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[ CAS No. 96240-10-7 ] {[proInfo.proName]}

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Chemical Structure| 96240-10-7
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Product Details of [ 96240-10-7 ]

CAS No. :96240-10-7 MDL No. :MFCD04972517
Formula : C5H10N4O Boiling Point : -
Linear Structure Formula :- InChI Key :JIXOMCFZRAAWKK-UHFFFAOYSA-N
M.W : 142.16 Pubchem ID :10866435
Synonyms :

Calculated chemistry of [ 96240-10-7 ]

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 5
Fraction Csp3 : 0.6
Num. rotatable bonds : 1
Num. H-bond acceptors : 2.0
Num. H-bond donors : 2.0
Molar Refractivity : 37.57
TPSA : 76.7 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -7.4 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.04
Log Po/w (XLOGP3) : -0.33
Log Po/w (WLOGP) : -0.58
Log Po/w (MLOGP) : -0.01
Log Po/w (SILICOS-IT) : -0.21
Consensus Log Po/w : -0.02

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -0.82
Solubility : 21.6 mg/ml ; 0.152 mol/l
Class : Very soluble
Log S (Ali) : -0.82
Solubility : 21.5 mg/ml ; 0.152 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -0.38
Solubility : 58.9 mg/ml ; 0.414 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.19

Safety of [ 96240-10-7 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P301+P312-P302+P352-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 96240-10-7 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 96240-10-7 ]

[ 96240-10-7 ] Synthesis Path-Downstream   1~19

  • 1
  • N'-[1-Ethoxy-2-methyl-prop-(E)-ylidene]-hydrazinecarboxylic acid ethyl ester [ No CAS ]
  • [ 96240-10-7 ]
YieldReaction ConditionsOperation in experiment
With hydrazine hydrate In butan-1-ol for 30h; Heating;
  • 2
  • [ 96240-10-7 ]
  • [ 105-36-2 ]
  • [ 96240-13-0 ]
YieldReaction ConditionsOperation in experiment
With sodium hydride 1)DMF, room temp., 30 min, 70-80deg C, 2h 2)70-80 deg C, 8h; Yield given. Multistep reaction;
  • 3
  • [ 96240-10-7 ]
  • [ 106-93-4 ]
  • [ 96240-24-3 ]
YieldReaction ConditionsOperation in experiment
With sodium hydride 1)DMF, room temp., 30 min, 70-80deg C, 2h 2)70-80 deg C, 8h; Yield given. Multistep reaction;
  • 4
  • [ 96240-10-7 ]
  • [ 96251-97-7 ]
YieldReaction ConditionsOperation in experiment
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
  • 5
  • [ 96240-10-7 ]
  • C7H13N4O4S2(1-)*Na(1+) [ No CAS ]
YieldReaction ConditionsOperation in experiment
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
  • 6
  • [ 4747-71-1 ]
  • [ 96240-10-7 ]
  • [ 129909-73-5 ]
YieldReaction ConditionsOperation in experiment
With diaza-bicyclo-undecene In dichloromethane; acetonitrile 164 EXAMPLE 164 STR396 EXAMPLE 164 STR396 6.1 g (0.055 mol) of cyclopentyl isocyanate and a small amount of diazabicycloundecene (DBU) are added to 7.1 g (0.05 mol) of 4-amino-3-isopropyl-(1H)-1,2,4-triazolin-5-one in 100 ml of absolute acetonitrile, the mixture is stirred for 12 hours at room temperature and then concentrated in vacuo, the residue is taken up in dichloromethane, the solution is washed with water to neutrality, dried over magnesium sulphate and concentrated, and the residue is crystallized by trituration with diethyl ether. 10.0 g (78% of theory) of 4-amino-1-(N-cyclopentylcarbamoyl)-3-isopropyl-1,2,4-triazolin-5-one of melting point 109° C. are obtained.
