JPS62277366A - Production of delta2-1,2,4-triazolin-5-one derivative - Google Patents
Production of delta2-1,2,4-triazolin-5-one derivativeInfo
- Publication number
- JPS62277366A JPS62277366A JP11990086A JP11990086A JPS62277366A JP S62277366 A JPS62277366 A JP S62277366A JP 11990086 A JP11990086 A JP 11990086A JP 11990086 A JP11990086 A JP 11990086A JP S62277366 A JPS62277366 A JP S62277366A
- Authority
- JP
- Japan
- Prior art keywords
- triazolin
- formula
- production
- structural formula
- compound represented
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 6
- 150000001875 compounds Chemical class 0.000 claims abstract description 12
- 238000006396 nitration reaction Methods 0.000 claims 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract description 10
- 230000000802 nitrating effect Effects 0.000 abstract description 8
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 abstract description 6
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 abstract description 6
- 229910017604 nitric acid Inorganic materials 0.000 abstract description 6
- 239000003795 chemical substances by application Substances 0.000 abstract description 5
- 239000002904 solvent Substances 0.000 abstract description 3
- 239000003905 agrochemical Substances 0.000 abstract description 2
- 239000000463 material Substances 0.000 abstract 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 238000000034 method Methods 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- -1 alkali metal salt Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 125000000717 hydrazino group Chemical group [H]N([*])N([H])[H] 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
Abstract
Description
【発明の詳細な説明】
本発明は構造式（Ｉ）：
Ｎｏ、 Ｃ）（３
で表わされるΔ”−１，２，４−トリアゾリン−５−オ
ンの製法に関するものである。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a process for producing Δ''-1,2,4-triazolin-5-one represented by the structural formula (I): No, C)(3).
本発明によって得られる構造式（１）で表わされる化合
物は、文献未記載の新規化合物であり、農薬、例えば特
開昭６０−２５５７８０号公報等に記載されている化合
物を製造するための有用な中間体である。本発明は構造
式ｍで表わされる化合物の製法を提供するものである。The compound represented by the structural formula (1) obtained by the present invention is a new compound that has not been described in any literature, and is useful for producing agricultural chemicals, such as the compounds described in JP-A No. 60-255780. It is an intermediate. The present invention provides a method for producing a compound represented by structural formula m.
本発明の製法を例えば図式的に示すと以下の如く表わさ
れる。For example, the manufacturing method of the present invention can be diagrammatically expressed as follows.
即ち、構造式（１）で表わされる化合物は構造式（ｎ）
で表わされる化合物を溶媒の存在下にニトロ化剤でニト
ロ化することにより製造することができる。That is, the compound represented by structural formula (1) has structural formula (n)
It can be produced by nitrating the compound represented by with a nitrating agent in the presence of a solvent.
本反応で使用できるニトロ化剤としては、一般的に芳香
族化合物の芳香環のニトロ化に使用するニトロ化剤であ
れば良く、例えば硝酸と硫酸の混合物、硝酸と無水酢酸
との混合物、又は硝酸のアルカリ金属塩と硫酸との混合
物などを挙げることができる。The nitrating agent that can be used in this reaction may be any nitrating agent that is generally used for nitrating the aromatic ring of an aromatic compound, such as a mixture of nitric acid and sulfuric acid, a mixture of nitric acid and acetic anhydride, or Examples include a mixture of an alkali metal salt of nitric acid and sulfuric acid.
溶媒としては、本反応を著しく阻害しないものであれば
良く、例えば硫酸、酢酸、シクロルエタン等を挙げるこ
とができる。ニトロ化剤は一般式（ＩＩ）で表わされる
化合物１モルに対して１．０乃至′２．０モルの範囲か
ら適宜選択すれば良い。Any solvent may be used as long as it does not significantly inhibit this reaction, and examples thereof include sulfuric acid, acetic acid, and cycloethane. The nitrating agent may be appropriately selected from the range of 1.0 to 2.0 mol per mol of the compound represented by the general formula (II).
