77-71-4

Basic information

• Product Name: 5,5-Dimethylhydantoin
• Synonyms: 4-Imidazolidinedione,5,5-dimethyl-2;5,5-dimethyl-4-imidazolidinedione;5,5-dimethyl-hydantoi;5,5-Dimethyl-imidazolidin-2,4-dion;5,5-Dimethylimidazolidin-2,4-dione;Acetonylurea;Dantoin DMH;dantoindmh
• CAS NO: 77-71-4
• Molecular Formula: C₅H₈N₂O₂
• Molecular Weight: 128.13
• EINECS: 201-051-3
• Product Categories: Miscellaneous Natural Products;Water treatment chemicals;Building Blocks;Heterocyclic Building Blocks;Imidazolines/Imidazolidines;Resin additives
• Mol File: 77-71-4.mol
• Article Data: 21

Chemical Properties

• Melting Point: 174-177 °C(lit.)
• Boiling Point: 237.54°C (rough estimate)
• Flash Point: 193°C
• Appearance: White to off-white/Crystalline Powder or Crystals
• Density: 1.2864 (rough estimate)
• Refractive Index: 1.4730 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: H2O: 0.1 g/mL hot, clear
• PKA: pKa 8.1 (Uncertain)
• Water Solubility: soluble
• BRN: 2827
• CAS DataBase Reference: 5,5-Dimethylhydantoin(CAS DataBase Reference)
• NIST Chemistry Reference: 5,5-Dimethylhydantoin(77-71-4)
• EPA Substance Registry System: 5,5-Dimethylhydantoin(77-71-4)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 22-24/25-36/37-26
• WGK Germany: 2
• RTECS: MU0977000
• TSCA: Yes
• Hazardous Substances Data: 77-71-4(Hazardous Substances Data)

Usage

Chemical Properties

white to off-white crystals or crystalline powder

Uses

5,5-Dimethylhydantoin is part of a group of hydantoin compounds that are being evaluated for their anticonvulsant and central nervous system antitumour properties.

Purification Methods

Crystallise the hydantoin from EtOH and sublime it in vacuo. [Beilstein 24 III/IV 1097.]

InChI:InChI=1/C5H8N2O2/c1-5(2)3(8)6-4(9)7-5/h1-2H3,(H2,6,7,8,9)

Synthetic route

potassium cyanate (590-28-3) + methyl 2-aminoisobutyrate hydrochloride (15028-41-8) → 5,5-dimethyl-imidazolidine-2,4-dione (77-71-4)

Conditions	Yield
Stage #1: potassium cyanate; methyl 2-aminoisobutyrate hydrochloride In water Milling; Green chemistry; Stage #2: With potassium carbonate In water Green chemistry;	92%

potassium cyanide + ammonium carbonate (506-87-6) + acetone (67-64-1) → 5,5-dimethyl-imidazolidine-2,4-dione (77-71-4)

Conditions	Yield
In water at 120℃; under 15001.5 Torr; for 0.533333h; Bucherer-Bergs Reaction; Flow reactor;	82%
Stage #1: potassium cyanide; ammonium carbonate; acetone In ethanol; water at 55 - 60℃; Bucherer-Bergs Reaction; Stage #2: With hydrogenchloride In ethanol; water	65%
Stage #1: acetone With sodium metabisulfite Stage #2: potassium cyanide Bucherer-Bergs reaction; Stage #3: ammonium carbonate Bucherer-Bergs reaction;
In ethanol; water at 50 - 80℃; Reflux;

2,3:4,5-bis-O-(isopropylidene)-D-fructopyranose aldehyde (32786-02-0) + ammonium carbonate → 5,5-dimethyl-imidazolidine-2,4-dione (77-71-4) + 3,4:5,6-di-O-isopropylidene-β-D-arabino-DL-glycero-3-heptulopyranosonitrile (116730-70-2, 116730-73-5) + 3,4:5,6-di-O-isopropylidene-β-D-arabino-DL-glycero-3-heptulopyranosoamide (116730-72-4, 116730-76-8)

Conditions	Yield
With potassium cyanide In ethanol; water at 50℃; for 72h;	A 77.8% B 2% C 7.3%

