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77-71-4

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77-71-4 Usage

Description

5,5-Dimethylhydantoin is a hydantoin compound that is being evaluated for its potential anticonvulsant and central nervous system antitumor properties.

Uses

Used in Pharmaceutical Industry:
5,5-Dimethylhydantoin is used as a pharmaceutical compound for its potential anticonvulsant properties, which can help in the treatment of seizures and epilepsy.
Used in Oncology Research:
5,5-Dimethylhydantoin is used as a research compound for its potential central nervous system antitumor properties, which can aid in the development of new treatments for brain tumors and other related cancers.

Purification Methods

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

Check Digit Verification of cas no

The CAS Registry Mumber 77-71-4 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 7 and 7 respectively; the second part has 2 digits, 7 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 77-71:
(4*7)+(3*7)+(2*7)+(1*1)=64
64 % 10 = 4
So 77-71-4 is a valid CAS Registry Number.
InChI:InChI=1/C5H8N2O2/c1-5(2)3(8)6-4(9)7-5/h1-2H3,(H2,6,7,8,9)

77-71-4 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
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  • Detail
  • Alfa Aesar

  • (L03388)  5,5-Dimethylhydantoin, 97%   

  • 77-71-4

  • 100g

  • 230.0CNY

  • Detail
  • Alfa Aesar

  • (L03388)  5,5-Dimethylhydantoin, 97%   

  • 77-71-4

  • 500g

  • 666.0CNY

  • Detail
  • Aldrich

  • (D161403)  5,5-Dimethylhydantoin  97%

  • 77-71-4

  • D161403-100G

  • 321.75CNY

  • Detail
  • Aldrich

  • (D161403)  5,5-Dimethylhydantoin  97%

  • 77-71-4

  • D161403-1KG

  • 946.53CNY

  • Detail

77-71-4SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name 5,5-Dimethylhydantoin

1.2 Other means of identification

Product number -
Other names 2,4-Imidazolidinedione, 5,5-dimethyl-

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Intermediates,Ion exchange agents
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:77-71-4 SDS

77-71-4Synthetic route

potassium cyanate
590-28-3

potassium cyanate

methyl 2-aminoisobutyrate hydrochloride
15028-41-8

methyl 2-aminoisobutyrate hydrochloride

5,5-dimethyl-imidazolidine-2,4-dione
77-71-4

5,5-dimethyl-imidazolidine-2,4-dione

Conditions
ConditionsYield
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

potassium cyanide

ammonium carbonate
506-87-6

ammonium carbonate

acetone
67-64-1

acetone

5,5-dimethyl-imidazolidine-2,4-dione
77-71-4

5,5-dimethyl-imidazolidine-2,4-dione

Conditions
ConditionsYield
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

2,3:4,5-bis-O-(isopropylidene)-D-fructopyranose aldehyde

ammonium carbonate

ammonium carbonate

A

5,5-dimethyl-imidazolidine-2,4-dione
77-71-4

5,5-dimethyl-imidazolidine-2,4-dione

B

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-heptulopyranosonitrile

C

3,4:5,6-di-O-isopropylidene-β-D-arabino-DL-glycero-3-heptulopyranosoamide
116730-72-4, 116730-76-8

3,4:5,6-di-O-isopropylidene-β-D-arabino-DL-glycero-3-heptulopyranosoamide

Conditions
ConditionsYield
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-[(R)-2-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-2-hydroxy-eth-(Z)-ylidene]-imidazolidine-2,4-dione

A

5,5-dimethyl-imidazolidine-2,4-dione
77-71-4

5,5-dimethyl-imidazolidine-2,4-dione

B

5-(D-threo-2,3,4-trihydroxybutylidene)imidazol-2,4-dione
116730-55-3

5-(D-threo-2,3,4-trihydroxybutylidene)imidazol-2,4-dione

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

ammonium carbonate

A

5,5-dimethyl-imidazolidine-2,4-dione
77-71-4

5,5-dimethyl-imidazolidine-2,4-dione

B

5-(D-threo-2,3,4-trihydroxybutylidene)imidazol-2,4-dione
116730-55-3

5-(D-threo-2,3,4-trihydroxybutylidene)imidazol-2,4-dione

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

ammonium carbonate

A

5,5-dimethyl-imidazolidine-2,4-dione
77-71-4

5,5-dimethyl-imidazolidine-2,4-dione

B

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-[(R)-2-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-2-hydroxy-eth-(Z)-ylidene]-imidazolidine-2,4-dione

