JP2019123673A - Method of producing dichloroquinone derivative - Google Patents
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- 238000000034 method Methods 0.000 title claims abstract description 18
- JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 claims abstract description 42
- 150000001875 compounds Chemical class 0.000 claims abstract description 30
- 238000004519 manufacturing process Methods 0.000 claims abstract description 25
- YRIZYWQGELRKNT-UHFFFAOYSA-N 1,3,5-trichloro-1,3,5-triazinane-2,4,6-trione Chemical compound ClN1C(=O)N(Cl)C(=O)N(Cl)C1=O YRIZYWQGELRKNT-UHFFFAOYSA-N 0.000 claims abstract description 19
- 229950009390 symclosene Drugs 0.000 claims abstract description 19
- 150000007524 organic acids Chemical class 0.000 claims abstract description 10
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 21
- 238000006243 chemical reaction Methods 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 235000011054 acetic acid Nutrition 0.000 description 6
- 239000007789 gas Substances 0.000 description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
- 229910052801 chlorine Inorganic materials 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 4
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 238000005660 chlorination reaction Methods 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 150000002367 halogens Chemical class 0.000 description 3
- 235000011044 succinic acid Nutrition 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- NRCMAYZCPIVABH-UHFFFAOYSA-N Quinacridone Chemical compound N1C2=CC=CC=C2C(=O)C2=C1C=C1C(=O)C3=CC=CC=C3NC1=C2 NRCMAYZCPIVABH-UHFFFAOYSA-N 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000004040 coloring Methods 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 239000001384 succinic acid Substances 0.000 description 2
- 0 *C(C(C(C(*)=C(C(O)=O)C1=O)=O)=C1Cl)=O Chemical compound *C(C(C(C(*)=C(C(O)=O)C1=O)=O)=C1Cl)=O 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 239000003125 aqueous solvent Substances 0.000 description 1
- 239000003899 bactericide agent Substances 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000012320 chlorinating reagent Substances 0.000 description 1
- 235000015165 citric acid Nutrition 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 150000003444 succinic acids Chemical class 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
Abstract
Description
本発明は、ジクロロキノン誘導体の製造方法に関する。 The present invention relates to a method for producing dichloroquinone derivatives.
下記一般式（２）で表される化合物（スクシニロコハク酸類）は、赤〜紫色の有用な色材であるキナクリドン類の出発原料として非常に重要である。一方、スクシニロコハク酸類の酸化体である、下記一般式（１）で表されるジクロロキノン誘導体（ジハロキノン類）は、スクシニロコハク酸類に塩素ガスや臭素ガス等のハロゲンガスを作用させて製造されることが知られている。しかし、スクシニロコハク酸類にハロゲンガスを反応させる方法は、不純物が生じやすいとともに、その取り扱いに特別の配慮が必要なハロゲンガスを使用する方法であることから、さほど注目されている製造方法であるとは言えない。 The compound (succinillo succinic acid) represented by the following general formula (2) is very important as a starting material of quinacridone which is a useful coloring material of red to purple. On the other hand, a dichloroquinone derivative (dihaloquinones) represented by the following general formula (1), which is an oxidized form of succinyrosuccinic acid, is produced by reacting succinyrosuccinic acid with a halogen gas such as chlorine gas or bromine gas. Are known. However, the method of reacting halogenous gases with succinyrosuccinic acid is a method that uses halogen gas that requires special consideration for its handling as well as impurities that are likely to be generated, so it may be said that it is a production method that has received much attention I can not say.
近年、ハロゲンガスを使用しない簡便な方法として、４モル当量のＮ−クロロスクシンイミドをスクシニロコハク酸類に作用させてジハロキノン類を合成する方法が報告されている（非特許文献１）。 In recent years, as a simple method that does not use a halogen gas, a method of synthesizing dihaloquinones by causing 4 molar equivalents of N-chlorosuccinimide to act on succiniro succinic acids has been reported (Non-patent Document 1).