With diaza-bicyclo-undecene In dichloromethane; acetonitrile 164 Example 164 STR418 (process (b)) 6.1 g (0.055 mol) of cyclopentyl isocyanate and a small amount of diazabicycloundecene (DBU) are added to 7.1 g (0.05 mol) of 4-amino-3-isopropyl-(1H)-1,2,4-triazolin-5-one in 100 ml of absolute acetonitrile, the mixture is stirred for 12 hours at room temperature and then concentrated in vacuo, the residue is taken up in dichloromethane, the solution is washed with water to neutrality, dried over magnesium sulphate and concentrated, and the residue is crystallized by trituration with diethyl ether. 10.0 g (78% of theory) of 4-amino-1-(N-cyclopentylcarbamoyl)-3-isopropyl-1,2,4-triazolin-5-one of melting point 109° C. are obtained.
With diaza-bicyclo-undecene In dichloromethane; acetonitrile 164 Example 164 (process (b)) 6.1 g (0.055 mol) of cyclopentyl isocyanate and a small mount of diazabicycloundecene (DBU) are added to 7.1 g (0.05 mol) of 4-amino-3-isopropyl-(1H)-1,2,4-triazolin-5-one in 100 ml of absolute acetonitrile, the mixture is stirred for 12 hours at room temperature and then concentrated in vacuo, the residue is taken up in dichloromethane, the solution is washed with water to neutrality, dried over magnesium sulphate and concentrated, and the residue is crystallized by trituration with diethyl ether. 10.0 g (78% of theory) of 4-amino-1-(N-cyclopentylcarbamoyl)-3-isopropyl-1,2,4-triazolin-5-one of melting point 109° C. are obtained.
  • 7
  • [ 146852-01-9 ]
  • [ 96240-10-7 ]
  • [ 146850-49-9 ]
YieldReaction ConditionsOperation in experiment
With diaza-bicyclo-undecene In acetonitrile I.3 Example I-3 (Process b) To 1.4 g (0.01 mol) of 4-amino-3-isopropyl-1,2,4-triazolin-5-one (compare, for example, DE-OS (German Published Specification) 3,803,523) in 100 ml of acetonitrile there are added 1 ml of diazabicycloundecene (DBU) and 2.2 g (0.01 mol) of 2-methyl-4-(2-chlorophenyl)-but-2-yl isocyanate, the mixture is subsequently stirred for 18 hours at 40° C. and then cooled to room temperature, and the product which has been obtained in crystalline form is filtered off. 1.4 g (38 % of theory) of 4-amino-3-isopropyl-1-[2-methyl-4-(2-chlorophenyl)-but-2-yl-aminocarbonyl]-1,2,4-triazolin-5-one of melting point 159° C. are obtained.
  • 8
  • [ 1711-88-2 ]
  • [ 71-36-3 ]
  • [ 96240-10-7 ]
YieldReaction ConditionsOperation in experiment
89.3% With hydrogenchloride; sodium hydroxide; hydrazine hydrate In water 2 EXAMPLE 2 STR6 EXAMPLE 2 STR6 118.4 g (0.914 mol) of 5-i-propyl-1,3,4-oxadiazol-2(3H)-one are added dropwise with stirring in the course of about 25 minutes to a mixture, heated to 102° C. to 105° C., of 45.8 g (0.915 mol) of hydrazine hydrate, 12.2 g of 45% strength sodium hydroxide solution (0.137 mol of NaOH) and 460 ml of n-butanol and the reaction mixture is then kept in the temperature range between 100° C. and 105° C. for 3 hours. After cooling to about 20° C., it is diluted with 100 ml of water and adjusted to pH 7 using 33% strength hydrochloric acid. After addition of a further 200 ml of water, a clear two-phase mixture of butanol and water is obtained. By continuous extraction of the water phase with butanol at 80° C., all the reaction product can be collected in the organic phase, while the by-products formed in the reaction remain in the water. By distilling off the butanol, 118 g (purity: 98.3%, i.e. yield 89.3% of theory) of 4-amino-5-i-propyl-2,4-dihydro-3H-1,2,4-triazol-3-one of melting point 171° C. are obtained.