Conditions
ConditionsYield
With potassium cyanide In ethanol; water at 50℃; for 24h;A 62.5%
B n/a
carbonic-acid
463-79-6

carbonic-acid

2-amino-2-cyanopropane
19355-69-2

2-amino-2-cyanopropane

5,5-dimethyl-imidazolidine-2,4-dione
77-71-4

5,5-dimethyl-imidazolidine-2,4-dione

Conditions
ConditionsYield
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

(3aR,5S,5aR,8aS,8bR)-2,2,7,7-Tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-carbaldehyde

ammonium carbonate

ammonium carbonate

A

5,5-dimethyl-imidazolidine-2,4-dione
77-71-4

5,5-dimethyl-imidazolidine-2,4-dione

B

5-(4,5-isopropylidene-L-gluconor-L-mannono-nitrile-6-yl)hydantoin
116730-74-6, 116837-98-0

5-(4,5-isopropylidene-L-gluconor-L-mannono-nitrile-6-yl)hydantoin

C

5-<1,2:3,4-di-O-isopropylidene-α-D-galacto-pentopyranose-5(R)-yl>hydantoin
116730-68-8

5-<1,2:3,4-di-O-isopropylidene-α-D-galacto-pentopyranose-5(R)-yl>hydantoin

D

6-deoxy-1,2:3,4-di-O-isopropylidene-6-ureido-DL-glycero-α-D-galacto-heptopyranuronamide
116730-54-2, 116730-69-9

6-deoxy-1,2:3,4-di-O-isopropylidene-6-ureido-DL-glycero-α-D-galacto-heptopyranuronamide

Conditions
ConditionsYield
With potassium cyanide In ethanol; water at 50℃; for 24h;A 45%
B 2%
C 15.7%
D 23%
1H-imidazole
288-32-4

1H-imidazole

1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione
77-48-5

1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione

A

4-bromo-1 H-imidazole
2302-25-2

4-bromo-1 H-imidazole

B

5,5-dimethyl-imidazolidine-2,4-dione
77-71-4

5,5-dimethyl-imidazolidine-2,4-dione

Conditions
ConditionsYield
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

3,4-dihydro-4,4,6-trimethylpyrimidine-2(1H)-thione

5,5-dimethyl-imidazolidine-2,4-dione
77-71-4

5,5-dimethyl-imidazolidine-2,4-dione

Conditions
ConditionsYield
With potassium permanganate; water
2-amino-2-methylpropanamide
16252-90-7

2-amino-2-methylpropanamide

5,5-dimethyl-imidazolidine-2,4-dione
77-71-4

5,5-dimethyl-imidazolidine-2,4-dione

Conditions
ConditionsYield
With ethanol; carbon dioxide
2-cyano-2-methylpropanamide
7505-93-3

2-cyano-2-methylpropanamide

5,5-dimethyl-imidazolidine-2,4-dione
77-71-4

5,5-dimethyl-imidazolidine-2,4-dione

Conditions
ConditionsYield
With potassium hypobromite
(1-Cyan-1-methylethyl)harnstoff
79662-84-3

(1-Cyan-1-methylethyl)harnstoff

5,5-dimethyl-imidazolidine-2,4-dione
77-71-4

5,5-dimethyl-imidazolidine-2,4-dione

Conditions
ConditionsYield
With hydrogenchloride
N-carbamoyl-α-aminoisobutyric acid
38605-63-9

N-carbamoyl-α-aminoisobutyric acid

5,5-dimethyl-imidazolidine-2,4-dione
77-71-4

5,5-dimethyl-imidazolidine-2,4-dione

Conditions
ConditionsYield
at 130 - 140℃;
With hydrogenchloride
With hydrogenchloride at 50℃; Rate constant;
ethyl 2-isocyanato-2-methylpropionate
128326-91-0

ethyl 2-isocyanato-2-methylpropionate

5,5-dimethyl-imidazolidine-2,4-dione
77-71-4

5,5-dimethyl-imidazolidine-2,4-dione

Conditions
ConditionsYield
With ammonium hydroxide anschliessende Cyclisierung mit wss.HCl;
dimethyl-malonic acid bis-bromoamide
861329-91-1

