N,N-dimethyl-5-nitrouracil by a Bacillus nitroreductase Nfr-A1

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PROCESS FOR PREPARING IMIDAZOLIDIN-2,4-DIONE COMPOUND AND METHOD FOR ACQUIRING SOLID STATE 4,5-DIHYDROXY-2-IMIDAZOLIDINONE COMPOUND

An object of the present invention is to provide an industrially suitable process for preparing an imidazolidin-2,4-dione compound which is safe, simple and easy to prepare the imidazolidin-2,4-dione compound with high yield, which is a useful compound, for example, as a material for decomposing a harmful halogenated aromatic hydrocarbon compound such as dioxin, etc., an electroless silver plating solution for electronic parts, or a diazo copying material, etc. This object can be solved by a process for preparing an imidazolidin-2,4-dione compound which comprises subjecting a 4,5-dihydroxy-2-imidazolidinone compound, (1) to dehydration reaction in the presence of an acid catalyst(s); or (2) to reaction at 100 to 300° C. Or, it can be solved by a process for preparing an imidazolidin-2,4-dione compound which comprises reacting a mixed solution of a urea compound, glyoxal, and a base at 20 to 300° C. Also, an object of the present invention is to provide a method for acquiring a 4,5-dihydroxy-2-imidazolidinone from an aqueous solution containing a 4,5-dihydroxy-2-imidazolidinone by a simple and easy method. This object can be solved by a process for acquiring a solid state 4,5-dihydroxy-2-imidazolidinone compound which comprises mixing an organic solvent with an aqueous solution containing a 4,5-dihydroxy-2-imidazolidinone compound, and subjecting the mixture to azeotropic distillation.

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.

Preparation of cyclic urea derivatives

Cyclic urea derivatives of the formula I in which X, X', Y, Y' and Z can have various meanings, are prepared by a) reacting a urea derivative of the formula II with a diketone of the formula III and b) hydrogenating the product from step a) in the presence of a metal-containing catalyst.