930-33-6

Usage

Chemical Properties

white solid

Flammability and Explosibility

Notclassified

InChI:InChI=1/C2H3N3O/c6-2-3-1-4-5-2/h1H,(H2,3,4,5,6)

Synthetic route

semicarbazide hydrochloride (563-41-7) → 2,4-dihydro-1,2,4-triazol-3-one (930-33-6)

Conditions	Yield
With trimethyl orthoformate In methanol; toluene	100%

N4-semicarbazide hydrochloride + trimethyl orthoformate (149-73-5) → 2,4-dihydro-1,2,4-triazol-3-one (930-33-6)

Conditions	Yield
In methanol at 20℃; for 2h;	100%

formic acid (64-18-6) + semicarbazide hydrochloride (563-41-7) → 2,4-dihydro-1,2,4-triazol-3-one (930-33-6)

Conditions	Yield
In water at 106℃; for 4h;	95%
for 2h; Heating;	86%
at 90 - 106℃; for 7h;	82%
at 75℃; for 6h;	81%

semicarbazide hydrochloride (563-41-7) + orthoformic acid triethyl ester (122-51-0) → 2,4-dihydro-1,2,4-triazol-3-one (930-33-6)

Conditions	Yield
for 2.5h; Heating;	91%
for 2h; Condensation; Heating;

5-amino-2,4-dihydro-3H-1,2,4-triazol-3-one (1003-35-6) → 2,4-dihydro-1,2,4-triazol-3-one (930-33-6)

Conditions	Yield
With acetic acid; sodium nitrite for 4h; Deamination;	74%

5-oxo-4,5-dihydro-1,2,4-triazole-3-carboxylic acid (4538-16-3) → 2,4-dihydro-1,2,4-triazol-3-one (930-33-6)

Conditions	Yield
Heating;	63%

2-ethyl-2,4-dihydro-[1,2,4]triazole-3-thione (29983-26-4) → 2-ethyl-1,2,4-triazol-3(2H)-one (4114-42-5) + 2,4-dihydro-1,2,4-triazol-3-one (930-33-6)

Conditions	Yield
at 800℃; under 0.01 Torr;	A 60% B 2%

2-β-cyanoethyl-1,2,4-triazol-3(2H)-one (537698-45-6) → acrylonitrile (107-13-1) + 2,4-dihydro-1,2,4-triazol-3-one (930-33-6)

Conditions	Yield
at 800℃; under 0.01 Torr;	A 43% B 4%

4-p-chlorobenzylideneimino-1,2,4-triazol-3(2H)-one → 4-Cyanochlorobenzene (623-03-0) + 2,4-dihydro-1,2,4-triazol-3-one (930-33-6)

Conditions	Yield
at 500℃; under 0.01 Torr;	A n/a B 25%

1,3,5-Triazine (290-87-9) + hydrazine carboxamide (4426-72-6, 51433-48-8) → 2,4-dihydro-1,2,4-triazol-3-one (930-33-6)

hydrazine carboxamide (4426-72-6, 51433-48-8) + orthoformic acid triethyl ester (122-51-0) → 2,4-dihydro-1,2,4-triazol-3-one (930-33-6)

4-chlorobenzylidenimino-2-ethyl-1,2,4-triazol-3(2H)-one → 4-Cyanochlorobenzene (623-03-0) + 2-ethyl-1,2,4-triazol-3(2H)-one (4114-42-5) + 2,4-dihydro-1,2,4-triazol-3-one (930-33-6)

Conditions	Yield
at 226.85℃; under 0.01 Torr; Kinetics; Activation energy; Further Variations:; Temperatures;

4-chlorobenzylidenimino-2-β-cyanoethyl-1,2,4-triazol-3(2H)-one → 4-Cyanochlorobenzene (623-03-0) + acrylonitrile (107-13-1) + 2,4-dihydro-1,2,4-triazol-3-one (930-33-6) + 2-β-cyanoethyl-1,2,4-triazol-3(2H)-one (537698-45-6)

Conditions	Yield
at 226.85℃; under 0.01 Torr; Kinetics; Activation energy; Further Variations:; Temperatures;

3(5)-amino-1,2,4-triazole (61-82-5) → 2,4-dihydro-1,2,4-triazol-3-one (930-33-6)