dimethyl-malonic acid bis-bromoamide

sodium methylate
124-41-4

sodium methylate

5,5-dimethyl-imidazolidine-2,4-dione
77-71-4

5,5-dimethyl-imidazolidine-2,4-dione

Conditions
ConditionsYield
erst in der Kaelte, dann in der Hitze;
dimethyl-malonic acid bis-bromoamide
861329-91-1

dimethyl-malonic acid bis-bromoamide

5,5-dimethyl-imidazolidine-2,4-dione
77-71-4

5,5-dimethyl-imidazolidine-2,4-dione

Conditions
ConditionsYield
With sodium methylate
2-Aminoisobutyric acid
62-57-7

2-Aminoisobutyric acid

urea
57-13-6

urea

5,5-dimethyl-imidazolidine-2,4-dione
77-71-4

5,5-dimethyl-imidazolidine-2,4-dione

Conditions
ConditionsYield
at 160 - 170℃;
ammonium carbamate
1111-78-0

ammonium carbamate

2-hydroxy-2-methylpropanenitrile
75-86-5

2-hydroxy-2-methylpropanenitrile

5,5-dimethyl-imidazolidine-2,4-dione
77-71-4

5,5-dimethyl-imidazolidine-2,4-dione

Conditions
ConditionsYield
at 50 - 65℃;
sodium cyanide
143-33-9

sodium cyanide

acetone
67-64-1

acetone

5,5-dimethyl-imidazolidine-2,4-dione
77-71-4

5,5-dimethyl-imidazolidine-2,4-dione

Conditions
ConditionsYield
With ethanol; carbon dioxide; ammonia
With water; ammonium carbonate
With carbon dioxide; water; ammonium carbonate
potassium cyanide
151-50-8

potassium cyanide

acetone
67-64-1

acetone

5,5-dimethyl-imidazolidine-2,4-dione
77-71-4

5,5-dimethyl-imidazolidine-2,4-dione

Conditions
ConditionsYield
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

2-amino-2-cyanopropane

5,5-dimethyl-imidazolidine-2,4-dione
77-71-4

5,5-dimethyl-imidazolidine-2,4-dione

Conditions
ConditionsYield
With carbon dioxide; water
1,3-dibromo-5,5-dimethyl-hydantoin
7072-23-3

1,3-dibromo-5,5-dimethyl-hydantoin

5,5-dimethyl-imidazolidine-2,4-dione
77-71-4

5,5-dimethyl-imidazolidine-2,4-dione

Conditions
ConditionsYield
With hydrogenchloride; ascorbic acid In water at 30℃;
(1-Carbamoyl-1-methyl-ethyl)-carbamic acid ethyl ester
81587-19-1

(1-Carbamoyl-1-methyl-ethyl)-carbamic acid ethyl ester

5,5-dimethyl-imidazolidine-2,4-dione
77-71-4

5,5-dimethyl-imidazolidine-2,4-dione

Conditions
ConditionsYield
With sodium hydroxide In methanol for 1.5h; Ambient temperature;
tert-butyl (1-amino-2-methyl-1-oxopropan-2-yl)carbamate
73470-46-9

tert-butyl (1-amino-2-methyl-1-oxopropan-2-yl)carbamate

5,5-dimethyl-imidazolidine-2,4-dione
77-71-4

5,5-dimethyl-imidazolidine-2,4-dione

Conditions
ConditionsYield
With sodium hydroxide In methanol for 1.5h; Ambient temperature;
benzyl N-(2-amino-1,1-dimethyl-2-oxo-ethyl)carbamate
81587-18-0

benzyl N-(2-amino-1,1-dimethyl-2-oxo-ethyl)carbamate

5,5-dimethyl-imidazolidine-2,4-dione
77-71-4

5,5-dimethyl-imidazolidine-2,4-dione

Conditions
ConditionsYield
With sodium hydroxide In methanol for 1.5h; Ambient temperature;
1,3-di(chlorothio)-5,5-dimethylhydantoin
104867-38-1

1,3-di(chlorothio)-5,5-dimethylhydantoin

5,5-dimethyl-imidazolidine-2,4-dione
77-71-4

5,5-dimethyl-imidazolidine-2,4-dione

Conditions
ConditionsYield
With water
chlorohydantoin

chlorohydantoin

5,5-dimethyl-imidazolidine-2,4-dione
77-71-4

5,5-dimethyl-imidazolidine-2,4-dione

Conditions
ConditionsYield
With arsenic(III); potassium iodide In water other reductants;
N-bromo-N'-chloro-5,5-dimethylhydantoin
16079-88-2