5-[(R)-2-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-2-hydroxy-eth-(Z)-ylidene]-imidazolidine-2,4-dione (116730-53-1) → 5,5-dimethyl-imidazolidine-2,4-dione (77-71-4) + 5-(D-threo-2,3,4-trihydroxybutylidene)imidazol-2,4-dione (116730-55-3)

Conditions	Yield
hydrolysis; Yield given;	A 62.5% B n/a

2,3:4,5-di-O-isopropylidene-D-xylose (3673-15-2, 13039-93-5, 13039-94-6, 23568-31-2, 50866-82-5, 81801-10-7, 120522-08-9, 120522-09-0, 120522-10-3) + ammonium carbonate → 5,5-dimethyl-imidazolidine-2,4-dione (77-71-4) + 5-(D-threo-2,3,4-trihydroxybutylidene)imidazol-2,4-dione (116730-55-3)

Conditions	Yield
With potassium cyanide In ethanol; water at 50℃; for 24h;	A 62.5% B 15%

2,3:4,5-di-O-isopropylidene-D-xylose (3673-15-2, 13039-93-5, 13039-94-6, 23568-31-2, 50866-82-5, 81801-10-7, 120522-08-9, 120522-09-0, 120522-10-3) + ammonium carbonate → 5,5-dimethyl-imidazolidine-2,4-dione (77-71-4) + 5-[(R)-2-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-2-hydroxy-eth-(Z)-ylidene]-imidazolidine-2,4-dione (116730-53-1)

Conditions	Yield
With potassium cyanide In ethanol; water at 50℃; for 24h;	A 62.5% B n/a

carbonic-acid (463-79-6) + 2-amino-2-cyanopropane (19355-69-2) → 5,5-dimethyl-imidazolidine-2,4-dione (77-71-4)

Conditions	Yield
at 25℃; for 24h;	50%

(3aR,5S,5aR,8aS,8bR)-2,2,7,7-Tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-carbaldehyde (4933-77-1) + ammonium carbonate → 5,5-dimethyl-imidazolidine-2,4-dione (77-71-4) + 5-(4,5-isopropylidene-L-gluconor-L-mannono-nitrile-6-yl)hydantoin (116730-74-6, 116837-98-0) + 5-<1,2:3,4-di-O-isopropylidene-α-D-galacto-pentopyranose-5(R)-yl>hydantoin (116730-68-8) + 6-deoxy-1,2:3,4-di-O-isopropylidene-6-ureido-DL-glycero-α-D-galacto-heptopyranuronamide (116730-54-2, 116730-69-9)

Conditions	Yield
With potassium cyanide In ethanol; water at 50℃; for 24h;	A 45% B 2% C 15.7% D 23%

1H-imidazole (288-32-4) + 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione (77-48-5) → 4-bromo-1 H-imidazole (2302-25-2) + 5,5-dimethyl-imidazolidine-2,4-dione (77-71-4)

Conditions	Yield
With sulfuric acid In water at 0℃; for 0.0833333h;	A 21% B 33%

3,4-dihydro-4,4,6-trimethylpyrimidine-2(1H)-thione (5392-23-4) → 5,5-dimethyl-imidazolidine-2,4-dione (77-71-4)

Conditions	Yield
With potassium permanganate; water

2-amino-2-methylpropanamide (16252-90-7) → 5,5-dimethyl-imidazolidine-2,4-dione (77-71-4)

Conditions	Yield
With ethanol; carbon dioxide

2-cyano-2-methylpropanamide (7505-93-3) → 5,5-dimethyl-imidazolidine-2,4-dione (77-71-4)

Conditions	Yield
With potassium hypobromite

(1-Cyan-1-methylethyl)harnstoff (79662-84-3) → 5,5-dimethyl-imidazolidine-2,4-dione (77-71-4)

Conditions	Yield
With hydrogenchloride

N-carbamoyl-α-aminoisobutyric acid (38605-63-9) → 5,5-dimethyl-imidazolidine-2,4-dione (77-71-4)

