JPH0285257A - Production of substituted pyrazole-4-carboxylic acid chloride - Google Patents
Production of substituted pyrazole-4-carboxylic acid chlorideInfo
- Publication number
- JPH0285257A JPH0285257A JP23855688A JP23855688A JPH0285257A JP H0285257 A JPH0285257 A JP H0285257A JP 23855688 A JP23855688 A JP 23855688A JP 23855688 A JP23855688 A JP 23855688A JP H0285257 A JPH0285257 A JP H0285257A
- Authority
- JP
- Japan
- Prior art keywords
- formula
- carboxylic acid
- blight
- acid chloride
- substituted pyrazole
- 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 17
- KWLGFSHSTADSKH-UHFFFAOYSA-N 1h-pyrazole-4-carbonyl chloride Chemical class ClC(=O)C=1C=NNC=1 KWLGFSHSTADSKH-UHFFFAOYSA-N 0.000 title claims description 8
- -1 alkyl hypochlorite Chemical compound 0.000 claims abstract description 6
- WQYVRQLZKVEZGA-UHFFFAOYSA-N hypochlorite Inorganic materials Cl[O-] WQYVRQLZKVEZGA-UHFFFAOYSA-N 0.000 claims abstract description 5
- LRGBDJBDJXZTTD-UHFFFAOYSA-N 1h-pyrazole-4-carbaldehyde Chemical class O=CC=1C=NNC=1 LRGBDJBDJXZTTD-UHFFFAOYSA-N 0.000 claims abstract description 3
- 125000000217 alkyl group Chemical group 0.000 claims abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 abstract description 9
- 239000002904 solvent Substances 0.000 abstract description 8
- 150000001875 compounds Chemical class 0.000 abstract description 5
- 238000009835 boiling Methods 0.000 abstract description 2
- 238000004821 distillation Methods 0.000 abstract description 2
- 239000000417 fungicide Substances 0.000 abstract description 2
- 238000001953 recrystallisation Methods 0.000 abstract description 2
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 abstract 2
- 235000016068 Berberis vulgaris Nutrition 0.000 abstract 1
- 241000335053 Beta vulgaris Species 0.000 abstract 1
- 241001451061 Choanephora cucurbitarum Species 0.000 abstract 1
- 240000007594 Oryza sativa Species 0.000 abstract 1
- 235000007164 Oryza sativa Nutrition 0.000 abstract 1
- 235000014443 Pyrus communis Nutrition 0.000 abstract 1
- 241000918585 Pythium aphanidermatum Species 0.000 abstract 1
- 241001361634 Rhizoctonia Species 0.000 abstract 1
- 241000228452 Venturia inaequalis Species 0.000 abstract 1
- 239000007795 chemical reaction product Substances 0.000 abstract 1
- 230000000694 effects Effects 0.000 abstract 1
- 230000000855 fungicidal effect Effects 0.000 abstract 1
- 235000009566 rice Nutrition 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 238000001816 cooling Methods 0.000 description 7
- 239000000203 mixture Substances 0.000 description 6
- IXZDIALLLMRYOU-UHFFFAOYSA-N tert-butyl hypochlorite Chemical compound CC(C)(C)OCl IXZDIALLLMRYOU-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 239000010779 crude oil Substances 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- XJEVHMGJSYVQBQ-UHFFFAOYSA-N 2,3-dihydro-1h-inden-1-amine Chemical compound C1=CC=C2C(N)CCC2=C1 XJEVHMGJSYVQBQ-UHFFFAOYSA-N 0.000 description 1
- GPWNWKWQOLEVEQ-UHFFFAOYSA-N 2,4-diaminopyrimidine-5-carbaldehyde Chemical compound NC1=NC=C(C=O)C(N)=N1 GPWNWKWQOLEVEQ-UHFFFAOYSA-N 0.000 description 1
- FQBOXJRHEZGATR-UHFFFAOYSA-N 3,5-dimethyl-1h-pyrazole-4-carbaldehyde Chemical compound CC1=NNC(C)=C1C=O FQBOXJRHEZGATR-UHFFFAOYSA-N 0.000 description 1
- 235000001674 Agaricus brunnescens Nutrition 0.000 description 1
- 239000004342 Benzoyl peroxide Substances 0.000 description 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- 238000007664 blowing Methods 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- ZKQFHRVKCYFVCN-UHFFFAOYSA-N ethoxyethane;hexane Chemical compound CCOCC.CCCCCC ZKQFHRVKCYFVCN-UHFFFAOYSA-N 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000012286 potassium permanganate Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 230000002747 voluntary effect Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Abstract
Description
【発明の詳細な説明】
〈産業上の利用分野〉
本発明は置換ピラゾール−４−カルボン酸クロリドの製
造法に関する。さらに詳しくは、特願昭６２−２８１５
６４号等の明細書に記載されている農園芸用殺菌剤を製
造する際の有用な中間体となり得る置換ピラゾール−４
−カルボン酸クロリドの製造法に関するものである。DETAILED DESCRIPTION OF THE INVENTION <Industrial Application Field> The present invention relates to a method for producing substituted pyrazole-4-carboxylic acid chlorides. For more details, please see the patent application No. 62-2815.