しかしながら、非特許文献１で報告された方法は、基質であるスクシニロコハク酸類に対して、比較的高価なＮ−クロロスクシンイミドを相当過剰に反応させることが必要な方法である。このため、工業的に有利であるとは言えず、汎用性の高い製造方法ではなかった。 However, the method reported in Non-Patent Document 1 is a method that requires a relatively expensive reaction of relatively expensive N-chlorosuccinimide with a substrate succiniro succinic acid. For this reason, it can not be said that it is industrially advantageous, and it was not a highly versatile manufacturing method.
また、一般式（１）で表されるジハロキノン類をキナクリドン類の製造中間体として用いると、塩素分子が脱離基として作用し、塩化水素の脱離に伴って反応が進行する。すなわち、非特許文献１で報告された方法を採用すると、最終生成物であるキナクリドン類の製造コストは、過剰に用いるＮ−クロロスクシンイミドのコストに依存することになる。このため、非特許文献１で報告された方法は、やはり工業的に有利な方法であるとは言えなかった。 Further, when the dihaloquinones represented by the general formula (1) are used as an intermediate for producing quinacridones, chlorine molecules act as a leaving group, and the reaction proceeds with the elimination of hydrogen chloride. That is, when the method reported in Non-patent Document 1 is adopted, the production cost of the final product quinacridone depends on the cost of N-chlorosuccinimide used in excess. For this reason, the method reported in Non-Patent Document 1 can not be said to be an industrially advantageous method either.
本発明は、このような従来技術の有する問題点に鑑みてなされたものであり、その課題とするところは、汎用性が高く、工業的プロセスに容易に適用可能であるとともに、製造コスト面でも有利なジクロロキノン誘導体の製造方法を提供することにある。 The present invention has been made in view of the problems of the prior art, and the problems to be solved by the present invention are high in versatility and easily applicable to industrial processes, and also in terms of manufacturing cost. It is an object of the present invention to provide a process for the preparation of advantageous dichloroquinone derivatives.
すなわち、本発明によれば、以下に示すジクロロキノン誘導体の製造方法が提供される。
［１］下記一般式（１）で表されるジクロロキノン誘導体の製造方法であって、
下記一般式（２）で表される化合物に対し、１．０〜１．２モル当量のＮ−クロロスクシンイミドを有機酸中で反応させた後、引き続き、１．０〜１．２モル当量のトリクロロイソシアヌル酸を反応させる工程を有するジクロロキノン誘導体の製造方法。
That is, according to the present invention, a method for producing a dichloroquinone derivative shown below is provided.
[1] A method for producing a dichloroquinone derivative represented by the following general formula (1),
After reacting 1.0 to 1.2 molar equivalents of N-chlorosuccinimide in the organic acid with respect to the compound represented by the following general formula (2), subsequently, 1.0 to 1.2 molar equivalents of A process for producing a dichloroquinone derivative, comprising the step of reacting trichloroisocyanuric acid.
［２］前記有機酸が酢酸である前記［１］に記載のジクロロキノン誘導体の製造方法。 [2] The method for producing a dichloroquinone derivative according to [1], wherein the organic acid is acetic acid.
本発明によれば、汎用性が高く、工業的プロセスに容易に適用可能であるとともに、製造コスト面でも有利なジクロロキノン誘導体の製造方法を提供することができる。 According to the present invention, it is possible to provide a method for producing a dichloroquinone derivative which is highly versatile and easily applicable to an industrial process and advantageous in terms of production cost.
＜ジクロロキノン誘導体の製造方法＞
以下、本発明の実施の形態について説明するが、本発明は以下の実施の形態に限定されるものではない。本発明のジクロロキノン誘導体の製造方法（以下、単に「本発明の製造方法」とも記す）は、下記一般式（１）で表されるジクロロキノン誘導体の製造方法である。そして、本発明の製造方法は、下記一般式（２）で表される化合物に対し、１．０〜１．２モル当量のＮ−クロロスクシンイミドを有機酸中で反応させた後、引き続き、１．０〜１．２モル当量のトリクロロイソシアヌル酸を反応させる工程（反応工程）を有する。以下、本発明の製造方法の詳細について説明する。
<Method for producing dichloroquinone derivative>
Hereinafter, although the embodiment of the present invention is described, the present invention is not limited to the following embodiment. The method for producing a dichloroquinone derivative of the present invention (hereinafter, also simply referred to as “production method of the present invention”) is a method for producing a dichloroquinone derivative represented by the following general formula (1). Then, according to the production method of the present invention, after 1.0 to 1.2 molar equivalents of N-chlorosuccinimide are reacted in the organic acid with respect to the compound represented by the following general formula (2), 1 It has a process (reaction process) of reacting .0 to 1.2 molar equivalents of trichloroisocyanuric acid. Hereinafter, the details of the production method of the present invention will be described.
