96240-10-7

Usage

Uses

Used in Pharmaceutical Industry:
4-Amino-2,4-dihydro-5-(1-methylethyl)-3H-1,2,4-triazol-3-one is used as an intermediate in the synthesis of pharmaceutical compounds. Its unique structure allows it to be a key component in the development of new drugs with potential therapeutic applications.
Used in Agrochemical Industry:
4-Amino-2,4-dihydro-5-(1-methylethyl)-3H-1,2,4-triazol-3-one is used as an important intermediate for herbicide amicarbazone preparation. Its presence in the synthesis process contributes to the development of effective herbicides that help control unwanted plant growth in agricultural settings.
Used in Chemical Research:
4-Amino-2,4-dihydro-5-(1-methylethyl)-3H-1,2,4-triazol-3-one is utilized in chemical research for studying the properties and reactions of triazole compounds. Its unique structure makes it a valuable subject for exploring new chemical reactions and potential applications in various fields.

InChI:InChI=1/C5H10N4O/c1-3(2)4-7-8-5(10)9(4)6/h3H,6H2,1-2H3,(H,8,10)

Synthetic route

C8H16N2O3 → 4-amino-3-isopropyl-1H-1,2,4-triazol-5-(4H)-one (96240-10-7)

Conditions	Yield
With hydrazine hydrate; potassium hydroxide In water; toluene at 100 - 110℃; pH=7 - 7.5; Dean-Stark;	95.1%

N'-Isobutyryl-hydrazinecarboxylic acid methyl ester → 4-amino-3-isopropyl-1H-1,2,4-triazol-5-(4H)-one (96240-10-7)

Conditions	Yield
With hydrazine hydrate; sodium hydroxide In water; toluene at 100 - 110℃; Reagent/catalyst; Dean-Stark;	91.4%
With hydrazine hydrate; sodium hydroxide In water; toluene at 100 - 110℃; Dean-Stark;	91.4%

5-isopropyl-3H-[1,3,4]oxadiazol-2-one (1711-88-2) + butan-1-ol (71-36-3) → 4-amino-3-isopropyl-1H-1,2,4-triazol-5-(4H)-one (96240-10-7)

Conditions	Yield
With hydrogenchloride; sodium hydroxide; hydrazine hydrate In water	89.3%
With sodium hydroxide; hydrazine hydrate In ice-water; water	79%

C7H14N2O3 → 4-amino-3-isopropyl-1H-1,2,4-triazol-5-(4H)-one (96240-10-7)

Conditions	Yield
With hydrazine hydrate; potassium hydroxide In water; toluene at 100 - 110℃; Dean-Stark;	89.3%

C9H18N2O3 → 4-amino-3-isopropyl-1H-1,2,4-triazol-5-(4H)-one (96240-10-7)

Conditions	Yield
With sodium carbonate; hydrazine hydrate at 95 - 100℃; for 3h; Temperature; Reagent/catalyst;	85.3%

carbonodihydrazide (497-18-7) + n-butyl isobutyrate (97-87-0) → 4-amino-3-isopropyl-1H-1,2,4-triazol-5-(4H)-one (96240-10-7)

Conditions	Yield
Stage #1: carbonodihydrazide With potassium carbonate In N,N-dimethyl-formamide Reflux; Stage #2: n-butyl isobutyrate In N,N-dimethyl-formamide at 140 - 145℃; for 5h;	76.8%

carbonodihydrazide (497-18-7) + Ethyl isobutyrate (97-62-1) → 4-amino-3-isopropyl-1H-1,2,4-triazol-5-(4H)-one (96240-10-7)

Conditions	Yield
Stage #1: carbonodihydrazide With potassium carbonate In ethanol Reflux; Stage #2: Ethyl isobutyrate In ethanol at 70 - 75℃; for 4h;	75.2%

carbonodihydrazide (497-18-7) + isobutyric Acid (79-31-2) → 4-amino-3-isopropyl-1H-1,2,4-triazol-5-(4H)-one (96240-10-7)