Substituted pyrazole-4 which can be a useful intermediate in producing agricultural and horticultural fungicides described in specifications such as No. 64
-This invention relates to a method for producing carboxylic acid chloride.
〈従来の技術〉
従来、置換ピラゾール−４−カルボン酸クロリドの製造
法としては、例えば次の方法が知らとを特徴とする一般
式
即ち、６−クロロ−１，８−ジメチルピラゾール−４−
カルボアルデヒドを過マンガン酸カリウムと反応させて
カルボン酸に導き、次いで過剰の塩化チオニルと反応さ
せることにより、５−クロロ−１，８−ジメチルピラゾ
ール−４−カルボン酸クロリドを得る方法（Ｊ 、 Ｌ
、 Ｈｕｐｐａ−ｔｚ；Ａｕ５ｔ、Ｊ、Ｃｈｅｍ、
、 ８６ 、１８５〜１４７ （１９８８）。〕。<Prior Art> Conventionally, as a method for producing substituted pyrazole-4-carboxylic acid chloride, for example, the following method is known.
A method for obtaining 5-chloro-1,8-dimethylpyrazole-4-carboxylic acid chloride by reacting carbaldehyde with potassium permanganate to lead to a carboxylic acid and then reacting with excess thionyl chloride (J, L
, Huppa-tz; Au5t, J. Chem.
, 86, 185-147 (1988). ].
〈発明が解決しようとする課題〉
しかしながら、上記の製造法では反応が多段階にわたり
、しかも反応操作も繁雑である等、工業的化実施する場
合、必ずしも充分なものとは３°い難い。<Problems to be Solved by the Invention> However, in the above production method, the reaction involves multiple stages and the reaction operation is complicated, so that it is not necessarily sufficient for industrial implementation.
〈課題を解決するための手段〉
本発明者らは、このような状況に鑑み、置換ピラゾール
−４−カルボン酸クロリドの製造法に関し、鋭意検討し
た結果、一般式
〔式中、Ｒ１はメチル基、エチル基またはトリで示され
る置換ピラゾール−４−カルボアルデヒドを一般式
％式％（２）
〔式中、Ｒ茸は炭素数１〜６の直鎖または分校とにより
、１段階で、容易にかつ高収率で一般ば
〔式中、Ｒ１は前記と同じ意味を表わす。〕で示される
置換ピラゾール−４−カルボン酸クロリドを有利に製造
できることを見い出し本発明に至った。<Means for Solving the Problems> In view of the above circumstances, the present inventors have made extensive studies regarding the method for producing substituted pyrazole-4-carboxylic acid chloride, and have found that the general formula [wherein R1 is a methyl group] , an ethyl group or a tri-substituted pyrazole-4-carbaldehyde with the general formula % formula % (2) [wherein R mushroom is a linear or branched chain having 1 to 6 carbon atoms, it can be easily prepared in one step. and generally in high yield [wherein R1 represents the same meaning as above]. It was discovered that the substituted pyrazole-4-carboxylic acid chloride represented by the following formula can be advantageously produced, leading to the present invention.