Conditions	Yield
With sulfuric acid; sodium nitrite at 5 - 100℃; for 10h;
With sulfuric acid; sodium nitrite In water at 5 - 100℃; for 2h;

2,4-dihydro-1,2,4-triazol-3-one (930-33-6) → 3-nitro-1,2,4-triazol-5-one (932-64-9)

Conditions	Yield
With sulfuric acid; nitric acid In water at 65℃; for 2h;	96%
With nitric acid at 50 - 85℃; for 0.5h;	84%
With nitric acid at 54.9 - 59.9℃;
With sulfuric acid; nitric acid
With sulfuric acid; nitric acid In water at 65℃; for 2h;

2-cyano-1-phenylacetylene (935-02-4) + 2,4-dihydro-1,2,4-triazol-3-one (930-33-6) → 2,4-bis(1-phenyl-2-cyanovinylene)-1,2,4-triazol-3-one (83749-87-5)

Conditions	Yield
	88%

1-adamanthanol (768-95-6) + 2,4-dihydro-1,2,4-triazol-3-one (930-33-6) → 1-(1-adamantyl)-1,2,4-triazol-5(1H,4H)-one

Conditions	Yield
With sulfuric acid In water at 20℃; for 1.25h;	84%

formaldehyd (50-00-0) + 2,4-dihydro-1,2,4-triazol-3-one (930-33-6) → 4,4'-Methylenebis-1,2,4-triazole-5,5-dione

Conditions	Yield
With hydrogenchloride; water Alkylation; Heating;	75%

formaldehyd (50-00-0) + 2,4-dihydro-1,2,4-triazol-3-one (930-33-6) → 1,4-dihydroxymethyl-1,2,4-triazol-5-one (78663-81-7)

Conditions	Yield
In water; acetone for 8h; Ambient temperature;	70%

1-adamanthanol (768-95-6) + 2,4-dihydro-1,2,4-triazol-3-one (930-33-6) → 1,4-di(1-adamantyl)-1,2,4-triazol-5(1H,4H)-one

Conditions	Yield
With sulfuric acid In water at 20℃; for 26h;	70%

copper(II) nitrate trihydrate + 2,4-dihydro-1,2,4-triazol-3-one (930-33-6) → diaquadi(1,2,4-triazol-5-one)copper(II) nitrate

Conditions	Yield
In water aq. soln. of Cu-salt was added dropwise to aq. soln. of N-compd. at 70 °C in 40 min, stirring at this temp. for 20 min; cooling to room temp., slow evapn. at room temp., crystn. for about 5 weeks, elem. anal.;	65%

zinc(II) nitrate hexahydrate + 2,4-dihydro-1,2,4-triazol-3-one (930-33-6) → diaquadi(1,2,4-triazol-5-one)zinc(II) nitrate

Conditions	Yield
In methanol; water 1,2,4-triazole-5-one dissolved in H2O was dropped into soln. of Zn salt in EtOH at 60°C; mixt. stirred for about 30 min; ppt. has been leached; filtrate was left at room temp. for 20 ds to obtain single crystals; ppt. washed (anhyd. alc.) for 3 times; dried at roomtemp.; elem. anal.;	63%

2,4-dihydro-1,2,4-triazol-3-one (930-33-6) + iodoacetone (3019-04-3) → 2-(2-oxopropyl)-2,4-dihydro-3H-1,2,4-triazol-3-one (1557156-13-4)

Conditions	Yield
In dimethyl sulfoxide at 25℃;	62%

triphenylmethyl alcohol (76-84-6) + 2,4-dihydro-1,2,4-triazol-3-one (930-33-6) → C21H17N3O (895135-99-6)

Conditions	Yield
Stage #1: triphenylmethyl alcohol; 2,4-dihydro-1,2,4-triazol-3-one With toluene-4-sulfonic acid In toluene for 20h; Heating / reflux; Stage #2: With sodium hydrogencarbonate In water; toluene	60%

hydrogenchloride (7647-01-0) + cobalt(II) chloride hexahydrate + 2,4-dihydro-1,2,4-triazol-3-one (930-33-6) → [CoCl2(1,2,4-triazole-5-one)2](n)

