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Preparation method of 1-substituted-4-carbamoyl-1,2,4-triazol-5-one derivatives

A technology for carbamoyl and derivatives, which is applied in the field of preparation of 1-substituted-4-carbamoyl-1,2,4-triazol-5-one derivatives, and can solve problems such as complicated operation and high cost

Active Publication Date: 2011-11-23
HOKKO CHEM IND CO LTD (JP)
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Therefore, the operation is sometimes complicated and the cost is increased, and it cannot be said to be a preparation method that is advantageous for industrial production.

Method used

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  • Preparation method of 1-substituted-4-carbamoyl-1,2,4-triazol-5-one derivatives
  • Preparation method of 1-substituted-4-carbamoyl-1,2,4-triazol-5-one derivatives
  • Preparation method of 1-substituted-4-carbamoyl-1,2,4-triazol-5-one derivatives

Examples

Experimental program
Comparison scheme
Effect test

preparation example Construction

[0085]

[0086] In the present invention, as described above, in order to obtain the 1-substituted-4-carbamoyl-1,2,4-triazol-5-one derivative (I) as the target compound, step 2 is carried out after step 1, thereby First, the step 1 for obtaining the target 1-substituted-4-carbamoyl-1,2,4-triazol-5-one derivative (I) will be described.

[0087]

[0088] In step 1 of the present invention, in the selected from quaternary ammonium salt and In the presence of at least one phase transfer catalyst (B) of a salt, the 1-substituted-1,2,4-triazole-5- Ketone derivative and (b) alkali metal hydroxide (A) react, obtain the alkali metal salt ( During IIa), the by-produced water is removed by azeotropic distillation together with the solvent (C) and discharged to the outside of the system.

[0089] (Conditions of temperature and pressure and time)

[0090] The reaction in step 1 can be carried out at normal temperature (15-25° C.) or heating {the temperature depends on the type of s...

Synthetic example 1

[0140] Synthesis of 1-(2,4-dichlorophenyl)-1,2,4-triazol-5-one

[0141] Analysis of the reaction and purity was carried out by high-performance liquid chromatography (HPLC) under the following conditions.

[0142] Device: Shimadzu Corporation HPLC system, UV detector: SPD-10AVP, pump: LC-10ATVP, column oven: CTO-10ASVP, column: Japan GL Science (GL Science) Co., Ltd. Inertsil ODS-3 (column The particle size of filler: 5 μm, column inner diameter: 4.6mm, column length: 250mm), UV detection wavelength: 254nm, mobile layer solvent volume ratio and flow rate: acetonitrile: distilled water=60: 40, 1.0ml / min, (as the first 1 When analyzing the hydrazone of the intermediate product), methanol:distilled water=10:3, 0.5ml / min, (when analyzing the triazolinone and the target compound as the second intermediate product), use Japan Yamato (Yamato) The melting point of the compound was measured with a melting point analyzer MP-21 manufactured by Science Co., Ltd., and the mass spectrum w...

Synthetic example 2

[0148] Synthesis of N-isopropyl-N-2,4-difluorophenylcarbamoyl chloride

[0149] Analysis of reaction and purity was carried out by gas chromatography under the following conditions.

[0150] Device: Shimadzu Corporation GC-14B, column: G-100 (column length 20m, film thickness 0.5μm, ID 1.2mm), analysis conditions: 80°C (initial), 20°C / min (heating to 280°C (final)), detector: TCD (300° C.), carrier gas: helium (20 ml / min), and mass spectrometry of the compound was measured with a mass spectrometer SUN-200 manufactured by JEOL Ltd.

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Abstract

The invention provides a preparation method of 1-substituted-4-carbamoyl-1,2,4-triazol-5-one derivatives, which is low in cost and high in yield and purity and is represented as the following formula (I). The method is characterized in that in the presence of quaternary ammonium salt or salt, 1-substituted-1,2,4-triazol-5-one derivative reacts with an alkali metal hydroxide in aromatic hydrocarbon solvent and the byproduct water is simultaneously removed by azeotropic distillation. Then the obtained reaction mixture is added with amidogen formoxyl chloride for further reaction. In formula (I), x represents a halogen atom or a lower alkyl group, y represents a halogen atom, r represents lower alkyls, n and m independently represent an integer of 0 to 5.

Description

technical field [0001] The present invention relates to a preparation method of 1-substituted-4-carbamoyl-1,2,4-triazol-5-one derivatives. Background technique [0002] The following formula (I) [0003] [0004] The 1-substituted-4-carbamoyl-1,2,4-triazol-5-ketone derivative represented is a compound that can be used as an active ingredient of a herbicide, wherein, X represents a halogen atom or a lower alkyl group, and Y represents a halogen atom, R represents a lower alkyl group, and n and m represent an integer of 0-5. As its preparation method, known in an organic solvent, [0005] In the presence of dehydrochlorination agent, make the following formula (II) [0006] [0007] Represented 1-substituted-1,2,4-triazol-5-one derivatives with the following formula (III) [0008] [0009] The carbamoyl chloride reaction method represented, X, Y, R and n, m in the formula are as previously described (for example, refer to Patent Document 1); or make the two react ...

Claims

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Application Information

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IPC IPC(8): C07D249/12
Inventor 冲田洋行木户庸裕
Owner HOKKO CHEM IND CO LTD (JP)
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