トリクロロイソシアヌル酸は、例えば、プール等の殺菌剤として用いられることが知られている。また、安価であるとともに安定性に優れており、工業的に扱いやすい試薬である。そして、トリクロロイソシアヌル酸は、有効塩素率がより高い試薬である。例えば、Ｎ−クロロスクシンイミドの有効塩素率が５１％であるのに対し、トリクロロイソシアヌル酸の有効塩素率は９１％である（Ｏｒｇａｎｉｃ Ｐｒｏｃｅｓｓ Ｒｅｓｅａｒｃｈ ａｎｄ Ｄｅｖｅｌｏｐｍｅｎｔ，２００２，６，ｐ．３８４−３９３）。 Trichloroisocyanuric acid is known to be used, for example, as a bactericidal agent such as a pool. In addition, it is an inexpensive reagent that is excellent in stability and industrially easy to handle. And trichloroisocyanuric acid is a reagent with a higher effective chlorine rate. For example, the effective chlorine rate of trichloroisocyanuric acid is 91% while the effective chlorine rate of N-chlorosuccinimide is 51% (Organic Process Research and Development, 2002, 6, p. 384-393).
本発明の製造方法では、一般式（２）で表される化合物を塩素化するための試薬（塩素化剤）として、Ｎ−クロロスクシンイミドとともにトリクロロイソシアヌル酸を用いる。Ｎ−クロロスクシンイミドだけでなく、トリクロロイソシアヌル酸を用いることで、高い製造収率を維持しつつ、高価であるとともに工業的にも不利なＮ−クロロスクシンイミドの使用量を低減することができる。 In the production method of the present invention, trichloroisocyanuric acid is used together with N-chlorosuccinimide as a reagent (chlorinating agent) for chlorinating a compound represented by the general formula (2). By using trichloroisocyanuric acid as well as N-chlorosuccinimide, the amount of expensive and industrially disadvantageous N-chlorosuccinimide can be reduced while maintaining a high production yield.
反応工程では、まず、一般式（２）で表される化合物に対し、Ｎ−クロロスクシンイミドを有機酸中で反応させる。一般式（２）で表される化合物の具体例としては、下記式（２ａ）〜（２ｄ）で表される化合物を挙げることができる。 In the reaction step, first, N-chlorosuccinimide is reacted in an organic acid with respect to the compound represented by the general formula (2). As a specific example of a compound represented by General formula (2), the compound represented by following formula (2a)-(2d) can be mentioned.
Ｎ−クロロスクシンイミドの量は、一般式（２）で表される化合物に対して、１．０〜１．２モル当量である。一般式（２）で表される化合物に対するＮ−クロロスクシンイミドの量が１．０モル当量未満であると、塩素化が不十分になる。一方、１．２モル当量超とするとコスト面で不利になる。 The amount of N-chlorosuccinimide is 1.0 to 1.2 molar equivalents relative to the compound represented by the general formula (2). If the amount of N-chlorosuccinimide is less than 1.0 molar equivalent to the compound represented by the general formula (2), chlorination will be insufficient. On the other hand, if it is more than 1.2 molar equivalents, it will be disadvantageous in cost.
一般式（２）で表される化合物にＮ−クロロスクシンイミドを反応させる際の温度及び時間は特に限定されず、適宜設定することができる。具体的には、６０〜１００℃の温度範囲で、３０分〜１０時間程度反応させればよい。 The temperature and the time at the time of making N-chlorosuccinimide react with the compound represented by General formula (2) are not specifically limited, It can set suitably. Specifically, the reaction may be performed for about 30 minutes to 10 hours in a temperature range of 60 to 100 ° C.
