JPH06329658A - Chromene derivative and its production - Google Patents
Chromene derivative and its productionInfo
- Publication number
- JPH06329658A JPH06329658A JP5141204A JP14120493A JPH06329658A JP H06329658 A JPH06329658 A JP H06329658A JP 5141204 A JP5141204 A JP 5141204A JP 14120493 A JP14120493 A JP 14120493A JP H06329658 A JPH06329658 A JP H06329658A
- Authority
- JP
- Japan
- Prior art keywords
- organic solvent
- solvent
- formula
- compound
- chromene
- 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
- 150000008371 chromenes Chemical class 0.000 title abstract description 4
- 238000004519 manufacturing process Methods 0.000 title description 3
- 239000003960 organic solvent Substances 0.000 claims abstract description 11
- 150000001875 compounds Chemical class 0.000 claims abstract description 10
- GGSUCNLOZRCGPQ-UHFFFAOYSA-N diethylaniline Chemical compound CCN(CC)C1=CC=CC=C1 GGSUCNLOZRCGPQ-UHFFFAOYSA-N 0.000 claims abstract description 10
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 6
- 239000002904 solvent Substances 0.000 claims abstract description 6
- 239000003849 aromatic solvent Substances 0.000 claims abstract description 5
- 238000006462 rearrangement reaction Methods 0.000 claims abstract description 4
- 239000002202 Polyethylene glycol Substances 0.000 claims abstract description 3
- 229920001223 polyethylene glycol Polymers 0.000 claims abstract description 3
- 238000000034 method Methods 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
- 239000011968 lewis acid catalyst Substances 0.000 claims description 2
- 230000000749 insecticidal effect Effects 0.000 abstract description 5
- LCNICRUMHQOPIP-UHFFFAOYSA-N 8-tert-butyl-5-methyl-2h-chromene Chemical compound O1CC=CC2=C1C(C(C)(C)C)=CC=C2C LCNICRUMHQOPIP-UHFFFAOYSA-N 0.000 abstract description 3
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 abstract description 3
- 229910052801 chlorine Inorganic materials 0.000 abstract description 3
- 239000000460 chlorine Substances 0.000 abstract description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract description 2
- 229910052736 halogen Inorganic materials 0.000 abstract 2
- 150000002367 halogens Chemical class 0.000 abstract 2
- GOYDNIKZWGIXJT-UHFFFAOYSA-N 1,2-difluorobenzene Chemical compound FC1=CC=CC=C1F GOYDNIKZWGIXJT-UHFFFAOYSA-N 0.000 abstract 1
- KAHOASGBQWCOPB-UHFFFAOYSA-N 1-tert-butyl-4-methyl-2-prop-2-ynoxybenzene Chemical compound CC1=CC=C(C(C)(C)C)C(OCC#C)=C1 KAHOASGBQWCOPB-UHFFFAOYSA-N 0.000 abstract 1
- 239000004215 Carbon black (E152) Substances 0.000 abstract 1
- 239000002841 Lewis acid Substances 0.000 abstract 1
- 229930195733 hydrocarbon Natural products 0.000 abstract 1
- 150000002430 hydrocarbons Chemical class 0.000 abstract 1
- 150000007517 lewis acids Chemical class 0.000 abstract 1
- -1 chromene compound Chemical class 0.000 description 8
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000003905 agrochemical Substances 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 150000002429 hydrazines Chemical class 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 1
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
- ANMHZLQLLYTBLA-UHFFFAOYSA-N 1-tert-butyl-2-[1-[1-(2-tert-butyl-5-methylphenyl)prop-2-ynoxy]prop-2-ynyl]-4-methylbenzene Chemical compound C(C)(C)(C)C1=C(C=C(C=C1)C)C(C#C)OC(C#C)C1=C(C=CC(=C1)C)C(C)(C)C ANMHZLQLLYTBLA-UHFFFAOYSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 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
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical group [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- RCTYPNKXASFOBE-UHFFFAOYSA-M chloromercury Chemical compound [Hg]Cl RCTYPNKXASFOBE-UHFFFAOYSA-M 0.000 description 1
- QZHPTGXQGDFGEN-UHFFFAOYSA-N chromene Chemical compound C1=CC=C2C=C[CH]OC2=C1 QZHPTGXQGDFGEN-UHFFFAOYSA-N 0.000 description 1
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 1
- 229940117389 dichlorobenzene Drugs 0.000 description 1
- 230000008034 disappearance Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 150000002730 mercury Chemical class 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- KZJPVUDYAMEDRM-UHFFFAOYSA-M silver;2,2,2-trifluoroacetate Chemical compound [Ag+].[O-]C(=O)C(F)(F)F KZJPVUDYAMEDRM-UHFFFAOYSA-M 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- GGCZERPQGJTIQP-UHFFFAOYSA-N sodium;9,10-dioxoanthracene-2-sulfonic acid Chemical compound [Na+].C1=CC=C2C(=O)C3=CC(S(=O)(=O)O)=CC=C3C(=O)C2=C1 GGCZERPQGJTIQP-UHFFFAOYSA-N 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000006276 transfer reaction Methods 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
Classifications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts
Landscapes
- Pyrane Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Description
【０００１】[0001]
【産業上の利用分野】本発明は新規クロメン誘導体およ
びその製法に関する。該クロメン化合物は生理活性物
質、特に農薬の中間体として有用である。FIELD OF THE INVENTION The present invention relates to a novel chromene derivative and a process for producing the same. The chromene compound is useful as an intermediate for physiologically active substances, especially agricultural chemicals.