Conditions	Yield
at 130 - 140℃;
With hydrogenchloride
With hydrogenchloride at 50℃; Rate constant;

ethyl 2-isocyanato-2-methylpropionate (128326-91-0) → 5,5-dimethyl-imidazolidine-2,4-dione (77-71-4)

Conditions	Yield
With ammonium hydroxide anschliessende Cyclisierung mit wss.HCl;

dimethyl-malonic acid bis-bromoamide (861329-91-1) + sodium methylate (124-41-4) → 5,5-dimethyl-imidazolidine-2,4-dione (77-71-4)

Conditions	Yield
erst in der Kaelte, dann in der Hitze;

dimethyl-malonic acid bis-bromoamide (861329-91-1) → 5,5-dimethyl-imidazolidine-2,4-dione (77-71-4)

Conditions	Yield
With sodium methylate

2-Aminoisobutyric acid (62-57-7) + urea (57-13-6) → 5,5-dimethyl-imidazolidine-2,4-dione (77-71-4)

Conditions	Yield
at 160 - 170℃;

ammonium carbamate (1111-78-0) + 2-hydroxy-2-methylpropanenitrile (75-86-5) → 5,5-dimethyl-imidazolidine-2,4-dione (77-71-4)

Conditions	Yield
at 50 - 65℃;

sodium cyanide (143-33-9) + acetone (67-64-1) → 5,5-dimethyl-imidazolidine-2,4-dione (77-71-4)

Conditions	Yield
With ethanol; carbon dioxide; ammonia
With water; ammonium carbonate
With carbon dioxide; water; ammonium carbonate

potassium cyanide (151-50-8) + acetone (67-64-1) → 5,5-dimethyl-imidazolidine-2,4-dione (77-71-4)

Conditions	Yield
With hydrogenchloride; potassium cyanate
With water; ammonium carbonate
With hydrogenchloride; potassium cyanate
With carbon dioxide; water; ammonium carbonate

2-amino-2-cyanopropane (19355-69-2) → 5,5-dimethyl-imidazolidine-2,4-dione (77-71-4)

Conditions	Yield
With carbon dioxide; water

1,3-dibromo-5,5-dimethyl-hydantoin (7072-23-3) → 5,5-dimethyl-imidazolidine-2,4-dione (77-71-4)

Conditions	Yield
With hydrogenchloride; ascorbic acid In water at 30℃;

(1-Carbamoyl-1-methyl-ethyl)-carbamic acid ethyl ester (81587-19-1) → 5,5-dimethyl-imidazolidine-2,4-dione (77-71-4)

Conditions	Yield
With sodium hydroxide In methanol for 1.5h; Ambient temperature;

tert-butyl (1-amino-2-methyl-1-oxopropan-2-yl)carbamate (73470-46-9) → 5,5-dimethyl-imidazolidine-2,4-dione (77-71-4)

Conditions	Yield
With sodium hydroxide In methanol for 1.5h; Ambient temperature;

benzyl N-(2-amino-1,1-dimethyl-2-oxo-ethyl)carbamate (81587-18-0) → 5,5-dimethyl-imidazolidine-2,4-dione (77-71-4)

Conditions	Yield
With sodium hydroxide In methanol for 1.5h; Ambient temperature;

1,3-di(chlorothio)-5,5-dimethylhydantoin (104867-38-1) → 5,5-dimethyl-imidazolidine-2,4-dione (77-71-4)

Conditions	Yield
With water

chlorohydantoin → 5,5-dimethyl-imidazolidine-2,4-dione (77-71-4)

Conditions	Yield
With arsenic(III); potassium iodide In water other reductants;

N-bromo-N'-chloro-5,5-dimethylhydantoin (16079-88-2) → 5,5-dimethyl-imidazolidine-2,4-dione (77-71-4)

Conditions	Yield
With hydrogenchloride; potassium bromide; hydrazine In acetic acid at 32℃; Product distribution; other reductants;

morpholine (110-91-8) + formaldehyd (50-00-0) + 5,5-dimethyl-imidazolidine-2,4-dione (77-71-4) → 5,5-Dimethyl-3-<(morpholin-4-yl)methyl>imidazolidin-2,4-dion (951-13-3)