Conditions	Yield
In ethanol; water ligand dissolved in H2O mixed with soln. of CoCl2*6H2O in EtOH at 60°C; ppt. was obtained; HCl added until solid dissolved; soln. was left at room temp. for 15 ds; crystals were obtained; elem. anal.;	48%

2-iodo-1-(thien-2-yl)ethan-1-one (55984-19-5) + 2,4-dihydro-1,2,4-triazol-3-one (930-33-6) → 4-[2-oxo-2-(2-thienyl)ethyl]-2,4-dihydro-3H-1,2,4-triazol-3-one

Conditions	Yield
In dimethyl sulfoxide at 25℃;	46%

N-(2,4-difluorophenyl)-N-isopropylcarbamoyl chloride (212203-09-3) + 2,4-dihydro-1,2,4-triazol-3-one (930-33-6) → N-(2,4-difluorophenyl)-N-isopropyl-5-oxo-1H-1,2,4-triazole-4-carboxamide

Conditions	Yield
Stage #1: 2,4-dihydro-1,2,4-triazol-3-one With potassium carbonate In N,N-dimethyl-formamide at 100℃; for 0.5h; Stage #2: N-(2,4-difluorophenyl)-N-isopropylcarbamoyl chloride In N,N-dimethyl-formamide at 25 - 100℃; for 2h;	45%

1-(1,1'-biphenyl)-4-yl-2-iodo-1-ethanone + 2,4-dihydro-1,2,4-triazol-3-one (930-33-6) → 2-[2-(1,1'-biphenyl)-4-yl-2-oxoethyl]-2,4-dihydro-3-1,2,4-triazol-3-one (1557156-15-6)

Conditions	Yield
In dimethyl sulfoxide at 25℃;	39%

benzyl chloride (100-44-7) + 2,4-dihydro-1,2,4-triazol-3-one (930-33-6) → 4-Benzyl-1,2,4-triazol-3(2H)-one (98292-37-6) + 2,4-dibenzyl-2,4-dihydro-3H-1,2,4-triazol-3-one (34773-85-8)

Conditions	Yield
With sodium methylate In N,N-dimethyl-formamide for 4.5h; Ambient temperature;	A 33% B 16%

2,4-dihydro-1,2,4-triazol-3-one (930-33-6) + 1-bromomethyl-4-bromobenzene (589-15-1) → 4-[(4-bromophenyl)methyl]-1H-1,2,4-triazol-5-one

Conditions	Yield
Stage #1: 2,4-dihydro-1,2,4-triazol-3-one With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 0.166667h; Stage #2: 1-bromomethyl-4-bromobenzene In N,N-dimethyl-formamide at 20℃; for 16h;	23.9%

N-(2,4-difluorophenyl)-N-isopropylcarbamoyl chloride (212203-09-3) + 2,4-dihydro-1,2,4-triazol-3-one (930-33-6) → N,N-bis(2,4-difluorophenyl)-N,N-diisopropyl-5-oxo-1,2,4-triazole-1,4-dicarboxamide

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 25 - 90℃; for 3h;	23%

(5R)-methanesulfonic acid 3-(3-fluoro-4-iodophenyl)-2-oxo-oxazolidin-5-ylmethyl ester (501939-82-8) + 2,4-dihydro-1,2,4-triazol-3-one (930-33-6) → (R)-3-(3-fluoro-4-iodophenyl)-5-((5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl)methyl)oxazolidin-2-one

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 90℃;	21%

di-tert-butyl dicarbonate (24424-99-5) + 2,4-dihydro-1,2,4-triazol-3-one (930-33-6) → tert-butyl 5-oxo-1,5-dihydro-4H-1,2,4-triazole-4-carboxylate

Conditions	Yield
With dmap; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 18h;	14%

5-[5-amino-4-(3-chloro-5-trifluoromethylphenyl)-3-trifluoromethylpyrazol-1-yl]-2-fluorobenzonitrile (1208348-78-0) + 2,4-dihydro-1,2,4-triazol-3-one (930-33-6) → 5-[5-amino-4-(3-chloro-5-trifluoromethylphenyl)-3-trifluoromethylpyrazol-1-yl]-2-(5-oxo-4,5-dihydro[1,2,4]triazol-1-yl)benzonitrile (1208339-62-1)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 0.25h;	12%