【０００２】[0002]
【従来の技術】クロメンへのアリールプロパルギルエー
テルの熱転位反応についてはＪ．Ｏｒｇ．Ｃｈｅｍ．３
７ Ｐ８４１（１９７２）において、また金属触媒を用
いる転移反応についてはＨｅｌｖ．Ｃｈｅｍ．Ａｃｔａ
５６ ２９８１（１９７３）および特開平２−８５２
７５号においてすでに公知であるが、本発明のクロメン
誘導体は新規化合物であり、そのものの製法およびそれ
が農薬の中間体として有用であることは知られていな
い。The thermal rearrangement reaction of aryl propargyl ether to chromene is described in J. Org. Chem. Three
7 P841 (1972) and for transfer reactions using metal catalysts, see Helv. Chem. Acta
56 2981 (1973) and JP-A-2-852.
As already known in No. 75, the chromene derivative of the present invention is a novel compound, and its production method and its usefulness as an intermediate for agricultural chemicals are not known.
【０００３】[0003]
【発明が解決しようとする課題】本発明者は、農薬のう
ち高い殺虫活性を有するヒドラジン系誘導体を探索すべ
く、その原料となる中間体の合成を試みた。DISCLOSURE OF THE INVENTION The inventors of the present invention have attempted to synthesize an intermediate as a raw material for a hydrazine derivative having high insecticidal activity among agricultural chemicals.
【０００４】[0004]
【課題を解決するための手段】その結果、特定のクロメ
ン化合物が高い殺虫活性を有するヒドラジン系誘導体の
中間体として極めて優れたものであることを見い出し
た。すなわち本発明は式As a result, they have found that a specific chromene compound is extremely excellent as an intermediate of a hydrazine derivative having a high insecticidal activity. That is, the present invention is a formula
【０００５】[0005]
【化４】 [Chemical 4]
【０００６】（式中Ｒ1 はＣ1 〜Ｃ2 のアルキル基また
はハロゲン原子を、Ｒ2 はＣ4 〜Ｃ6の第３級アルキル
基またはハロゲン原子を、Ｒ3 、Ｒ4 およびＲ5 は水素
原子またはメチル基を示す）で示されるクロメン誘導体
およびその製法に関する。以下本発明を詳細に説明す
る。式（１）の化合物は以下のようにして製造すること
ができる。すなわち式(Wherein R 1 is a C 1 -C 2 alkyl group or a halogen atom, R 2 is a C 4 -C 6 tertiary alkyl group or a halogen atom, and R 3 , R 4 and R 5 are A hydrogen atom or a methyl group) and a process for producing the same. The present invention will be described in detail below. The compound of formula (1) can be produced as follows. Ie the formula
【０００７】[0007]
【化５】 [Chemical 5]
【０００８】（式中Ｒ1 、Ｒ2 、Ｒ3 、Ｒ4 およびＲ5
は前記と同じものを意味する）で示される化合物を
（１）有機溶媒の存在下もしくは非存在下、高温にて、
または（２）有機溶媒およびルイス酸触媒の存在下転位
反応を行うことによって製造することができる。上記反
応で用いる有機溶媒としては、例えば（１）の場合、ジ
エチレングリコール、トリエチレングリコールなどのポ
リエチレングリコール系溶媒またはＮ，Ｎ−ジメチルア
ニリン、Ｎ，Ｎ−ジエチルアニリン、ｏ−ジクロロベン
ゼンなどの芳香族系溶媒が挙げられ、好ましくはＮ，Ｎ
−ジエチルアニリンである。また（２）の場合、トルエ
ン、ジクロロベンゼンなどの芳香族系溶媒または、クロ
ロホルム、１，１，１−トリクロロエタンなどの塩素系
炭化水素溶媒が挙げられ、好ましくはｏ−ジクロロベン
ゼンである。(Wherein R 1 , R 2 , R 3 , R 4 and R 5
Means the same as above), (1) in the presence or absence of an organic solvent, at high temperature,
Alternatively, (2) it can be produced by carrying out a rearrangement reaction in the presence of an organic solvent and a Lewis acid catalyst. As the organic solvent used in the above reaction, for example, in the case of (1), a polyethylene glycol solvent such as diethylene glycol or triethylene glycol, or an aromatic solvent such as N, N-dimethylaniline, N, N-diethylaniline or o-dichlorobenzene. System solvents, preferably N, N
-Diethylaniline. In the case of (2), an aromatic solvent such as toluene or dichlorobenzene or a chlorinated hydrocarbon solvent such as chloroform or 1,1,1-trichloroethane may be mentioned, and o-dichlorobenzene is preferable.