上記反応において、溶媒は必らずしも必要ではないが、
好ましくは溶媒の存在下に行なわれる。用いられる溶媒
としては、四塩化炭素、ジクロロエタン、クロロホルム
等のハロゲン化炭化水素類、トルエン等の炭化水素類、
酢酸エチル等のエステル類である。In the above reaction, a solvent is not necessarily required, but
It is preferably carried out in the presence of a solvent. Solvents used include halogenated hydrocarbons such as carbon tetrachloride, dichloroethane, and chloroform, hydrocarbons such as toluene,
These are esters such as ethyl acetate.
上記反応に用いられる試剤の量は、一般式〔ηで示され
る置換ピラゾール−４−カルボアルデヒド１当量に対し
て、一般式（２）で示される次亜塩素酸アルキルは、通
常１〜１０当量、好ましくは１〜２当量の範囲である。The amount of the reagent used in the above reaction is usually 1 to 10 equivalents of the alkyl hypochlorite represented by the general formula (2) per 1 equivalent of the substituted pyrazole-4-carbaldehyde represented by the general formula [η] , preferably in the range of 1 to 2 equivalents.
上記反応温度は、通常θ℃〜溶媒の沸点、好ましくは１
０℃〜５０℃の範囲である。上記反応に要する時間は通
常１０分〜２４時間であり、反応終了後は、反応液を減
圧下で濃縮することにより、所望の一般式（２）で示さ
れる置換ピラゾール−４−カルボン酸クロリドが得られ
、必要に応じて、蒸留、再結晶等の手段によりさらに精
製することもできる。The above reaction temperature is usually θ°C to the boiling point of the solvent, preferably 1
It is in the range of 0°C to 50°C. The time required for the above reaction is usually 10 minutes to 24 hours, and after the reaction is completed, the reaction solution is concentrated under reduced pressure to obtain the desired substituted pyrazole-4-carboxylic acid chloride represented by general formula (2). If necessary, it can be further purified by means such as distillation and recrystallization.
なお、上記反応に於いて試剤として用いる一般式（資）
で示される次亜塩素酸アルキルは［Ｃｈａｔｔ−ａｗａ
ｙ 、Ｆ 、Ｄ、 、 ａｎｄ Ｈａｃｋｅｂｅｒｇ、
０．Ｇ） Ｊ、Ｃｈｅｍ、 Ｓｏｃ、。In addition, the general formula (capital) used as a reagent in the above reaction
The alkyl hypochlorite represented by [Chatt-awa
y, F., D., and Hackeberg,
0. G) J, Chem, Soc.
１２８．２９９９（１９２８）、１ 等の方法により
容易にカルボン酸誘導体の中間体として有用なピラゾー
ル−４−カルボン酸クロリドの製法に関し、本発明方法
により目的物を有利に製造することができる。Regarding the method for producing pyrazole-4-carboxylic acid chloride, which is useful as an intermediate for carboxylic acid derivatives, the desired product can be advantageously produced by the method of the present invention.
〈実施例〉
次に製造例および参考例にて本発明をより詳しく説明す
るが、本発明は下記の製造例のみに限定されるものでは
ない。<Example> Next, the present invention will be explained in more detail with reference to production examples and reference examples, but the present invention is not limited only to the following production examples.
製造例１
５−クロロ−１，８−ジメチルピラゾール−４−カルボ
アルデヒド１．Ｏｆを１ｍｌのジクロロエタンに溶解さ
せ、水冷下、次亜塩素酸ｔ−ブチル０．６８ Ｆを加え
、８時間攪拌した。さらに、次亜塩素酸ｔ−ブチル０．
６８ ｆを加え、水冷下、４時間攪拌した。反応液を減
圧下で濃縮し、粗油状物を得た。その中には６−クロロ
−１，８−シメチルビラゾール−４−カルボン酸クロリ
ドが１．１８ ？含まれていた。Production Example 1 5-chloro-1,8-dimethylpyrazole-4-carbaldehyde 1. Of was dissolved in 1 ml of dichloroethane, 0.68 F of t-butyl hypochlorite was added under water cooling, and the mixture was stirred for 8 hours. Furthermore, t-butyl hypochlorite 0.
68 f was added thereto, and the mixture was stirred for 4 hours under water cooling. The reaction solution was concentrated under reduced pressure to obtain a crude oil. Among them, 6-chloro-1,8-dimethylvirazole-4-carboxylic acid chloride is 1.18? It was included.