反応工程では、Ｎ−クロロスクシンイミドを反応させた後、好ましくは反応生成物等を単離することなく、引き続きトリクロロイソシアヌル酸を反応させる。より具体的には、Ｎ−クロロスクシンイミドを反応させた反応系にトリクロロイソシアヌル酸を添加し、反応させればよい。Ｎ−クロロスクシンイミドを反応させずに、トリクロロイソシアヌル酸のみを一般式（２）で表される化合物に反応させても塩素化することはできず、一般式（１）で表される化合物を得ることはできない。 In the reaction step, after reacting N-chlorosuccinimide, trichloroisocyanuric acid is subsequently reacted, preferably without isolating a reaction product or the like. More specifically, trichloroisocyanuric acid may be added to a reaction system in which N-chlorosuccinimide is reacted, and then reacted. Even if only trichloroisocyanuric acid is reacted with the compound represented by the general formula (2) without reacting N-chlorosuccinimide, chlorination can not be carried out, and the compound represented by the general formula (1) is obtained. It is not possible.
トリクロロイソシアヌル酸の量は、一般式（２）で表される化合物に対して、１．０〜１．２モル当量である。一般式（２）で表される化合物に対するトリクロロイソシアヌル酸の量が１．０モル当量未満であると、塩素化が不十分になる。一方、１．２モル当量超とするとコスト面で不利になる。 The amount of trichloroisocyanuric acid is 1.0 to 1.2 molar equivalents relative to the compound represented by the general formula (2). If the amount of trichloroisocyanuric acid relative to the compound represented by the general formula (2) is less than 1.0 molar equivalent, chlorination will be insufficient. On the other hand, if it is more than 1.2 molar equivalents, it will be disadvantageous in cost.
トリクロロイソシアヌル酸を反応させる際の温度及び時間は特に限定されず、適宜設定することができる。具体的には、６０〜１００℃の温度範囲で、１〜１０時間程度反応させればよい。 The temperature and time for reacting trichloroisocyanuric acid are not particularly limited, and can be set as appropriate. Specifically, the reaction may be performed for about 1 to 10 hours in a temperature range of 60 to 100 ° C.
一般式（２）で表される化合物と、Ｎ−クロロスクシンイミド及びトリクロロイソシアヌル酸とは、有機酸中で反応させる。有機酸を溶媒として用いることで、無機酸を用いる場合に比して、目的物である一般式（１）で表される化合物の分解を抑制し、収率を向上させることができる。なお、一般式（１）で表される化合物の分解を抑制して収率を向上させる観点からは、実質的に水が存在しない、非水溶媒中で反応させることが好ましい。有機酸としては、ギ酸、酢酸、クエン酸、シュウ酸、安息香酸などを挙げることができる。なかでも、水に溶けやすく、液体で扱いやすいことから酢酸が好ましい。トリクロロイソシアヌル酸を反応させた後は、必要に応じて精製等することで、目的とする一般式（１）で表される化合物を得ることができる。 The compound represented by the general formula (2) is reacted with N-chlorosuccinimide and trichloroisocyanuric acid in an organic acid. By using an organic acid as a solvent, the decomposition of the compound represented by the general formula (1), which is the target product, can be suppressed and the yield can be improved as compared with the case of using an inorganic acid. From the viewpoint of suppressing the decomposition of the compound represented by the general formula (1) to improve the yield, the reaction is preferably carried out in a non-aqueous solvent substantially free of water. As the organic acid, formic acid, acetic acid, citric acid, oxalic acid, benzoic acid and the like can be mentioned. Among them, acetic acid is preferable because it is easily soluble in water and easy to handle in liquid. After reacting trichloroisocyanuric acid, the compound represented by the general formula (1) can be obtained by purification and the like as required.
以下、本発明を実施例に基づいて具体的に説明するが、本発明はこれらの実施例に限定されるものではない。なお、実施例、比較例中の「部」及び「％」は、特に断らない限り質量基準である。製造した化合物の構造は、いずれも1Ｈ−ＮＭＲ及び質量分析により同定した。 EXAMPLES Hereinafter, the present invention will be specifically described based on examples, but the present invention is not limited to these examples. In the examples and comparative examples, "parts" and "%" are based on mass unless otherwise specified. The structures of the produced compounds were all identified by 1 H-NMR and mass spectrometry.