79% With sodium hydroxide; hydrazine hydrate In ice-water; water 1 EXAMPLE 1 STR5 EXAMPLE 1 STR5 118.4 g (0.914 mol) of 5-i-propyl-1,3,4-oxadiazol-2(3H)-one are added dropwise with stirring in the course of about 25 minutes to a mixture, heated to 102° C. to 105° C., of 45.8 g (0.915 mol) of hydrazine hydrate, 12.2 g of 45% strength sodium hydroxide solution (0.137 mol of NaOH) and 460 ml of n-butanol and the reaction mixture is then kept in the temperature range between 100° C. and 105° C. for 3 hours. After cooling to about 50° C., it is diluted with 230 ml of water and the pH is then adjusted to 7 at about 20° C. by addition of about 45% strength sulphuric acid. The solvent is then largely distilled off, first at normal pressure, then at a pressure between 100 mbar and 110 mbar (bath temperature: about 60° C.), the residue which remains is dissolved in 230 ml of water at about 75° C., and the solution is cooled to 10° C. to 20° C. The product which is obtained in crystalline form in this process is isolated by filtering off, washed with 20 ml of ice-water and dried in a water-jet vacuum at 60° C. 105 g (purity: 98%, i.e. yield: 79% of theory) of 4-amino-5-i-propyl-2,4-dihydro-3H-1,2,4-triazol-3-one of melting point 171° C. are obtained.
  • 9
  • [ 96240-10-7 ]
  • [ 1609-86-5 ]
  • [ 129909-90-6 ]
YieldReaction ConditionsOperation in experiment
96% With potassium hydroxide; lithium chloride In acetic acid methyl ester 2 EXAMPLE 2 STR6 EXAMPLE 2 STR6 In the come of approximately 12 minutes, 21.8 g (0.22 moo of t-butyl isocyanate are added dropwise with stirring to a mixture, heated to 55° C. to 60° C., of 30.2 g (0.20 mol) of 4-amino-5-i-propyl-2,4-dihydro-3H- 1,2,4-triazol-3-one (purity 94.2%), 0.32 g of potassium hydroxide flakes (purity 88%), 0.20 g of lithium chloride and 200 ml of methyl acetate, and the reaction mixture is then refluxed for 3 hours. After the mixture has been cooled to approximately 20° C., the solvent is carefully removed from the filtrate by distillation under a water pump vacuum, and the residue which remains is dried under a water pump vacuum at approximately 60° C. 51.8 g (content: 93.9%, i.e. yield: 96% of theory) of 4-amino-5-i-propyl-2-t-butyl-aminocarbonyl-2,4-dihydro-3H-1,2,4-triazol-3-one of a melting range of 158° C. to 162° C. are obtained.
95% With potassium hydroxide In toluene at 60℃; for 0.5h; Dean-Stark; 11 Preparation ofAmicarbazone Using Intermediate of Example8 50 g of amino-triazolinone prepared in Example 8 and 220 g (about 250 ml) of toluene were mixed with stirring in a Dean-Stark reactor equipped with a stirrer, a reflux condenser and a thermometer, followed by adding 0.4 g of KOH (45%) thereto with stirring. Then, the reactor was heated and refluxed to remove water therefrom. Afier sufficient removal of water from the reactor, the interior temperature of the reactor was cooled to 60° C. and t-butyl isocyanate (TBIC) was added to the reactor using a dropping thnnel over about 30 minutes.10065] After completion of the reaction, the resulting material was cooled to 50° C. and neutralized with acid. The obtained product was slowly cooled to be crystallized. Here, in order to improve yield, the product was cooled to about -5° C. to 0°C. to be sufficiently crystallized, followed by filtering and drying, thereby preparing amicarbazone (yield: 95%, purity: 99.3% (HPLC)).
94% With potassium hydroxide; lithium chloride In acetic acid methyl ester 1 EXAMPLE 1 STR5 EXAMPLE 1 STR5 Within approximately 20 minutes, 54.5 g (0.55 mol) of t-butyl isocyanate are added dropwise with stirring to a mixture, heated to 55° C. to 60° C., of 72.8 g (0.50 mol) of 4-amino-5-i-propyl-2,4-dihydro-3H-1,2,4-triazol-3-one (purity 97.6%), 0.8 g of potassium hydroxide flakes (purity 88%), 0.5 g of lithium chloride and 500 ml of methyl acetate, and the reaction mixture is then refluxed for 3 hours. After the mixture has cooled to approximately 20° C., it is filtered, the solvent is carefully removed from the filtrate by distillation under a water pump vacuum, and the residue which remains is dried under a water pump vacuum at approximately 60° C. 122 g (content: 93.2%, i.e. yield: 94% of theory) of 4-amino-5-i-propyl-2-t-butyl-aminocarbonyl-2,4-dihydro-3H-1,2,4-triazol-3-one of a melting range of 158° C. to 162° C. are obtained.