純収率 ９３％
ｌＨ−ＮＭＲ（ＣＤＣＪ、）
δｐｐｍ ２．４０（１３Ｈ，Ｓ）３．８０（８Ｈ，Ｓ
）製造例２〜５
製造例１と同様の反応を反応溶媒としてジクロロエタン
の代わりに以下の溶媒を用いて行なった。Pure yield 93% lH-NMR (CDCJ, ) δppm 2.40 (13H,S) 3.80 (8H,S
) Production Examples 2 to 5 The same reaction as in Production Example 1 was carried out using the following solvents instead of dichloroethane as the reaction solvent.
上記製造例１と同様にして製造することかで製造例６
５−クロロ−１−メチル−８−トリフルオロメチルピラ
ゾール−４−カルボン酸クロリド純収率 ９８％
ｔ Ｈ−ＮＭＲ（ＣＤＣａｓ ）
δｐｐｍ ８．９５（８Ｈ，Ｓ）
ｔ９Ｆ−ＮＭＲ（ＣＤＣｚｍ／ｃＦ、ＣへＨ）５ｍ）１
）ｍ ＋１５（８Ｆ、Ｓ）
製造例７
５−クロロ−８−エチル−１−メチルピラゾール−４−
カルボン酸クロリド
純収率 ９８％
Ｉ Ｈ−ＮＭＲ（ＣＤＣＪ、 ）
δｐｐｍ １．２５（８Ｈ，ｔ 、 Ｊ＝７．ＯＨｚ
）２．８５ （２Ｈ，Ｑ 、 Ｊ＝７．ＯＨ２）８．８
５（８Ｈ，Ｓ）
参考例１ （特願昭６２−２８１５６４号に記載の化合
物の製造）１．１．８−）ジメチル−２−オキサ−４−
アミノインダン１．１２およびピリジン０．５４ ｆを
ジクロロエタン１２ｍｊｌこ溶解させ、水冷下、５−ク
ロロ−１，８−ジメチルピラゾール−４−カルボン酸ク
ロリド１．２０ｆをジクロロエタン６ｍｌに溶解させた
溶液を滴下した。滴下後、室温で一晩攪拌し、次いで水
およびクロロホルムを加えて抽出した。有機層は１９６
塩酸、水で洗浄した後、乾燥、濃縮した。得られた粗結
晶をエーテル−ヘキサン溶媒にて洗浄し、乾燥すること
により、Ｎ−（１，１，８−トリメチル−２−、ｔキサ
−４−インダニル）−６−クロロ−１，８−ジメチルピ
ラゾール−４−カルボン酸アミド１．８５Ｆを得た。Production Example 6 5-chloro-1-methyl-8-trifluoromethylpyrazole-4-carboxylic acid chloride Pure yield 98% t H-NMR (CDCas) δppm 8 .95 (8H, S) t9F-NMR (CDCzm/cF, H to C) 5m) 1
) m +15 (8F, S) Production Example 7 5-chloro-8-ethyl-1-methylpyrazole-4-
Carboxylic acid chloride pure yield 98% IH-NMR (CDCJ, ) δppm 1.25 (8H,t, J=7.OHz
)2.85 (2H,Q, J=7.OH2)8.8
5(8H,S) Reference Example 1 (Production of the compound described in Japanese Patent Application No. 62-281564) 1.1.8-)dimethyl-2-oxa-4-
1.12 f of aminoindan and 0.54 f of pyridine were dissolved in 12 mjl of dichloroethane, and a solution of 1.20 f of 5-chloro-1,8-dimethylpyrazole-4-carboxylic acid chloride dissolved in 6 ml of dichloroethane was added dropwise under water cooling. did. After the dropwise addition, the mixture was stirred at room temperature overnight, and then extracted with water and chloroform. The organic layer is 196
After washing with hydrochloric acid and water, it was dried and concentrated. The obtained crude crystals were washed with an ether-hexane solvent and dried to give N-(1,1,8-trimethyl-2-,txa-4-indanyl)-6-chloro-1,8- Dimethylpyrazole-4-carboxylic acid amide 1.85F was obtained.
本発明の方法を他の試剤または基質を用いて実施した場
合について、参考例２〜４に示す。Reference Examples 2 to 4 show cases in which the method of the present invention was carried out using other reagents or substrates.