Conditions	Yield
Stage #1: carbonodihydrazide; isobutyric Acid With potassium carbonate In water at 60 - 65℃; for 5h; Stage #2: With sodium hydroxide In water at 60 - 65℃; for 3h; Reagent/catalyst; Temperature; Solvent;	74.8%

Methyl isobutyrate (547-63-7) + carbonodihydrazide (497-18-7) → 4-amino-3-isopropyl-1H-1,2,4-triazol-5-(4H)-one (96240-10-7)

Conditions	Yield
Stage #1: carbonodihydrazide With lithium hydroxide In toluene Reflux; Stage #2: Methyl isobutyrate In toluene at 105 - 110℃; for 4h;	73.1%

N'-[1-Ethoxy-2-methyl-prop-(E)-ylidene]-hydrazinecarboxylic acid ethyl ester → 4-amino-3-isopropyl-1H-1,2,4-triazol-5-(4H)-one (96240-10-7)

Conditions	Yield
With hydrazine hydrate In butan-1-ol for 30h; Heating;

bis(phenyl) carbonate (102-09-0) + Isobutyronitrile (78-82-0) + carbonodihydrazide (497-18-7) + dimethyltin oxide (2273-45-2) + diethylamine (109-89-7) → 4-amino-3-isopropyl-1H-1,2,4-triazol-5-(4H)-one (96240-10-7)

Conditions	Yield
With hydrazine hydrate In water; phenol

5-isopropyl-3H-[1,3,4]oxadiazol-2-one (1711-88-2) → 4-amino-3-isopropyl-1H-1,2,4-triazol-5-(4H)-one (96240-10-7)

Conditions	Yield
With hydrazine hydrate; sodium hydroxide at 90 - 110℃; for 4h; Temperature;

4-amino-3-isopropyl-1H-1,2,4-triazol-5-(4H)-one (96240-10-7) + Tert-butyl isocyanate (1609-86-5) → amicarbazone (129909-90-6)

Conditions	Yield
With potassium hydroxide; lithium chloride In acetic acid methyl ester	96%
With potassium hydroxide In toluene at 60℃; for 0.5h; Dean-Stark;	95%
With potassium hydroxide; lithium chloride In acetic acid methyl ester	94%
With 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at 20℃; for 2h;
With lithium chloride; potassium hydroxide In ethyl acetate at 70℃; for 2.5h; Temperature;

4-amino-3-isopropyl-1H-1,2,4-triazol-5-(4H)-one (96240-10-7) + ethyl bromoacetate (105-36-2) → (4-Amino-3-isopropyl-5-oxo-4,5-dihydro-[1,2,4]triazol-1-yl)-acetic acid ethyl ester (96240-13-0)

Conditions	Yield
With sodium hydride 1)DMF, room temp., 30 min, 70-80deg C, 2h 2)70-80 deg C, 8h; Yield given. Multistep reaction;

4-amino-3-isopropyl-1H-1,2,4-triazol-5-(4H)-one (96240-10-7) + ethylene dibromide (106-93-4) → 4-Amino-2-(2-bromo-ethyl)-5-isopropyl-2,4-dihydro-[1,2,4]triazol-3-one (96240-24-3)

Conditions	Yield
With sodium hydride 1)DMF, room temp., 30 min, 70-80deg C, 2h 2)70-80 deg C, 8h; Yield given. Multistep reaction;

4-amino-3-isopropyl-1H-1,2,4-triazol-5-(4H)-one (96240-10-7) → 4-Amino-5-isopropyl-2-(2-mercapto-ethyl)-2,4-dihydro-[1,2,4]triazol-3-one (96251-97-7)

Conditions	Yield
Multi-step reaction with 3 steps 1: NaH / 1)DMF, room temp., 30 min, 70-80deg C, 2h 2)70-80 deg C, 8h 2: Na2S2O3 / aq. ethanol / 12 h / Heating 3: conc.HCl / ethanol / 1 h / Heating View Scheme

4-amino-3-isopropyl-1H-1,2,4-triazol-5-(4H)-one (96240-10-7) → C7H13N4O4S2(1-)*Na(1+)