94.6% Stage #1: 3-isopropyl-4-amino-1,2,4-triazolin-5-one With lithium hydroxide monohydrate In acetonitrile at 60℃; for 0.5h; Inert atmosphere; Stage #2: 2-isocyanato-2-methylpropane In acetonitrile for 1h; Inert atmosphere; 1-2; 1-4 Example 2 Under the protection of nitrogen flow, 360.00g of acetonitrile, 0.71g (0.030mol) of powdered lithium hydroxide and 71.80g (0.500mol) of powdered lithium hydroxide were sequentially put into the reaction flask 3-Isopropyl-4-amino-1,2,4-triazolin-5-one. Turn on stirring, The temperature was raised to 60°C, and 57.29 g (0.575 mol) were added in 30 minutes. Tert-butyl isocyanate was added dropwise to the reaction solution, followed by holding for 60 minutes. After the completion of the reaction, 6.00 g of acetic acid was added to neutralize the alkali in the reaction system, Sampling for HPLC analysis, the reaction conversion rate was 97.8%, The reaction selectivity was 98.7%. After concentrating and desolvating under negative pressure, add 175ml of water, stir, Cool to 10°C and filter. The filter cake was dried to obtain 116.78g of amicarbazone, The form is a white powdery solid with a purity of 97.7% and a yield of 94.6%.
With 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at 20℃; for 2h; 1 Example 1 Preparation of amorphous amicarbazone in accordance with the disclosure of in the example 2 of U.S. Pat. No. U.S. PATENT NO. 5,194,085 with modification 3.6 g (0.036 mol) of t-butyl isocyanate and 0.05 g to 0.1 g of 1 8-diazabicycloundecene (DBU) were added to 3.52 g (0.03 mol) of 4-amino-3-isopropyl-lH-1 2 4-triazol-5- (4H) -one in 80 ml of absolute acetonitrile the mixture was stirred for 2 hours at 20 concentrated in vacuo and the residue taken up in dichloromethane the solution was washed with water dried over sodium sulphate and concentrated in vacuo and the residue was precipitated as an amorphous solid by trituration with diethyl ether having a melting point of 108 in accordance with US 5,194,085.[0099][0100]Scheme 1. Synthesis of Amicarbazone[0101]As shown in Figure 4 the X-ray powder diffraction pattern of the resulting amicarbazone product has no significant signals which indicates the amicarbazone product prepared in accordance with the disclosure of in U.S. Pat. No. 5,194,085 is amorphous.
With lithium chloride; potassium hydroxide In ethyl acetate at 70℃; for 2.5h; 1.4 (4) Synthesis of amicarbazone: The triazolone, potassium hydroxide, lithium chloride catalyst and ethyl acetate were added to the fourth reactor, the prepared terbutyl isocyanate was added dropwise, heated to 70 ° C for 2.5 h, cooled to room temperature after the reaction , The filtrate was filtered and the solvent was removed and dried to obtain the mass ratio of oxazolone, triazolinone, potassium hydroxide, lithium chloride catalyst, ethyl acetate and t-butyl isocyanate: 143: 1.5: 1: 900 : 105The
With potassium hydroxide In toluene at 185℃; for 2h; 1-2; 1-2 i. Weight the required amount of Toluene, TAZ and Potassium hydroxide and put it under stirring into the 4-Neck Flask;ii. Drying (azeotropic drying (through the distillation column)) of TAZ under vacuum of 167 mmHg under controlled temperature between 61 to 67° C. until get the moisture level of 0.04% in the toluene;iii. Raise the temperature inside the flask and keep at 60° C. (±1° C.);iv. Increase agitation and add slowly and in constant flow in 30 minutes the required amount of TBIC undistilled in order to have 18% molar excess in relation to TAZ amount;v. Raise the temperature inside the flask slowly and in constantly heating to 70° C. (1° C.) in 10 min and keep it for 5 minutes;vi. Cool down the temperature slowly and in constantly inside the flask until 50° C. (1° C.) in 10 minutes and keep it;vii. Adding seed of Amicarbazone and keep stirring for 10 min;viii. Stop stirring and cool down the temperature inside the flask until 10° C. in 2 hours;ix. Filter the product formed and wash the crystals with the required amount of water;x. Dry the crystals under vacuum (200-400 mmHg) at 35-40° C. until get maximum 0.30% of moisture;xi. Assay the crystals using the specific method.