参考例２
５−クロロ−１，８−ジメチルピラゾール−４−カルボ
アルデヒド８．０２を１０ｍＪのジクロロエタンに溶解
させ、過酸化ベンゾイル０．４１２を加え、塩素ガスを
吹き込みながら、４時間加熱還流した。Reference Example 2 8.02 of 5-chloro-1,8-dimethylpyrazole-4-carbaldehyde was dissolved in 10 mJ of dichloroethane, 0.412 of benzoyl peroxide was added, and the mixture was heated under reflux for 4 hours while blowing chlorine gas.
反応液を減圧下で濃縮し、粗油状物を得た。The reaction solution was concentrated under reduced pressure to obtain a crude oil.
その中には、５−クロロ−１，８−ジメチルピラゾール
−４−カルボン酸クロリドが０．４８ Ｆ含まれていた
。It contained 0.48 F of 5-chloro-1,8-dimethylpyrazole-4-carboxylic acid chloride.
純収率 １８９６
参考例８
１．８．５−）ジメチルピラゾール−４−カルボアルデ
ヒド１．０２を１ｍＪのジクロロエタンに溶解させ、水
冷下、次亜塩素酸ｔ−ブチル０．７８ｆを加え、２時間
攪拌した。さらに、次亜塩素酸ｔ−ブチル０．７８ Ｆ
を加え、水冷下、５時間攪拌した。反応液を減圧下で濃
縮し、粗油状物を得た。その中には、１，８．５−トリ
メチルピラゾール−４−カルボン酸クロリドが０、８２
９含まれていた。Pure yield 1896 Reference example 8 1.8.5-) 1.02 of dimethylpyrazole-4-carbaldehyde was dissolved in 1 mJ of dichloroethane, 0.78 f of t-butyl hypochlorite was added under water cooling, and the mixture was stirred for 2 hours. Stirred. Furthermore, t-butyl hypochlorite 0.78 F
was added and stirred for 5 hours under water cooling. The reaction solution was concentrated under reduced pressure to obtain a crude oil. Among them, 1,8,5-trimethylpyrazole-4-carboxylic acid chloride is 0,82
9 included.
純収率 ２６％
参考例４
１．８−ジメチル−５−フルオロピラゾール−４−カル
ボアルデヒド１．０２をｔｍａのジクロロエタンに溶解
させ、水冷下、次亜塩素酸ｔ−ブチル０．７６ｆを加え
８時間攪拌した。さらに次亜塩素酸ｔ−ブチル０．７６
Ｆを加え、水冷下、４時間攪拌した。反応液を減圧下で
濃縮し、粗油状物を得た。その中には、１，８−ジメチ
ル−５−フルオロピラゾール−４−カルボン酸クロリド
が０．２４ ？含まれていた。Pure yield 26% Reference example 4 1.02 of 1.8-dimethyl-5-fluoropyrazole-4-carbaldehyde was dissolved in TMA dichloroethane, and 0.76 f of t-butyl hypochlorite was added under water cooling. Stir for hours. Furthermore, t-butyl hypochlorite 0.76
F was added, and the mixture was stirred for 4 hours under water cooling. The reaction solution was concentrated under reduced pressure to obtain a crude oil. Among them, 1,8-dimethyl-5-fluoropyrazole-4-carboxylic acid chloride is 0.24? It was included.