【０００９】反応温度は（１）の場合、通常１５０〜２
５０℃であり、好ましくは２００〜２２０℃である。
（２）の場合は通常室温〜２００℃であり、好ましくは
１５０〜１８０℃である。触媒としては通常、銀トリフ
ルオロアセテートなどの銀塩、塩化水銀などの水銀塩、
塩化銅などの銅塩、塩化亜鉛などの亜鉛塩であり、通常
０．１〜１０ｍｏｌ％、好ましくは０．５〜５ｍｏｌ％
使用する。本発明の方法で得られる式（１）におけるＲ
1 としては例えばメチル、エチル、塩素、臭素またはヨ
ウ素原子が挙げられ、Ｒ2 としては例えばｔｅｒｔ−ブ
チル、１，１，２−トリメチルプロピルまたは１，１−
ジメチルプロピル基、塩素、臭素またはヨウ素原子など
が挙げられる。本発明の式（１）で示される化合物の例
としては、８−ｔ−ブチル−５−メチル−２Ｈ−クロメ
ンが挙げられ、この化合物は次いで式When the reaction temperature is (1), it is usually 150 to 2
It is 50 ° C., preferably 200 to 220 ° C.
In the case of (2), it is usually room temperature to 200 ° C, preferably 150 to 180 ° C. The catalyst is usually a silver salt such as silver trifluoroacetate, a mercury salt such as mercury chloride,
It is a copper salt such as copper chloride or a zinc salt such as zinc chloride, and is usually 0.1 to 10 mol%, preferably 0.5 to 5 mol%.
use. R in the formula (1) obtained by the method of the present invention
Examples of 1 include methyl, ethyl, chlorine, bromine or iodine atoms, and examples of R 2 include tert-butyl, 1,1,2-trimethylpropyl or 1,1-
Examples thereof include a dimethylpropyl group, chlorine, bromine or iodine atom. Examples of the compound represented by the formula (1) of the present invention include 8-t-butyl-5-methyl-2H-chromene.
【００１０】[0010]
【化６】 [Chemical 6]
【００１１】で示される化合物に変換され、式（３）の
化合物は高い殺虫活性を有するヒドラジン系化合物の製
造に用いることができる。The compound of formula (3), which is converted into the compound of formula (3), can be used for the production of a hydrazine compound having a high insecticidal activity.
【００１２】[0012]
【発明の効果】本発明により、高い殺虫活性を有するヒ
ドラジン誘導体の原料とする中間体が高純度で製造でき
るようになった。INDUSTRIAL APPLICABILITY According to the present invention, an intermediate used as a raw material for a hydrazine derivative having a high insecticidal activity can be produced with high purity.
【００１３】[0013]
【実施例】以下に実施例により本発明を説明する。 実施例１ ８−ｔ−ブチル−５−メチル−２Ｈ−クロメンの製造：
２−ｔ−ブチル−５−メチルフェニルプロパルギルエー
テル（３６７ｇ，１．８２ｍｏｌ）をＮ，Ｎ−ジエチル
アニリン９００ｍｌに溶解し、２２０℃の油浴にて２時
間加熱撹拌した。ＧＣにて原料ピークの消失を確認した
のち、反応液を冷却し、酢酸エチル１．５ｌ加え分液ロ
ートに移し、１０％塩酸水溶液（１ｌ×２）にてＮ，Ｎ
−ジエチルアニリンを有機層から除去した。さらに有機
層を水およびブラインで中性になるまで十分洗浄後、芒
硝乾燥した。ろ過および溶媒留去を経て目的物（３６３
ｇ，ＧＣ純度９３．７％）を褐色オイルとして得た。1 Ｈ−ＮＭＲ（９０ＭＨｚ，ＣＤＣｌ3 ） δ（ｐｐｍ）：１．３５（ｓ，９Ｈ） ２．２５（ｓ，３Ｈ） ４．６５（ｄｄ，２Ｈ，Ｊ＝１．６Ｈｚ，４．０Ｈｚ） ５．８６（ｄｔ，１Ｈ，Ｊ＝４．０Ｈｚ，９．９Ｈｚ） ６．６２（ｄｔ，１Ｈ，Ｊ＝１．６Ｈｚ，９．９Ｈｚ） ６．６７（ｄ，１Ｈ，Ｊ＝８．２Ｈｚ） ７．０３（ｄ，１Ｈ，Ｊ＝８．２Ｈｚ）EXAMPLES The present invention will be described below with reference to examples. Example 1 Preparation of 8-t-butyl-5-methyl-2H-chromene:
2-t-Butyl-5-methylphenylpropargyl ether (367 g, 1.82 mol) was dissolved in 900 ml of N, N-diethylaniline, and the mixture was heated with stirring in an oil bath at 220 ° C for 2 hours. After confirming the disappearance of the raw material peaks by GC, the reaction solution was cooled, ethyl acetate (1.5 l) was added, and the mixture was transferred to a separating funnel.