Conditions	Yield
With 4 A molecular sieve In N,N-dimethyl-formamide for 15h; Ambient temperature;	100%
In methanol for 2h; Condensation;	98%
In ethanol	71%

5,5-dimethyl-imidazolidine-2,4-dione (77-71-4) → 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione (77-48-5)

Conditions	Yield
With bromine	99%
With bromine	99%
With bromine	99%

5,5-dimethyl-imidazolidine-2,4-dione (77-71-4) → 1,3-dichloro-5,5-dimethylhydantoin (118-52-5)

Conditions	Yield
Stage #1: 5,5-dimethyl-imidazolidine-2,4-dione With sodium carbonate at 20℃; for 6h; Stage #2: With chlorine In tetrahydrofuran; ethyl acetate at 100℃; for 7h; Concentration; Microwave irradiation;	98.72%
With trichloroisocyanuric acid In acetonitrile at 20℃; for 0.5h;	87%
With water; chlorine at 8 - 10℃;

Di-tert-butyl acetylenedicarboxylate (66086-33-7) + 5,5-dimethyl-imidazolidine-2,4-dione (77-71-4) + triphenylphosphine (603-35-0) → di-tert-butyl 2-(4,4-dimethyl-2,5-dioxo-imidazolidin-1-yl)-3-(triphenylphosphanylidene)-succinate

Conditions	Yield
In ethyl acetate at 20℃; for 8h;	98%

5,5-dimethyl-imidazolidine-2,4-dione (77-71-4) + 4-cyanobenzyl bromide (17201-43-3) → 4-((4,4-dimethyl-2,5-dioxoimidazolidin-1-yl)methyl)benzonitrile (164648-32-2)

Conditions	Yield
potassium tert-butylate	98%
With potassium carbonate In N,N-dimethyl-formamide at 0 - 20℃; for 12h;	53.5%

4-iodo-2-(trifluoromethyl)benzonitrile (101066-87-9) + 5,5-dimethyl-imidazolidine-2,4-dione (77-71-4) → 4-(4,4-dimethyl-2,5-dioxoimidazolidin-1-yl)-2-(trifluoromethyl)benzonitrile (143782-20-1)

Conditions	Yield
With copper(I) oxide In N,N-dimethyl-formamide at 150℃; for 12h;	98%
With copper(I) oxide In N,N-dimethyl-formamide at 150℃; for 12h;	98%
With copper(I) oxide In N,N-dimethyl-formamide at 150℃; for 14h; Inert atmosphere; regioselective reaction;	82%

5,5-dimethyl-imidazolidine-2,4-dione (77-71-4) + benzyl alcohol (100-51-6) → 3-benzoyl-5,5-dimethylimidazolidine-2,4-dione (1886-18-6)

Conditions	Yield
With iron(III) chloride; calcium hypochlorite; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; sodium hydrogencarbonate In water; acetonitrile at 35℃; for 1.5h; Sealed tube; Inert atmosphere;	98%

5,5-dimethyl-imidazolidine-2,4-dione (77-71-4) + silver nitrate → Ag(1+)*C5H7N2O2(1-)=AgC5H7N2O2

Conditions	Yield
In not given	97%

5,5-dimethyl-imidazolidine-2,4-dione (77-71-4) + cyclohexane-1,2-epoxide (286-20-4) → 3-(2-hydroxy-cyclohexyl)-5,5-dimethyl-imidazolidine-2,4-dione (40388-38-3)

Conditions	Yield
With lithium chloride In N-methyl-acetamide	96.4%

5,5-dimethyl-imidazolidine-2,4-dione (77-71-4) → N-bromo-N'-chloro-5,5-dimethylhydantoin (16079-88-2)

Conditions	Yield
Stage #1: 5,5-dimethyl-imidazolidine-2,4-dione With bromine; sodium hydroxide In water at 5 - 10℃; for 0.25h; Large scale; Stage #2: With chlorine In water for 0.5h; Temperature; Reagent/catalyst; Large scale;	96.3%
With sodium hydroxide; bromine; chlorine In dichloromethane; water
With sodium hydroxide; bromine; chlorine In dichloromethane