3-(6-bromo-3-(bromomethyl)-2-fluorophenoxy)-5-chlorobenzonitrile (1007571-61-0) + 2,4-dihydro-1,2,4-triazol-3-one (930-33-6) → 3-[6-Bromo-2-fluoro-3-(5-oxo-1,5-dihydro-[1,2,4]triazol-4-ylmethyl)-phenoxy]-5-chloro-benzonitrile (1095279-87-0)

Conditions	Yield
With potassium carbonate; potassium iodide In acetonitrile at 85℃; for 2h;	10%

Upstream product

• 4538-16-3 5-oxo-2,5-dihydro-1H-[1,2,4]triazole-3-carboxylic acid 
• 6377-59-9 N'-carbamoyl-N,N-diformyl-hydrazine 
• 4426-72-6 hydrazine carboxamide 
• 122-51-0 orthoformic acid triethyl ester 
• 110-20-3 acetone semicarbazone 
• 83490-19-1 N-Aminocarbonyl-N',N'-dimethyl-formamidin 
• 290-87-9 1,3,5-Triazine 
• 64-18-6 formic acid 
• 563-41-7 semicarbazide hydrochloride 
• 1003-35-6 5-amino-2,4-dihydro-3H-1,2,4-triazol-3-one 
• 29983-26-4 2-ethyl-2,4-dihydro-[1,2,4]triazole-3-thione 
• 537698-45-6 2-β-cyanoethyl-1,2,4-triazol-3(2H)-one 
• 149-73-5 trimethyl orthoformate 
• 61-82-5 3⁽⁵⁾-amino-1,2,4-triazole 

Downstream Products

• 114849-01-3 4-vinyl-1,2,4-triazol-3-one 
• 80049-46-3 2-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-1,2,4-triazolin-3-one 
• 80049-42-9 2,4-bis(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-1,2,4-triazolin-3-one 
• 80049-44-1 4-(2,3,5-Tri-O-benzoyl-β-D-ribofuranosyl)-1,2,4-triazol-3(2H)-one 
• 4114-43-6 4-methyl-2,4-dihydro-3H-1,2,4-triazol-3-one 
• 4114-39-0 1,2-dimethyl-3-oxo-1,2,4-triazoline 
• 7411-17-8 3-methoxy-1:2:4-triazole 
• 67103-82-6 5-methoxy-1-methyl-1H-[1,2,4]triazole 
• 4114-36-7 2,4-dimethyl-2,4-dihydro-[1,2,4]triazol-3-one 
• 35102-19-3 3-methoxy-1-methyl-1H-[1,2,4]triazole 
• 83749-87-5 2,4-bis(1-phenyl-2-cyanovinylene)-1,2,4-triazol-3-one 
• 98292-37-6 4-Benzyl-1,2,4-triazol-3(2H)-one 
• 34773-85-8 2,4-dibenzyl-2,4-dihydro-3H-1,2,4-triazol-3-one 
• 86548-94-9 1,4-diglycidyl-1,2,4-triazolone-5 

Relevant academic research and scientific papers

1,2,4-TRIAZOLINOE CB1 INHIBITORS

Disclosed are compounds according to Formula (I), and related pharmaceutical compositions. Also disclosed are therapeutic methods, e.g., of treating diseases such as diabetic kidney disease, diabetic nephropathy, obesity-related kidney disease, focal segmental glomerular sclerosis, IgA nephropathy, nephrotic syndrome, kidney fibrosis, Prader Willi syndrome, metabolic syndrome, gastrointestinal diseases, non-alcoholic liver disease, alcoholic liver disease, or non-alcoholic fatty liver disease, using the compounds of Formula (I).

PIPERAZINE CYCLIC UREAS

Provided are piperazine cyclic urea compounds that inhibit cellular necrosis and/or human receptor interacting protein 1 kinase (RIP1), pharmaceutically acceptable salts, hydrates and stereoisomers thereof. Provided are also pharmaceutical compositions, methods of making, and methods of use which include treating a person in need thereof with an effective amount of the compound or composition, and detecting a resultant improvement in the person's health or condition.