-Diethylaniline was removed from the organic layer. Further, the organic layer was sufficiently washed with water and brine until it became neutral, and dried with sodium sulfate. The desired product (363
g, GC purity 93.7%) was obtained as a brown oil. 1 H-NMR (90 MHz, CDCl 3 ) δ (ppm): 1.35 (s, 9H) 2.25 (s, 3H) 4.65 (dd, 2H, J = 1.6 Hz, 4.0 Hz) 5 .86 (dt, 1H, J = 4.0 Hz, 9.9 Hz) 6.62 (dt, 1H, J = 1.6 Hz, 9.9 Hz) 6.67 (d, 1H, J = 8.2 Hz) 7 0.03 (d, 1H, J = 8.2Hz)
Claims (6)
子を、Ｒ2 はＣ4 〜Ｃ6の第３級アルキル基またはハロ
ゲン原子を、Ｒ3 、Ｒ4 、Ｒ5 はそれぞれ独立して水素
原子またはメチル基を示す）で示されるクロメン誘導
体。1. The formula: (In the formula, R 1 is a C 1 -C 2 alkyl group or a halogen atom, R 2 is a C 4 -C 6 tertiary alkyl group or a halogen atom, and R 3 , R 4 , and R 5 are independent of each other. Represents a hydrogen atom or a methyl group).
基であり、Ｒ3 、Ｒ4 、Ｒ5 が水素原子である請求項１
に記載の化合物。2. R 1 is a methyl group, R 2 is a t-butyl group, and R 3 , R 4 , and R 5 are hydrogen atoms.
The compound according to.
記載のものを示す）で示される化合物を、（１）有機溶
媒の存在下もしくは非存在下高温にて、または（２）有
機溶媒およびルイス酸触媒の存在下転位反応を行うこと
を特徴とする式 【化３】 （式中Ｒ1 、Ｒ2 、Ｒ3 、Ｒ4 およびＲ5 は請求項１に
記載のものを示す）で示されるクロメン誘導体の製法。3. The formula: (Wherein R 1 , R 2 , R 3 , R 4 and R 5 are as defined in claim 1), the compound (1) at high temperature in the presence or absence of an organic solvent, Or (2) a formula characterized by carrying out a rearrangement reaction in the presence of an organic solvent and a Lewis acid catalyst. (Wherein R 1 , R 2 , R 3 , R 4 and R 5 are as defined in claim 1).
基であり、Ｒ3 、Ｒ4 およびＲ5 が水素原子である請求
項３に記載の方法。4. The method according to claim 3, wherein R 1 is a methyl group, R 2 is a t-butyl group, and R 3 , R 4 and R 5 are hydrogen atoms.
または芳香族系溶媒である請求項３または４記載の方
法。5. The method according to claim 3 or 4, wherein the organic solvent is a polyethylene glycol solvent or an aromatic solvent.
ある請求項５記載の方法。6. The method according to claim 5, wherein the organic solvent is N, N-diethylaniline.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP5141204A JPH06329658A (en) | 1993-05-21 | 1993-05-21 | Chromene derivative and its production |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP5141204A JPH06329658A (en) | 1993-05-21 | 1993-05-21 | Chromene derivative and its production |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH06329658A true JPH06329658A (en) | 1994-11-29 |
Family
ID=15286569
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP5141204A Pending JPH06329658A (en) | 1993-05-21 | 1993-05-21 | Chromene derivative and its production |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH06329658A (en) |
-
1993
- 1993-05-21 JP JP5141204A patent/JPH06329658A/en active Pending
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