5,5-dimethyl-imidazolidine-2,4-dione (77-71-4) + 1,1,1,3,3,3-hexamethyl-disilazane (999-97-3) → 5,5-dimethyl-1,3-bis(TMS)hydantoin (66448-28-0)

Conditions	Yield
In 1,2-dichloro-ethane for 15h; Heating;	96%

N-(oxiran-2-ylmethyl)-N-ethylaniline (19614-67-6) + 5,5-dimethyl-imidazolidine-2,4-dione (77-71-4) → 3-(5,5-dimethylhydantoin-3-yl)-1-(N-ethylanilino)propan-2-ol (1258220-60-8)

Conditions	Yield
In ethanol at 20 - 150℃; for 19h;	96%

5,5-dimethyl-imidazolidine-2,4-dione (77-71-4) + hex-1-yne (693-02-7) → 3-[(Z)-hex-1-en-1-yl]-1,5,5-trimethylimidazolidine-2,4-dione

Conditions	Yield
With [bis(2-methylallyl)cycloocta-1,5-diene]ruthenium(II); 1,4-bis(dicyclohexylphosphino)butane; ytterbium(III) triflate In N,N-dimethyl-formamide at 60℃; for 16h; Inert atmosphere; optical yield given as %de;	96%

5,5-dimethyl-imidazolidine-2,4-dione (77-71-4) + dimethyl acetylenedicarboxylate (762-42-5) + triphenylphosphine (603-35-0) → dimethyl 2-(4,4-dimethyl-2,5-dioxo-imidazolidin-1-yl)-3-(triphenylphosphanylidene)-succinate

Conditions	Yield
In ethyl acetate at 20℃; for 8h;	95%

5,5-dimethyl-imidazolidine-2,4-dione (77-71-4) + benzyl chloride (100-44-7) → 3-benzyl-5,5-dimethyl-2,4-imidazolidinedione (34657-68-6)

Conditions	Yield
With potassium carbonate In DMF (N,N-dimethyl-formamide) at 20℃;	94%
With potassium carbonate In DMF (N,N-dimethyl-formamide) at 20℃;	94%
With sodium hydride In N,N-dimethyl-formamide for 15h; Ambient temperature;	53%

methanol (67-56-1) + 5,5-dimethyl-imidazolidine-2,4-dione (77-71-4) → methyl N-isopropylallophanate (84039-99-6)

Conditions	Yield
for 30h; Irradiation;	93%

5,5-dimethyl-imidazolidine-2,4-dione (77-71-4) + p-methoxybenzyl chloride (824-94-2) → 3-(4-methoxybenzyl)-5,5-dimethylimidazolidine-2,4-dione (220615-80-5)

Conditions	Yield
With potassium carbonate In acetonitrile at 20℃; for 8h; Inert atmosphere;	93%
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 16h;	88.5%
Stage #1: 5,5-dimethyl-imidazolidine-2,4-dione With potassium hydroxide In ethanol at 25 - 90℃; Stage #2: p-methoxybenzyl chloride In methanol; ethanol at 25 - 60℃;	14%

1,8-dibromooctane (4549-32-0) + 5,5-dimethyl-imidazolidine-2,4-dione (77-71-4) → C13H23BrN2O2

Conditions	Yield
Stage #1: 5,5-dimethyl-imidazolidine-2,4-dione With potassium carbonate In acetone at 20℃; for 0.5h; Stage #2: 1,8-dibromooctane In acetone at 20℃; for 3h;	92.4%
Stage #1: 5,5-dimethyl-imidazolidine-2,4-dione With potassium carbonate In acetone for 0.5h; Reflux; Stage #2: 1,8-dibromooctane In acetone Reflux;	92.4%

5,5-dimethyl-imidazolidine-2,4-dione (77-71-4) + allyl bromide (106-95-6) → 1-(Prop-2-enyl)-4,4-dimethyl-2,5-dioxoimidazolidine (3366-92-5)

Conditions	Yield
With potassium hydroxide In methanol; water at 60℃; for 2h;	92%
Stage #1: 5,5-dimethyl-imidazolidine-2,4-dione With sodium hydroxide In water Stage #2: allyl bromide In methanol; water at 60℃; for 1h;	90%
With triethylamine In tetrahydrofuran for 5h; Addition; Heating;