Conditions	Yield
Multi-step reaction with 2 steps 1: NaH / 1)DMF, room temp., 30 min, 70-80deg C, 2h 2)70-80 deg C, 8h 2: Na2S2O3 / aq. ethanol / 12 h / Heating View Scheme

cyclopentyl isocyanate (4747-71-1) + 4-amino-3-isopropyl-1H-1,2,4-triazol-5-(4H)-one (96240-10-7) → 4-amino-1-(N-cyclopentylcarbamoyl)-3-isopropyl-1,2,4-triazolin-5-one (129909-73-5)

Conditions	Yield
With diaza-bicyclo-undecene In dichloromethane; acetonitrile
With diaza-bicyclo-undecene In dichloromethane; acetonitrile
With diaza-bicyclo-undecene In dichloromethane; acetonitrile

2-methyl-4-(2-chlorophenyl)-but-2-yl isocyanate (146852-01-9) + 4-amino-3-isopropyl-1H-1,2,4-triazol-5-(4H)-one (96240-10-7) → 4-amino-3-isopropyl-1-[2-methyl-4-(2-chlorophenyl)-but-2-yl-aminocarbonyl]-1,2,4-triazolin-5-one (146850-49-9)

Conditions	Yield
With diaza-bicyclo-undecene In acetonitrile

Upstream product

• 102-09-0 bis(phenyl) carbonate 
• 78-82-0 Isobutyronitrile 
• 497-18-7 carbonodihydrazide 
• 2273-45-2 dimethyltin oxide 
• 109-89-7 diethylamine 
• 1711-88-2 5-isopropyl-3H-[1,3,4]oxadiazol-2-one 
• 79-31-2 isobutyric Acid 
• 547-63-7 Methyl isobutyrate 
• 97-62-1 Ethyl isobutyrate 
• 97-87-0 n-butyl isobutyrate 
• 71-36-3 butan-1-ol 

Downstream Products

• 146850-49-9 4-amino-3-isopropyl-1-[2-methyl-4-(2-chlorophenyl)-but-2-yl-aminocarbonyl]-1,2,4-triazolin-5-one 
• 129909-90-6 amicarbazone 

Relevant academic research and scientific papers

Preparation method of 4-amino-3-isopropyl-1, 2, 4-triazoline-5-ketone

The invention relates to a preparation method of 4-amino-3-isopropyl-1, 2, 4-triazole-5-ketone. The preparation method comprises the step that under the action of alkali, carbohydrazide and a compoundA react at the temperature ranging from -15 DEG C to 150 DEG C to generate 4-amino-3-isopropyl-1, 2, 4-triazoline-5-ketone, wherein the compound A is isobutyric acid or isobutyrate, and the alkali isone or more of sodium hydroxide, potassium hydroxide, lithium hydroxide, calcium hydroxide, sodium carbonate, potassium carbonate and lithium carbonate. The purity of the 4-amino-3-isopropyl-1, 2, 4-triazoline-5-ketone prepared through the step is 97% or above, and the total yield of the 4-amino-3-isopropyl-1, 2, 4-triazoline-5-ketone is 72% or above. The method is safer and more environment-friendly, avoids the use of toxic reagents and the generation of a large amount of acidic wastewater or waste gas, has the advantages of simple and efficient process route, low requirements on productionequipment and high purity of the obtained product, greatly enhances the production safety, and is easy for industrial popularization.

Method for preparing 3-isopropyl-4-amino-1,2,4-triazoline-5-ketone

The invention discloses a method for preparing 3-isopropyl-4-amino-1,2,4-triazoline-5-ketone. The method comprises the following steps: 1, reacting isobutyric acid and hydrazine hydrate in an n-butylalcohol solvent at the reaction temperature of 50-150 DEG C, and producing isobutyrohydrazide; 2, reacting the isobutyrohydrazide synthesized in the step 1 and phosgene or solid light and the n-butylalcohol serving as the solvent at the reaction temperature of 0-60 DEG C, and producing 2-isobutyl hydrazino-butyl formate; 3, reacting the 2-isobutyl hydrazino-butyl formate synthesized in the step 2with hydrazine hydrate in aqueous alkali at a reaction temperature of 80-120 DEG C, thereby obtaining the 3-isopropyl-4-amino-1,2,4-triazoline-5-ketone and n-butyl alcohol. According to the method disclosed by the invention, single n-butyl alcohol serves as the solvent in the whole reaction process, the intermediate process is not separated, and the method has the advantages of being simple in reaction system, high in reaction speed and less in amount of three wastes; the n-butyl alcohol can be repeatedly used; and the synthetic method has the yield of 85%.