  • 10
  • [ 102-09-0 ]
  • [ 78-82-0 ]
  • [ 497-18-7 ]
  • [ 2273-45-2 ]
  • [ 109-89-7 ]
  • [ 96240-10-7 ]
YieldReaction ConditionsOperation in experiment
With hydrazine hydrate In water; phenol 7 Compound No. I-2 STR13 Analogously to Example 3, a solution of carbodihydrazide in phenol is prepared from 2,264 g (10.6 mol) of diphenyl carbonate and 1,058 g (21.2 mol) of hydrazine hydrate and is substantially dehydrated under reduced pressure. After addition of 1 g of dimethyltin oxide and 803 g (11.6 mol) of isobutyronitrile, the mixture is heated under reflux for 10 hours (initial temperature 138° C., final temperature 185° C.). The volatile components are then distilled off under reduced pressure and the residue is dissolved in 1.5 L of hot water. 116 g (1.6 mol) of diethylamine are added at 80° C. and the amine which has not been consumed and residual phenol are then distilled off. After cooling to 10° C., the product is filtered off with suction, washed with cold water and dried. 1,129 g (75% of theory) of 3-isopropyl-4-amino-1,2,4-triazol-5-one of melting point 172° C. are obtained.
  • 11
  • N'-Isobutyryl-hydrazinecarboxylic acid methyl ester [ No CAS ]
  • [ 96240-10-7 ]
YieldReaction ConditionsOperation in experiment
91.4% With hydrazine hydrate; sodium hydroxide In water; toluene at 100 - 110℃; Dean-Stark; 7 Preparation of Amino-Triazolinone as Final Product Using Toluene/NaOH EXAMPLE 7 Preparation of Amino-Triazolinone as Final Product Using Toluene/NaOH 160 g (1.0 mole) of the intermediate product (hydrazidecarboxylic acid) prepared by Example 1, 300 ml of toluene, 51 g (1.0 mole) of hydrazine hydride, 0.15 mole of NaOH (45% aqueous solution) were added to a four-neck flask reactor equipped with a Dean-Stark trap, and the obtained mixture was reflux-reacted at a reaction temperature of 100 to 110° C. and water produced as a side-product was removed. When it was not observed that water was removed, the reaction was completed, followed by cooling a temperature of the reactant to room temperature and water was added to the reactant, and the reactant was crystallized at 10° C. Then, after the crystallized product was neutralized (pH=7˜7.5) with sulfuric acid, followed by filtration, the obtained cake was washed with water and dried to obtain a product 130g (yield 91.4%, purity 98% (by GC), and melting point: 171.54° C.). shows H-NMR data of the final product obtained by Example 7. It could be appreciated that the analysis data was the same as a data of a standard intermediate (hydrazine carboxylic acid). In addition, shows differential scanning calorimetry (DSC) (thermal analysis) data for confirming a melting point of the final product obtained by Example 7. It could be appreciated from the thermal analysis data that the melting point of the obtained intermediate was 171.54° C.
91.4% With hydrazine hydrate; sodium hydroxide In water; toluene at 100 - 110℃; Dean-Stark; 7 Preparation of Amino-Triazolinone Using Toluene/NaOH 160 g (1.0 mole) of the intermediate (hydrazine carboxylic acid) prepared in Example 1, 300 ml of toluene, 51 g (1.0 mole) of hydrazine hydrate, and 0.15 mole of NaOH (45% aqueous solution) were added to a four-neck flask reactor equipped with a Dean-Stark trap, and the obtained mixture was refluxed at a reaction temperature of 100° C. to 110° C. while removing water produced as a side product. When there was no more water to be removed, the reaction was completed, followed by cooling the resulting material to room temperature while adding water to the resulting material, which in turn was crystallized at 10° C. Then, the crystallized product was neutralized (pH=7-7.5) with sulfuric acid and filtered, followed by washing the obtained cake with water and drying, thereby preparing 130 g of a product (yield: 91.4%, purity: 98% (by GC), melting point: 171.54° C.).