5,5-dimethyl-imidazolidine-2,4-dione (77-71-4) + 1-Bromo-2-chloroethane (107-04-0) → 3-(2'-chloroethyl)-5, 5-dimethylhydantoin (53066-53-8)

Conditions	Yield
With potassium hydroxide In ethanol at 80℃; for 8h;	92%
With potassium hydroxide In ethanol at 80℃; for 8h;	92%
Stage #1: 5,5-dimethyl-imidazolidine-2,4-dione With sodium hydroxide In ethanol at 90℃; for 0.166667h; Stage #2: 1-Bromo-2-chloroethane In ethanol at 80℃; for 8h;	87.6%

5,5-dimethyl-imidazolidine-2,4-dione (77-71-4) + Ethyl 2-bromopropionate (535-11-5, 41978-69-2) → 2-(4,4-dimethyl-2,5-dioxoimidazolidin-1-yl)propionic acid ethyl ester (127834-98-4)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 85℃; for 90h; Inert atmosphere; regioselective reaction;	92%

5,5-dimethyl-imidazolidine-2,4-dione (77-71-4) + benzyl bromide (100-39-0) → 3-benzyl-5,5-dimethyl-2,4-imidazolidinedione (34657-68-6)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 85℃; for 6h; Inert atmosphere; regioselective reaction;	92%
Stage #1: 5,5-dimethyl-imidazolidine-2,4-dione With potassium carbonate In acetone for 0.5h; Reflux; Stage #2: benzyl bromide In acetone at 20℃; for 21h; Reflux;	73%

5,5-dimethyl-imidazolidine-2,4-dione (77-71-4) + bis(4-methylphenyl)iodonium trifluoromethanesulfonate (123726-16-9) → 5,5-dimethyl-3-(p-tolyl)imidazolidine-2,4-dione (92668-56-9)

Conditions	Yield
With potassium phosphate; copper(l) iodide In 1,2-dichloro-ethane at 20℃; for 7h; Inert atmosphere; Schlenk technique; Sealed tube;	92%

5,5-dimethyl-imidazolidine-2,4-dione (77-71-4) + benzyl bromide (100-39-0) → 3-benzyl-1-(3-iodo-2-propynyl-5,5-dimethylhydantoin + 3-benzyl-5,5-dimethyl-2,4-imidazolidinedione (34657-68-6)

Conditions	Yield
With potassium carbonate In acetone	A 91.3% B n/a

2-bromonaphthalene (580-13-2) + 5,5-dimethyl-imidazolidine-2,4-dione (77-71-4) → 5,5-dimethyl-3-(naphthalen-2-yl)hydantoin

Conditions	Yield
With copper(I) oxide In N,N-dimethyl-formamide at 150℃; for 14h; Inert atmosphere; regioselective reaction;	91%

(3-chloropropyl)triethoxysilane (5089-70-3) + 5,5-dimethyl-imidazolidine-2,4-dione (77-71-4) → 5,5-dimethyl-3-(3'-triethoxysilylpropyl)hydantoin (473780-80-2)

Conditions	Yield
Stage #1: 5,5-dimethyl-imidazolidine-2,4-dione With potassium hydroxide In ethanol Heating / reflux; Stage #2: (3-chloropropyl)triethoxysilane In DMF (N,N-dimethyl-formamide) at 60 - 95℃; for 5h;	90.3%
Stage #1: 5,5-dimethyl-imidazolidine-2,4-dione With sodium hydroxide In ethanol at 90℃; for 0.166667h; Stage #2: (3-chloropropyl)triethoxysilane In N,N-dimethyl-formamide at 95℃; for 10h;

5,5-dimethyl-imidazolidine-2,4-dione (77-71-4) → 1,3-Diiodo-5,5-dimethyl-2,4-imidazolidinedione (2232-12-4)

Conditions	Yield
With sodium hypochlorite; iodine In acetic acid butyl ester; water at 10℃; for 2h; Solvent; Reagent/catalyst;	90%
With Iodine monochloride; sodium hydroxide In chloroform; water at -5 - 5℃; for 2h;	63.3%
With sodium hydroxide; Iodine monochloride In chloroform at 0℃; for 0.25h;	48%