N-bromo-N'-chloro-5,5-dimethylhydantoin

5,5-dimethyl-imidazolidine-2,4-dione
77-71-4

5,5-dimethyl-imidazolidine-2,4-dione

Conditions
ConditionsYield
With hydrogenchloride; potassium bromide; hydrazine In acetic acid at 32℃; Product distribution; other reductants;
morpholine
110-91-8

morpholine

formaldehyd
50-00-0

formaldehyd

5,5-dimethyl-imidazolidine-2,4-dione
77-71-4

5,5-dimethyl-imidazolidine-2,4-dione

5,5-Dimethyl-3-<(morpholin-4-yl)methyl>imidazolidin-2,4-dion
951-13-3

5,5-Dimethyl-3-<(morpholin-4-yl)methyl>imidazolidin-2,4-dion

Conditions
ConditionsYield
With 4 A molecular sieve In N,N-dimethyl-formamide for 15h; Ambient temperature;100%
In methanol for 2h; Condensation;98%
In ethanol71%
5,5-dimethyl-imidazolidine-2,4-dione
77-71-4

5,5-dimethyl-imidazolidine-2,4-dione

1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione
77-48-5

1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione

Conditions
ConditionsYield
With bromine99%
With bromine99%
With bromine99%
5,5-dimethyl-imidazolidine-2,4-dione
77-71-4

5,5-dimethyl-imidazolidine-2,4-dione

1,3-dichloro-5,5-dimethylhydantoin
118-52-5

1,3-dichloro-5,5-dimethylhydantoin

Conditions
ConditionsYield
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

Di-tert-butyl acetylenedicarboxylate

5,5-dimethyl-imidazolidine-2,4-dione
77-71-4

5,5-dimethyl-imidazolidine-2,4-dione

triphenylphosphine
603-35-0

triphenylphosphine

di-tert-butyl 2-(4,4-dimethyl-2,5-dioxo-imidazolidin-1-yl)-3-(triphenylphosphanylidene)-succinate

di-tert-butyl 2-(4,4-dimethyl-2,5-dioxo-imidazolidin-1-yl)-3-(triphenylphosphanylidene)-succinate

Conditions
ConditionsYield
In ethyl acetate at 20℃; for 8h;98%
5,5-dimethyl-imidazolidine-2,4-dione
77-71-4

5,5-dimethyl-imidazolidine-2,4-dione

4-cyanobenzyl bromide
17201-43-3

4-cyanobenzyl bromide

4-((4,4-dimethyl-2,5-dioxoimidazolidin-1-yl)methyl)benzonitrile
164648-32-2

4-((4,4-dimethyl-2,5-dioxoimidazolidin-1-yl)methyl)benzonitrile

Conditions
ConditionsYield
potassium tert-butylate98%
With potassium carbonate In N,N-dimethyl-formamide at 0 - 20℃; for 12h;53.5%
4-iodo-2-(trifluoromethyl)benzonitrile
101066-87-9

4-iodo-2-(trifluoromethyl)benzonitrile

5,5-dimethyl-imidazolidine-2,4-dione
77-71-4

5,5-dimethyl-imidazolidine-2,4-dione

4-(4,4-dimethyl-2,5-dioxoimidazolidin-1-yl)-2-(trifluoromethyl)benzonitrile
143782-20-1

4-(4,4-dimethyl-2,5-dioxoimidazolidin-1-yl)-2-(trifluoromethyl)benzonitrile

Conditions
ConditionsYield
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

5,5-dimethyl-imidazolidine-2,4-dione

benzyl alcohol
100-51-6

benzyl alcohol

3-benzoyl-5,5-dimethylimidazolidine-2,4-dione
1886-18-6

3-benzoyl-5,5-dimethylimidazolidine-2,4-dione

Conditions
ConditionsYield
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

5,5-dimethyl-imidazolidine-2,4-dione

silver nitrate

silver nitrate

Ag(1+)*C5H7N2O2(1-)=AgC5H7N2O2

Ag(1+)*C5H7N2O2(1-)=AgC5H7N2O2

Conditions
ConditionsYield
In not given97%
5,5-dimethyl-imidazolidine-2,4-dione
77-71-4