反応温度は一１０℃から５０℃の範囲から選択すれば良
く、反応時間は（Ｒ５乃至１０時間の範囲から選択すれ
ば良い。The reaction temperature may be selected from the range of -10°C to 50°C, and the reaction time may be selected from the range of (R5 to 10 hours).
反応終了後、反応液を常法により処理することによシ目
的物を採取することができる。After the reaction is completed, the desired product can be collected by treating the reaction solution in a conventional manner.
本発明の構造式（ＩＩ）で表わされる化合物は以下に示
す方法により製造することができる。The compound represented by structural formula (II) of the present invention can be produced by the method shown below.
（式中、Ｂｔ及びＲ２は同一でも異っても良く低級アル
キル基を示し、Ａは酸素原子又は硫黄原子を示す。）
即ち、構造式（ＩＩ）で表わされる化合物は構造式（至
）で表わされるヒドラジノと一般式（財）で表わされる
化合物を塩基の存在下に反応させることにより製造する
ことができる。(In the formula, Bt and R2 may be the same or different and represent a lower alkyl group, and A represents an oxygen atom or a sulfur atom.) That is, the compound represented by the structural formula (II) is It can be produced by reacting the hydrazino represented by the compound represented by the general formula (I) in the presence of a base.
以下に本発明の実施例を示す。Examples of the present invention are shown below.
実施例＋ −（２−クロロ−５−二トロフェニル）−３
−メチル−Δ！−１，２，４−）リアゾリン−５−オン
の製造
＋ｎｓｓ＋（α０５モル）の１−（２−クロロフェニル
）−５−メチル−Δ”−１，２，４−トリアゾリン−５
−オンを３０ｍの濃硫酸に溶解し、０℃以下の温度で、
８ｄの６０チ硝酸及び２０−の濃硫酸の混合液を滴下し
た。滴下終了後、３０分反応させ、その後反応を夜を室
県に冷却し、氷水中に注ぎ、析出する結晶をＰ取、乾燥
し、目的物１２．１７を得た。Example + -(2-chloro-5-nitrophenyl)-3
-Methyl-Δ! -Production of 1,2,4-) riazolin-5-one + nss + (α05 mol) of 1-(2-chlorophenyl)-5-methyl-Δ”-1,2,4-triazoline-5
-on was dissolved in 30 m concentrated sulfuric acid, and at a temperature below 0°C,
A mixed solution of 8d of 60% nitric acid and 20% of concentrated sulfuric acid was added dropwise. After the completion of the dropwise addition, the reaction was allowed to proceed for 30 minutes, and then the reaction was cooled to room temperature overnight, poured into ice water, and the precipitated crystals were removed and dried to obtain the desired product 12.17.
Claims (1)
造式（ I ）： ▲数式、化学式、表等があります▼（ I ） で表わされるΔ＾２−トリアゾリン−５−オン誘導体の
製法。[Claims] Structural formula (II): ▲ Includes mathematical formulas, chemical formulas, tables, etc. ▼ Structural formula (I) characterized by nitration of the compound represented by (II): ▲ Numerical formulas, chemical formulas, tables, etc. ▼(I) A method for producing a Δ^2-triazolin-5-one derivative.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP11990086A JPS62277366A (en) | 1986-05-24 | 1986-05-24 | Production of delta2-1,2,4-triazolin-5-one derivative |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP11990086A JPS62277366A (en) | 1986-05-24 | 1986-05-24 | Production of delta2-1,2,4-triazolin-5-one derivative |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS62277366A true JPS62277366A (en) | 1987-12-02 |
Family
ID=14772999
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP11990086A Pending JPS62277366A (en) | 1986-05-24 | 1986-05-24 | Production of delta2-1,2,4-triazolin-5-one derivative |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS62277366A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5011933A (en) * | 1990-02-26 | 1991-04-30 | Fmc Corporation | Nitration of phenyl triazolinones |
-
1986
- 1986-05-24 JP JP11990086A patent/JPS62277366A/en active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5011933A (en) * | 1990-02-26 | 1991-04-30 | Fmc Corporation | Nitration of phenyl triazolinones |
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