5,5-dimethyl-imidazolidine-2,4-dione (77-71-4) → 3-amino-5,5'-dimethylimidazolidine-2,4-dione (1123-44-0)

Conditions	Yield
With hydrazine hydrate	90%
With hydrazine hydrate
With hydrazine hydrate Heating;
With hydrazine hydrate

Upstream product

• 5392-23-4 3,4-dihydro-4,4,6-trimethylpyrimidine-2(1H)-thione 
• 7505-93-3 2-cyano-2-methylpropanamide 
• 38605-63-9 N-carbamoyl-α-aminoisobutyric acid 
• 128326-91-0 ethyl 2-isocyanato-2-methylpropionate 
• 861329-91-1 dimethyl-malonic acid bis-bromoamide 
• 124-41-4 sodium methylate 
• 1111-78-0 ammonium carbamate 
• 75-86-5 2-hydroxy-2-methylpropanenitrile 
• 19355-69-2 2-amino-2-cyanopropane 
• 81587-18-0 benzyl N-(2-amino-1,1-dimethyl-2-oxo-ethyl)carbamate 
• 590-28-3 potassium cyanate 
• 123-42-2 4-Hydroxy-4-methyl-2-pentanone 
• 151-50-8 potassium cyanide 
• 67-64-1 acetone 

Downstream Products

• 116-25-6 1-(hydroxymethyl)-5,5-dimethyl hydantoin 
• 6921-17-1 1-chloro-5,5-dimethylhydantoin 
• 77-48-5 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione 
• 6341-67-9 1-acetyl-5,5-dimethylhydantoin 
• 34657-68-6 3-benzyl-5,5-dimethylimidazolidine-2,4-dione 
• 20513-25-1 5,5-dimethylimidazolidine-2,4-dithione 
• 7072-23-3 1,3-dibromo-5,5-dimethyl-hydantoin 
• 118-52-5 1,3-dichloro-5,5-dimethylhydantoin 
• 2232-12-4 1,3-Diiodo-5,5-dimethyl-2,4-imidazolidinedione 
• 62-57-7 2-Aminoisobutyric acid 
• 190579-87-4 3-isopropyl-5,5-dimethylhydantoin 
• 7664-41-7 ammonia 
• 15719-64-9 methylammonium carbonate 
• 143782-20-1 4-(4,4-dimethyl-2,5-dioxoimidazolidin-1-yl)-2-(trifluoromethyl)benzonitrile 

Relevant articles and documents

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Synthesis and in vivo hypoglycemic activity of new imidazolidine-2,4-dione derivatives

A series of new 3-arylsulfonylimidazolidine-2,4-diones (2a-2p) were synthesized by reacting imidazolidine-2,4-diones (1a-1e) with arylsulfonyl chlorides in the presence of triethyl amine. The imidazolidine-2,4-diones (1a-1e) were in turn synthesized from the corresponding ketones through Bucherer-Bergs reaction. All the synthesized compounds were characterized on the basis of their spectral (IR, 1H and 13C NMR and MS) and microanalytical data. The hypoglycemic activity of the compounds (2a-2p) was evaluated using alloxanized diabetic rat model. Compound 2a showed an excellent activity with a reduction in the blood glucose level of -286 ± 7 mg/dL after 5 h of drug administration as compared to -270 ± 8 mg/dL for glipizide. The hypoglycemic activity of compound 2b (-268 ± 9 mg/dL) was also comparable to the standard drug. However, only moderate activity was observed for compound 2e.

Fast halogenation of some N-heterocycles by means of N,N'-dihalo-5,5- dimethylhydantoin

An instantaneous, selective and high-yielding halogenation process is reported. The method operates with imidazoles, pyrazoles, and indoles under benign reaction conditions. The developed process involves the use of N,N'-dihalo-5,5-dimethylhydantoins (halo=chlorine, bromine, iodine) as halogenation reagents that are activated by catalytic quantities of a strong Bronsted acid. Moreover, the halogenation process is switchable to produce either the mono- or di-halogenated products. Issues related to the reaction mechanism are investigated and a proposal for a reaction mechanism is disclosed.