Amicarbazone synthesis method

The invention discloses an amicarbazone synthesis method, which comprises: synthesizing tert-butyl isocyanate; synthesizing 5-methyl-1,3,4-oxadiazol-2(3H)-one; synthesizing 4-amino-3-isopropyl-5-oxo-1-H-1,2,4-triazole (triazolinone); adding hydrazine hydrate and a second NaOH solution to a third reactor, uniformly stirring, heating to a temperature of 90-100 DEG C, adding the prepared 5-methyl-1,3,4-oxadiazol-2(3H)-one in a dropwise manner, carrying out a reaction after completing the adding, cooling to a room temperature, adding a second solvent, adjusting the pH value to a neutral pH value, freezing for 2-2.5 h, filtering, washing the filter cake, re-crystallizing, and drying to obtain triazolinone; and synthesizing the amicarbazone, wherein triazolinone, potassium hydroxide, a second catalyst and a third solvent are added to a fourth reactor, the prepared tert-butyl isocyanate is added in a dropwise manner, and a heating reaction is performed to obtain the amicarbazone. According to the present invention, the synthesis method has advantages of mild reaction conditions, no requirement of special equipment, good economy, high total yield and good industrial prospect.

METHOD FOR PREPARING AMICARBAZONE

The present invention relates to a method for preparing amicarbazone by using amino-triazolinone, which is an intermediate compound, and relates to a method for preparing amicarbazone, comprising the steps of: obtaining hydrazine carboxylic acid represented by 5 chemical formula (V) by reacting acylhydrazide represented by chemical formula (II) and a carbamating agent represented by chemical formula (III) or (IV); reacting the obtained hydrazine carboxylic acid represented by chemical formula (V) and hydrazine hydrate in the presence of a base catalyst; and reacting the obtained compound represented by chemical formula (I) 10 and an alkyl isocyanate represented by chemical formula (IV) in the presence of a base catalyst. Amino-triazolinone and amicarbazone would be stably produced by the present invention without safety gear and safety facilities for the leakage of phosgene, which has been conventionally used as a reactant.

METHOD FOR PREPARING AMINO-TRIAZOLINONE

The present invention relates to a method for preparing an amino-triazolinone which can be used as a raw material for amicarbazone and has chemical formula (I). The method for preparing the amino-triazolinone includes the steps of: reacting an acyl hydrazide of chemical formula (II) with a carbamating agent of chemical formula (III) or (IV) so as to obtain a hydrazine carboxylic acid of chemical formula (V); and reacting the thus-obtained hydrazine carboxylic acid of chemical formula (V) with a hydrazine hydrate under the presence of a base catalyst. According to the present invention, the amino-triazolinone may be stably prepared without using safety equipment or safety facilities for a possible leakage of phosgene, which has been used as a conventional reactant. Thus, manufacturing costs for amicarbazone, which is used as a herbicide for farm products such as sugar cane, corn, or the like, can be reduced so as to achieve improved price competitiveness, and further to achieve improved cost competitiveness compared to other herbicides.

Process for the preparation of substituted aminotriazolinones

The invention relates to a new process for the preparation of substituted aminotriazolinones of the general formula (I) STR1 in which R has the meanings mentioned in the description.

Preparation of 4-amino-1,2,4-triazol-5-ones

A process for the preparation of 4-amino-1,2,4-triazol-5-one of the formula STR1 in which p0 R represents unsubstituted or substituted alkyl, alkenyl, cycloalkenyl, cycloalkyl, aralkyl, aryl or heterocyclyl, which comprises reacting a carbodihydrazide of the formula STR2 with a nitrile of the formula The carbodihydrazide of the formula (II) may be produced in a preliminary stage by reacting a carbonic acid derivative with hydrazine or hydrazine hydrate.