純収率 １９％ 手続補正書（自発） 昭和６３年１１月４日Net yield 19% Procedural amendment (voluntary) November 4, 1986
Claims (1)
ロメチル基を表わす。〕 で示される置換ピラゾール−４−カルボアルデヒトと一
般式 Ｒ＿２−ＯＣｌ 〔式中、Ｒ＿２は炭素数１〜５の直鎖または分枝状アル
キル基を表わす。〕 で示される次亜塩素酸アルキルとを反応させることを特
徴とする一般式 ▲数式、化学式、表等があります▼ 〔式中、Ｒ＿１は前記と同じ意味を表わす。〕で示され
る置換ピラゾール−４−カルボン酸クロリドの製造法。[Claims] General formula ▲ Numerical formula, chemical formula, table, etc. ▼ [In the formula, R_1 represents a methyl group, ethyl group, or trifluoromethyl group. ] Substituted pyrazole-4-carbaldehyde represented by the general formula R_2-OCl [In the formula, R_2 represents a straight chain or branched alkyl group having 1 to 5 carbon atoms. ] A general formula characterized by reacting with an alkyl hypochlorite represented by ▲ There are numerical formulas, chemical formulas, tables, etc. ▼ [In the formula, R_1 represents the same meaning as above. ] A method for producing substituted pyrazole-4-carboxylic acid chloride.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP23855688A JPH0285257A (en) | 1988-09-21 | 1988-09-21 | Production of substituted pyrazole-4-carboxylic acid chloride |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP23855688A JPH0285257A (en) | 1988-09-21 | 1988-09-21 | Production of substituted pyrazole-4-carboxylic acid chloride |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH0285257A true JPH0285257A (en) | 1990-03-26 |
Family
ID=17031998
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP23855688A Pending JPH0285257A (en) | 1988-09-21 | 1988-09-21 | Production of substituted pyrazole-4-carboxylic acid chloride |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0285257A (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0776889A1 (en) | 1995-12-01 | 1997-06-04 | Bayer Ag | Process for the production of 1,3-dimethyl-5-fluoro-pyrazol-4-carboxanilides |
| KR20000002788A (en) * | 1998-06-23 | 2000-01-15 | 성재갑 | Panesyl transferase inhibitor having pyrazole structure and manufacturing method of it |
| US6054473A (en) * | 1996-07-24 | 2000-04-25 | Bayer Aktiengesellschaft | 1,3-dimethyl-5-fluoro-pyrazole-4-carboxamide derivatives, their preparation and their use as microbicides |
| WO2008086962A2 (en) * | 2007-01-18 | 2008-07-24 | Bayer Cropscience Aktiengesellschaft | Method for producing substituted pyrazolecarboxylic acid chlorides |
| CN103140477A (en) * | 2010-04-23 | 2013-06-05 | 拜耳知识产权股份有限公司 | Process for preparing 5-fluoro-1-alkyl-3-fluoroalkyl-1h-pyrazole-4-carbonyl chlorides and fluorides |
-
1988
- 1988-09-21 JP JP23855688A patent/JPH0285257A/en active Pending
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0776889A1 (en) | 1995-12-01 | 1997-06-04 | Bayer Ag | Process for the production of 1,3-dimethyl-5-fluoro-pyrazol-4-carboxanilides |
| US6054473A (en) * | 1996-07-24 | 2000-04-25 | Bayer Aktiengesellschaft | 1,3-dimethyl-5-fluoro-pyrazole-4-carboxamide derivatives, their preparation and their use as microbicides |
| KR20000002788A (en) * | 1998-06-23 | 2000-01-15 | 성재갑 | Panesyl transferase inhibitor having pyrazole structure and manufacturing method of it |
| WO2008086962A2 (en) * | 2007-01-18 | 2008-07-24 | Bayer Cropscience Aktiengesellschaft | Method for producing substituted pyrazolecarboxylic acid chlorides |
| WO2008086962A3 (en) * | 2007-01-18 | 2009-06-11 | Bayer Cropscience Ag | Method for producing substituted pyrazolecarboxylic acid chlorides |
| JP2010516641A (en) * | 2007-01-18 | 2010-05-20 | バイエル・クロツプサイエンス・アクチエンゲゼルシヤフト | Process for the preparation of substituted pyrazole carboxylic acid chlorides |
| US7977494B2 (en) | 2007-01-18 | 2011-07-12 | Bayer Cropscience Ag | Method for producing substituted pyrazolecarboxylic acid chlorides |
| KR101466130B1 (en) * | 2007-01-18 | 2014-11-27 | 바이엘 크롭사이언스 아게 | Method for producing substituted pyrazolecarboxylic acid chlorides |
| CN103140477A (en) * | 2010-04-23 | 2013-06-05 | 拜耳知识产权股份有限公司 | Process for preparing 5-fluoro-1-alkyl-3-fluoroalkyl-1h-pyrazole-4-carbonyl chlorides and fluorides |
| JP2013525324A (en) * | 2010-04-23 | 2013-06-20 | バイエル・インテレクチユアル・プロパテイー・ゲー・エム・ベー・ハー | Process for the preparation of 5-fluoro-1-alkyl-3-fluoroalkyl-1H-pyrazole-4-carbonyl chloride and fluoride |
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