5,5-dimethyl-imidazolidine-2,4-dione

cyclohexane-1,2-epoxide
286-20-4

cyclohexane-1,2-epoxide

3-(2-hydroxy-cyclohexyl)-5,5-dimethyl-imidazolidine-2,4-dione
40388-38-3

3-(2-hydroxy-cyclohexyl)-5,5-dimethyl-imidazolidine-2,4-dione

Conditions
ConditionsYield
With lithium chloride In N-methyl-acetamide96.4%
5,5-dimethyl-imidazolidine-2,4-dione
77-71-4

5,5-dimethyl-imidazolidine-2,4-dione

N-bromo-N'-chloro-5,5-dimethylhydantoin
16079-88-2

N-bromo-N'-chloro-5,5-dimethylhydantoin

Conditions
ConditionsYield
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

5,5-dimethyl-imidazolidine-2,4-dione

1,1,1,3,3,3-hexamethyl-disilazane
999-97-3

1,1,1,3,3,3-hexamethyl-disilazane

5,5-dimethyl-1,3-bis(TMS)hydantoin
66448-28-0

5,5-dimethyl-1,3-bis(TMS)hydantoin

Conditions
ConditionsYield
In 1,2-dichloro-ethane for 15h; Heating;96%
N-(oxiran-2-ylmethyl)-N-ethylaniline
19614-67-6

N-(oxiran-2-ylmethyl)-N-ethylaniline

5,5-dimethyl-imidazolidine-2,4-dione
77-71-4

5,5-dimethyl-imidazolidine-2,4-dione

3-(5,5-dimethylhydantoin-3-yl)-1-(N-ethylanilino)propan-2-ol
1258220-60-8

3-(5,5-dimethylhydantoin-3-yl)-1-(N-ethylanilino)propan-2-ol

Conditions
ConditionsYield
In ethanol at 20 - 150℃; for 19h;96%
5,5-dimethyl-imidazolidine-2,4-dione
77-71-4

5,5-dimethyl-imidazolidine-2,4-dione

hex-1-yne
693-02-7

hex-1-yne

3-[(Z)-hex-1-en-1-yl]-1,5,5-trimethylimidazolidine-2,4-dione

3-[(Z)-hex-1-en-1-yl]-1,5,5-trimethylimidazolidine-2,4-dione

Conditions
ConditionsYield
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

5,5-dimethyl-imidazolidine-2,4-dione

dimethyl acetylenedicarboxylate
762-42-5

dimethyl acetylenedicarboxylate

triphenylphosphine
603-35-0

triphenylphosphine

dimethyl 2-(4,4-dimethyl-2,5-dioxo-imidazolidin-1-yl)-3-(triphenylphosphanylidene)-succinate

dimethyl 2-(4,4-dimethyl-2,5-dioxo-imidazolidin-1-yl)-3-(triphenylphosphanylidene)-succinate

Conditions
ConditionsYield
In ethyl acetate at 20℃; for 8h;95%
5,5-dimethyl-imidazolidine-2,4-dione
77-71-4

5,5-dimethyl-imidazolidine-2,4-dione

benzyl chloride
100-44-7

benzyl chloride

3-benzyl-5,5-dimethyl-2,4-imidazolidinedione
34657-68-6

3-benzyl-5,5-dimethyl-2,4-imidazolidinedione

Conditions
ConditionsYield
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

methanol

5,5-dimethyl-imidazolidine-2,4-dione
77-71-4

5,5-dimethyl-imidazolidine-2,4-dione

methyl N-isopropylallophanate
84039-99-6

methyl N-isopropylallophanate

Conditions
ConditionsYield
for 30h; Irradiation;93%
5,5-dimethyl-imidazolidine-2,4-dione
77-71-4