  • 12
  • C7H14N2O3 [ No CAS ]
  • [ 96240-10-7 ]
YieldReaction ConditionsOperation in experiment
89.3% With hydrazine hydrate; potassium hydroxide In water; toluene at 100 - 110℃; Dean-Stark; 8 Preparation of Amino-Triazolinone Using Toluene/NaOH 160 g (1.0 mole) of the intermediate (hydrazine carboxylic acid) prepared in Example 1, 300 ml of toluene, 51 g (1.0 mole) of hydrazine hydrate, and 0.15 mole of NaOH (45% aqueous solution) were added to a four-neck flask reactor equipped with a Dean-Stark trap, and the obtained mixture was refluxed at a reaction temperature of 100° C. to 110° C. while removing water produced as a side product. When there was no more water to be removed, the reaction was completed, followed by cooling the resulting material to room temperature while adding water to the resulting material, which in turn was crystallized at 10° C. Then, the crystallized product was neutralized (pH=7-7.5) with sulfuric acid and filtered, followed by washing the obtained cake with water and drying, thereby preparing 130 g of a product (yield: 91.4%, purity: 98% (by GC), melting point: 171.54° C.).
  • 13
  • C8H16N2O3 [ No CAS ]
  • [ 96240-10-7 ]
YieldReaction ConditionsOperation in experiment
95.1% With hydrazine hydrate; potassium hydroxide In water; toluene at 100 - 110℃; Dean-Stark; 9 Preparation of Amino-Triazolinone as Final Product Using Toluene/KOH 1.0 mole of the intermediate (hydrazine carboxylic acid) prepared in Example 6, 300 ml of toluene, 52.6 g (1.05 mole) of hydrazine hydrate, and 0.15 mole of KOH (40% aqueous solution) were added to a Dean-Stark reactor, and the obtained mixture was refluxed at a reaction temperature of 100° C. to 110° C. while removing water produced as a side product. ;After completion of the reaction, the resulting material was cooled to room temperature while adding water to the resulting material, which in turn was crystallized at 10° C. Then, the crystallized product was neutralized (pH=7-7.5) with sulfuric acid and filtered, followed by washing the obtained cake with water and drying, thereby preparing 135 g of a product (yield 95.1%, purity 99.48% (by GC), MP=171.48° C.).
  • 14
  • [ 1711-88-2 ]
  • [ 96240-10-7 ]
YieldReaction ConditionsOperation in experiment
With hydrazine hydrate; sodium hydroxide at 90 - 110℃; for 4h; 1.3 (3) Synthesis of 4-amino-3-isopropyl-5-oxo-11-1,2,4-triazole (triazolinone) The hydrazine hydrate and the second NaOH solution were added to the third reactor, stirred and heated to 90 ° C. The prepared oxadiazolone was added dropwise. After dropping, the reaction was carried out at 110 ° C for 4 hours, cooled to room temperature, Toluene solution, adjust the pH to neutral, freeze 2h, filter, filter cake, recrystallize, dry, get triazolinone, the second NaOH solution mass percentage concentration of 60%, oxadiazolone drop rate 1.5 mL / min, the mass ratio of hydrazine hydrate, second NaOH solution and oxadiazolone in step (3) is 3: 1: 8;
  • 15
  • C9H18N2O3 [ No CAS ]
  • [ 96240-10-7 ]
YieldReaction ConditionsOperation in experiment
85.3% With sodium carbonate; hydrazine hydrate at 95 - 100℃; for 3h; 1; 2; 3; 4; 5; 6; 7; 8 Example 3 44.5 g (0.50 mol) of isobutyric acid and 133.5 g of n-butanol were placed at room temperature.In a 500 mL reaction flask, start stirring and slowly add dropwise32.9g (0.525mol)80% hydrazine hydrate. After the dropwise addition is completed, the temperature is raised to reflux and dehydrated.When the 23 mL of water is removed, the heating is turned off.The water bath is cooled to 10~15 °C,Product 1 was obtained.Slowly pass 52.5g (0.525mol) phosgene at 1015°C,It took 2 hours and continued to incubate at this temperature for 3 hours to give product 2.Thereafter, 31.3 g (0.50 mol) of 80% hydrazine hydrate and 10.7 g (0.1 mol) of sodium carbonate were charged, and the mixture was heated to reflux at 95 to 100 ° C for 3 hours.The reaction is over. The layer was allowed to stand and the upper n-butanol was separated.The lower aqueous phase continues to cool down to 20 to 40 ° C.Adjust the pH to 6~7 with 30% hydrochloric acid, then continue to cool down to 0~5 °C, and continue stirring at this temperature for half an hour, suction filtration, a small amount of water washing,Drying gave product 3 (yield 85.3%, purity 99.5%).