1-(N,N-DISUBSTITUTED CARBAMOYL) 4-(SUBSTITUTED SULFONYL)TRIAZOLIN-5-ONE DERIVATIVE, 4-(N,N-DISUBSTITUTED CARBAMOYL) 1-(SUBSTITUTED SULFONYL)TRIAZOLIN-5-ONE DERIVATIVE, AND HERBICIDE CONTAINING SAID DERIVATIVE AS ACTIVE INGREDIENT

The present invention provides 1-(N,N-disubstituted carbamoyl) 4-(substituted sulfonyl)triazolin-5-one derivatives represented general formula 1, and 4-(N,N-disubstituted carbamoyl) 1-(substituted sulfonyl)triazolin-5-one derivatives represented by general formula (11), which show excellent herbicidal activity, and herbicides characterized by containing the derivatives as an active ingredient. In general formula (1), R1-R4 represent predetermined substituents. In general formula (11), R11-R14 represent predetermined substituents.

Structure-activity relationships of triazole-benzodioxine inhibitors of cathepsin X

Cathepsin X is a cysteine carboxypeptidase that is involved in various physiological and pathological processes. In particular, highly elevated expression and activity of cathepsin X has been observed in cancers and neurodegenerative diseases. Previously, we identified compound Z9 (1-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-2-((4-isopropyl-4H-1,2,4-triazol-3-yl)thio)ethan-1-one) as a potent and specific reversible cathepsin X inhibitor. Here, we have explored the effects of chemical variations to Z9 of either benzodioxine or triazol moieties, and the importance of the central ketomethylenethio linker. The ketomethylenethio linker was crucial for cathepsin X inhibition, whereas changes of the triazole heterocycle did not alter the inhibitory potencies to a greater extent. Replacement of benzodioxine moiety with substituted benzenes reduced cathepsin X inhibition. Overall, several synthesized compounds showed similar or improved inhibitory potencies against cathepsin X compared to Z9, with IC50 values of 7.1 μM–13.6 μM. Additionally, 25 inhibited prostate cancer cell migration by 21%, which is under the control of cathepsin X.

METHOD FOR OBTAINING SOLUTIONS OF OTA IN A CONCENTRATED SULFURIC ACID MEDIUM; SAID SOLUTIONS; AND METHOD FOR PREPARING ONTA

A method for obtaining solutions that contain 1,2,4-triazole-5-one (OTA) in concentrated sulphuric acid, includes using 3-amino-1,2,4-triazole (ATA) as a precursor of OTA. There is also provided a method for preparing 3-nitro-1,2,4-triazole-5-one (4) (ONTA) from the solutions.

METHOD FOR OBTAINING SOLUTIONS OF OTA IN A CONCENTRATED SULFURIC ACID MEDIUM； SAID SOLUTIONS； AND METHOD FOR PREPARING ONTA

A method for obtaining solutions that contain 1,2,4-triazole-5-one (OTA) in concentrated sulphuric acid, includes using 3-amino-1,2,4-triazole (ATA) as a precursor of OTA. There is also provided a method for preparing 3-nitro-1,2,4-triazole-5-one (4) (ONTA) from the solutions.

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.

The crystal and computed structures of 1,2,4-triazol-5-one (TO)

1,2,4-Triazol-5-one (TO) was synthesized by reacting semicarbazide hydrochloride with formic acid and its single crystal was grown by the slow evaporation method. Its molecular structure and crystal structure were determined by X-ray single crystal diffraction technique. The obtained results show that the crystal belongs to Crystal system of Monoclinic, space group Pn. It was characterized by elemental microanalysis and FT-IR techniques. Based on the crystal data, we had also carried quantum chemistry calculations on the title compound using the B3LYP and MP2 method with cc-pVTZ basis set. The calculation results further demonstrate the crystal structure of title compound and its other related properties.

Process for the preparation of 1,2,4- triazolin-5-one derivatives

The present invention relates to a process for the preparation of a compound of formula (I) wherein R represents hydrogen, C1-10alkyl, haloC1-10alkyl or aryl; which are useful intermediates in the preparation of morpholine derivatives of formula (A). Compounds of formula (A) are useful as therapeutic agents.