（実施例１）
式（２ａ）で表される化合物２５０部及びＮ−クロロスクシンイミド１５４部を酢酸２５００部に加え、８０℃で３０分加熱した。続けて、トリクロロイソシアヌル酸２６７部を加え、８０℃で２時間さらに加熱した。冷却後に水を加えて反応を停止した。ろ過及び水で洗浄後、８０℃で乾燥して、下記式（Ａ）で表される化合物（Ａ）２４７部（収率：７７％）を得た。
Example 1
250 parts of a compound represented by the formula (2a) and 154 parts of N-chlorosuccinimide were added to 2500 parts of acetic acid and heated at 80 ° C. for 30 minutes. Subsequently, 267 parts of trichloroisocyanuric acid were added and further heated at 80 ° C. for 2 hours. After cooling, water was added to stop the reaction. After filtration and washing with water, drying was carried out at 80 ° C. to obtain 247 parts (yield: 77%) of a compound (A) represented by the following formula (A).
（実施例２）
式（２ａ）で表される化合物２５０部に代えて、式（２ｂ）で表される化合物２８２部を使用したこと以外は、前述の実施例１と同様にして、下記式（Ｂ）で表される化合物（Ｂ）２７２部（収率：７７％）を得た。
(Example 2)
In the same manner as in Example 1 described above except that 282 parts of the compound represented by Formula (2b) is used instead of 250 parts of the compound represented by Formula (2a), a table of the following Formula (B) is used. 272 parts (yield: 77%) of the compound (B) were obtained.
（比較例１）
式（２ａ）で表される化合物２５０部及びＮ−クロロスクシンイミド６１７部を酢酸２５００部に加え、８０℃で２時間加熱した。冷却後に水を加えて反応を停止した。ろ過及び水で洗浄後、８０℃で乾燥して、化合物（Ａ）２４７部（収率：７７％）を得た。
(Comparative example 1)
250 parts of a compound represented by the formula (2a) and 617 parts of N-chlorosuccinimide were added to 2500 parts of acetic acid and heated at 80 ° C. for 2 hours. After cooling, water was added to stop the reaction. After filtration and washing with water, drying at 80 ° C. gave 247 parts (yield: 77%) of compound (A).
（比較例２）
式（２ａ）で表される化合物２５０部及びトリクロロイソシアヌル酸３５８部を酢酸２５００部に加え、８０℃で２時間加熱した。冷却後に水を加えて反応を停止した。ろ過及び水で洗浄したが、化合物（Ａ）の生成を確認することはできなかった。
(Comparative example 2)
250 parts of a compound represented by the formula (2a) and 358 parts of trichloroisocyanuric acid were added to 2500 parts of acetic acid and heated at 80 ° C. for 2 hours. After cooling, water was added to stop the reaction. Although filtration and washing with water, it was not possible to confirm the formation of compound (A).
実施例及び比較例の詳細を表１に示す。 Details of Examples and Comparative Examples are shown in Table 1.
本発明の製造方法は、色材として有用なキナクリドン類を製造するための原料や中間体として用いられるジクロロキノン誘導体を工業的に製造する方法として好適である。 The production method of the present invention is suitable as a method for industrially producing dichloroquinone derivatives used as raw materials and intermediates for producing quinacridones useful as coloring materials.
Claims (2)
下記一般式（２）で表される化合物に対し、１．０〜１．２モル当量のＮ−クロロスクシンイミドを有機酸中で反応させた後、引き続き、１．０〜１．２モル当量のトリクロロイソシアヌル酸を反応させる工程を有するジクロロキノン誘導体の製造方法。
After reacting 1.0 to 1.2 molar equivalents of N-chlorosuccinimide in the organic acid with respect to the compound represented by the following general formula (2), subsequently, 1.0 to 1.2 molar equivalents of A process for producing a dichloroquinone derivative, comprising the step of reacting trichloroisocyanuric acid.
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