  • 16
  • [ 497-18-7 ]
  • [ 97-87-0 ]
  • [ 96240-10-7 ]
YieldReaction ConditionsOperation in experiment
76.8% 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; 5 Put 100 mL of N,N-dimethylformamide into a 500 mL four-necked flask, start stirring, put 89.2 g (0.98 mol) carbohydrazide and 71.2 g (0.51 mol) potassium carbonate, and heat to reflux. 147.1g (1.01mol) of n-butyl isobutyrate was added dropwise at reflux temperature, and the addition was completed in about 2 hours. Incubate at 140-145°C for 3 hours. After the reaction is complete, the N,N-dimethylformamide is removed under negative pressure, and then 100mL of water is poured into it, cooled to 0°C for crystallization, filtered, and dried to obtain 109.1g of white solid, the target product, with a purity of 98.1% , The yield is 76.8%.
  • 17
  • [ 497-18-7 ]
  • [ 97-62-1 ]
  • [ 96240-10-7 ]
YieldReaction ConditionsOperation in experiment
75.2% Stage #1: carbonodihydrazide With potassium carbonate In ethanol Reflux; Stage #2: Ethyl isobutyrate In ethanol at 70 - 75℃; for 4h; 1 Put 100mL ethanol into a 500mL four-neck flask, Turn on the stirring, put in 86.4g (0.95mol) carbohydrazide and 79.6g (0.57mol) potassium carbonate, and heat to reflux. Under reflux conditions, 115.0g (0.98mol) ethyl isobutyrate was added dropwise, and the addition was completed in about 1 hour. Incubate at 7075 for 3 hours, After the reaction is complete, 80ml of ethanol is removed, then 100ml of water is added to the reaction solution, the temperature is slowly reduced to 0°C for crystallization, and filtered After drying, 103.6 g of the target product was obtained as a white solid with a purity of 98.0%. The yield was 75.2%.
  • 18
  • [ 547-63-7 ]
  • [ 497-18-7 ]
  • [ 96240-10-7 ]
YieldReaction ConditionsOperation in experiment
73.1% Stage #1: carbonodihydrazide With lithium hydroxide In toluene Reflux; Stage #2: Methyl isobutyrate In toluene at 105 - 110℃; for 4h; 2 Put 100 mL of toluene into a 500 mL four-necked flask, start stirring, put 86.4 g (0.95 mol) carbohydrazide and 26.4 g (1.09 mol) lithium hydroxide, and heat to reflux. 102.1g (0.99mol) methyl isobutyrate was added dropwise at reflux temperature, and the addition was completed in about 2 hours. Incubate at 105-110°C for 2 hours. After the reaction is complete, the toluene is removed under negative pressure, and then 100 mL of water is poured in, cooled to 0°C for crystallization, filtered, and dried to obtain 100.7 g of white solid, which is the target product, with a purity of 98.0% and a yield of 73.1%.
  • 19
  • [ 497-18-7 ]
  • [ 79-31-2 ]
  • [ 96240-10-7 ]
YieldReaction ConditionsOperation in experiment
74.8% 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; 3; 4 Put 100mL water into a 500mL four-neck flask, turn on the stirring, put 84.6g (0.93mol) carbohydrazide and 86.3g (0.97mol) isobutyric acid, Raise the temperature to 6065, and keep it for 5 hours at this temperature, Then 40.0g (0.99mol) sodium hydroxide was put into the reaction solution, Continue to heat up to reflux and keep it for about 3 hours under reflux conditions, After the reaction is completed, slowly lower the temperature to 0°C to crystallize, filter, After drying, 100.6 g of the target product was obtained as a white solid with a purity of 98.3%. The yield was 74.8%.
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