5,5-dimethyl-imidazolidine-2,4-dione

p-methoxybenzyl chloride
824-94-2

p-methoxybenzyl chloride

3-(4-methoxybenzyl)-5,5-dimethylimidazolidine-2,4-dione
220615-80-5

3-(4-methoxybenzyl)-5,5-dimethylimidazolidine-2,4-dione

Conditions
ConditionsYield
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

1,8-dibromooctane

5,5-dimethyl-imidazolidine-2,4-dione
77-71-4

5,5-dimethyl-imidazolidine-2,4-dione

C13H23BrN2O2

C13H23BrN2O2

Conditions
ConditionsYield
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

5,5-dimethyl-imidazolidine-2,4-dione

allyl bromide
106-95-6

allyl bromide

1-(Prop-2-enyl)-4,4-dimethyl-2,5-dioxoimidazolidine
3366-92-5

1-(Prop-2-enyl)-4,4-dimethyl-2,5-dioxoimidazolidine

Conditions
ConditionsYield
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

5,5-dimethyl-imidazolidine-2,4-dione

1-Bromo-2-chloroethane
107-04-0

1-Bromo-2-chloroethane

3-(2'-chloroethyl)-5, 5-dimethylhydantoin
53066-53-8

3-(2'-chloroethyl)-5, 5-dimethylhydantoin

Conditions
ConditionsYield
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

5,5-dimethyl-imidazolidine-2,4-dione

Ethyl 2-bromopropionate
535-11-5, 41978-69-2

Ethyl 2-bromopropionate

2-(4,4-dimethyl-2,5-dioxoimidazolidin-1-yl)propionic acid ethyl ester
127834-98-4

2-(4,4-dimethyl-2,5-dioxoimidazolidin-1-yl)propionic acid ethyl ester

Conditions
ConditionsYield
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

5,5-dimethyl-imidazolidine-2,4-dione

benzyl bromide
100-39-0

benzyl bromide

3-benzyl-5,5-dimethyl-2,4-imidazolidinedione
34657-68-6

3-benzyl-5,5-dimethyl-2,4-imidazolidinedione

Conditions
ConditionsYield
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

5,5-dimethyl-imidazolidine-2,4-dione

bis(4-methylphenyl)iodonium trifluoromethanesulfonate
123726-16-9

bis(4-methylphenyl)iodonium trifluoromethanesulfonate

5,5-dimethyl-3-(p-tolyl)imidazolidine-2,4-dione
92668-56-9

5,5-dimethyl-3-(p-tolyl)imidazolidine-2,4-dione

Conditions
ConditionsYield
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

5,5-dimethyl-imidazolidine-2,4-dione

benzyl bromide
100-39-0

benzyl bromide

A

3-benzyl-1-(3-iodo-2-propynyl-5,5-dimethylhydantoin

3-benzyl-1-(3-iodo-2-propynyl-5,5-dimethylhydantoin

B

3-benzyl-5,5-dimethyl-2,4-imidazolidinedione
34657-68-6

3-benzyl-5,5-dimethyl-2,4-imidazolidinedione

Conditions
ConditionsYield
With potassium carbonate In acetoneA 91.3%
B n/a
2-bromonaphthalene
580-13-2

2-bromonaphthalene

5,5-dimethyl-imidazolidine-2,4-dione
77-71-4

5,5-dimethyl-imidazolidine-2,4-dione

5,5-dimethyl-3-(naphthalen-2-yl)hydantoin

5,5-dimethyl-3-(naphthalen-2-yl)hydantoin

Conditions
ConditionsYield
With copper(I) oxide In N,N-dimethyl-formamide at 150℃; for 14h; Inert atmosphere; regioselective reaction;91%
(3-chloropropyl)triethoxysilane
5089-70-3

(3-chloropropyl)triethoxysilane

5,5-dimethyl-imidazolidine-2,4-dione
77-71-4

5,5-dimethyl-imidazolidine-2,4-dione

5,5-dimethyl-3-(3'-triethoxysilylpropyl)hydantoin
473780-80-2

5,5-dimethyl-3-(3'-triethoxysilylpropyl)hydantoin

Conditions
ConditionsYield
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

5,5-dimethyl-imidazolidine-2,4-dione

1,3-Diiodo-5,5-dimethyl-2,4-imidazolidinedione
2232-12-4

1,3-Diiodo-5,5-dimethyl-2,4-imidazolidinedione

Conditions
ConditionsYield
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

5,5-dimethyl-imidazolidine-2,4-dione

3-amino-5,5'-dimethylimidazolidine-2,4-dione
1123-44-0

3-amino-5,5'-dimethylimidazolidine-2,4-dione

Conditions
ConditionsYield
With hydrazine hydrate90%
With hydrazine hydrate
With hydrazine hydrate Heating;
With hydrazine hydrate

77-71-4Relevant articles and documents

-

Bucherer,Brandt

, p. 145 ()

-

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

Hussain, Abid,Kashif, Muhammad Kalim,Naseer, Muhammad Moazzam,Rana, Usman A.,Hameed, Shahid

, p. 7313 - 7326 (2015/09/29)

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.

AMIDOALKYLPIPERAZINYL DERIVATIVES FOR THE TREATMENT OF CENTRAL NERVOUS SYSTEM DISEASES

-

Page/Page column 29; 30, (2013/03/26)

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.

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