JP2012504153A - ハロゲン化環式化合物の合成方法 - Google Patents
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- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
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- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/32—One oxygen, sulfur or nitrogen atom
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- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
Abstract
Description
ZおよびYは独立して、炭素またはヘテロ原子を表し、
Aは、環において0、1、2または3個の原子を含む、ZとYの間の結合基である)
の環式化合物を製造する方法であって、
(a)式R1−C(O)−X(X=フッ素、塩素または臭素であり、R1は上記で示される意味を有する)の酸ハロゲン化物を式(II)CH2=CH−OR2(II)(R2はアルキル基、アラルキル基またはアリール基である)のビニルエーテルに付加して、付加生成物を生成する工程と、(b)前記付加生成物を式(III)Y−A−Z(III)(Z、YおよびAは上記で定義されるとおりである)の化合物と反応させる工程と、を含む方法に関する。
のうちの1つに相当する、本発明の式(I)の化合物の製造に適切に用いられる。後者の場合、Aは適切には、−CH2−、−C(=O)−、−CH2−CH2およびCH2−C(=O)−および−C(=S)−から選択され、R3はHまたはC1〜C6アルキルである。
ZおよびYは独立して、炭素またはヘテロ原子を表し、
Aは、環において0、1、2または3個の原子を含む、ZとYの間の結合基である)の環式化合物を合成する方法であって、
式R1−C(O)−X(X=フッ素、塩素または臭素であり、R1は上記で示される意味を有する)の酸ハロゲン化物を式(II)CH2=CH−OR2(II)(R2は、アルキル基、アラルキル基またはアリール基である)のビニルエーテルに付加することによって得られる付加生成物を、ハロゲン化水素、特に塩化水素の存在下にて、式(III)Y−A−Z(III)(Z、YおよびAは上記で定義されるとおりである)の化合物と反応させる、方法にも関する。
6−(トリフルオロメチル)ピリミジン−2(1H)−オンの製造
トリフルオロアセチルクロリドをエチルビニルエーテルに付加することによって製造された、等モル量の4−エトキシ−1,1,1−トリフルオロ−3−ブテン−2−オン(ETFBO)を、機械攪拌機、還流冷却器および滴下漏斗を備えた三つ口フラスコにおけるメタノール2.2L中の尿素8.74モルの溶液に、N2雰囲気下にて約3時間にわたって、一滴ずつ添加した。反応混合物の温度を15℃未満に維持した。15分後、濃HCl溶液(32%)1.35Lを得られた冷却懸濁液に添加し、透明な溶液が得られた。その溶液をゆっくりと60℃に加熱し、2時間攪拌した後、懸濁液が形成した。60℃で一晩攪拌し、続いて0〜5℃で1時間攪拌した後、沈殿物を濾過除去した。pHが中性になるまで、残留物を水で洗浄し、続いてヘキサン(約500ml)で洗浄した。減圧下にて2Lフラスコ中で回転蒸発器にて一晩乾燥させた後、6−(トリフルオロメチル)ピリミジン−2(1H)−オンが無色の結晶として得られた。収量は1.2kgであった(理論収量85%)。
3−(トリフルオロメチル)1H−ピラゾールの製造
トリフルオロアセチルクロリドをエチルビニルエーテルに付加することによって製造された、等モル量のETFBOを、機械攪拌機、還流冷却器および滴下漏斗を備えた三つ口フラスコにおけるメタノール2.2L中のヒドラジン塩酸塩4.4モルの溶液に、N2雰囲気下にて約4時間にわたって、一滴ずつ添加した。反応混合物の温度を15℃未満に維持した。12時間還流した後、反応バッチを2Lフラスコにおいて濾過し、真空下で濃縮した(同一バッチが同一条件下で製造され、どちらの粗生成物の収率も約95%であった)。続いて、27ミリバールでショートパス真空蒸留によって、合わせた粗生成物を精製した。収量は1105gであり、理論収量92%に相当する。
CETFBOからの6−(トリフルオロメチル)ピリミジン−2(1H)−オンの製造
CETFBOの合成:約−30℃で約2時間冷却された三つ口フラスコ中で、トリフルオロアセチルクロリド4.0モルを濃縮した。−30℃で約2.5時間冷却された液体トリフルオロアセチルクロリドに、エチルビニルエーテル4.0モルを一滴ずつ添加した。HClを除去することなく、CETFBOが定量的に得られた。
3−ピリジンカルボン酸,1,2−ジヒドロ−2−オキソ−6−(トリフルオロメチル)−メチルエステル(MTFPMOC)の製造
約20分間にわたって激しく攪拌しながら、メチルマロンアミド(MMA)420ミリモルを氷冷トリエチルアミン(420ミリモル)に添加した。次いで、エチルビニルエーテルにTFACを付加することによって製造されたETFBOを、氷冷下にて約30分間にわたって一滴ずつ添加し、反応混合物の温度を10℃未満に維持した。次いで、反応混合物をさらに室温で20時間攪拌した。pHが3になるまで、その溶液に濃HCl溶液(2N)を添加した。溶液を酢酸エチルで抽出した後、有機相を水で洗浄し、硫酸ナトリウムで乾燥させた。回転蒸発器で揮発性化合物を除去した後、粗生成物が収率86%で得られた。メタノール/水から結晶化した後、MTFPMOCが純度>98%(GC)で得られた。
3−ピリジンカルボン酸,1,2−ジヒドロ−2−オキソ−6−(トリフルオロメチル)−エチルエステル(ETFPMOC)の製造
約20分間にわたって激しく攪拌しながら、エチルマロンアミド(EMA)420ミリモルを氷冷トリエチルアミン(420ミリモル)に添加した。次いで、エチルビニルエーテルにTFACを付加することによって製造されたETFBOを、氷冷下にて約30分間にわたって一滴ずつ添加し、反応混合物の温度を10℃未満に維持した。次いで、反応混合物をさらに室温で20時間攪拌した。pHが3になるまで、その溶液に濃HCl溶液(2N)を添加した。溶液を酢酸エチルで抽出した後、有機相を水で洗浄し、硫酸ナトリウムで乾燥させた。回転蒸発器で揮発性化合物を除去した後、粗生成物が収率86%で得られた。メタノール/水から結晶化した後、ETFPMOCが純度>98%(GC)で得られた。
Claims (17)
- 式(I):
ZおよびYは独立して、炭素またはヘテロ原子を表し
Aは、環において0、1、2または3個の原子を含む、ZとYの間の結合基である)
の環式化合物を製造する方法であって、
(a)式R1−C(O)−X(X=フッ素、塩素または臭素であり、R1は上記で示される意味を有する)の酸ハロゲン化物を式(II)CH2=CH−OR2(II)(R2はアルキル基、アラルキル基またはアリール基である)のビニルエーテルに付加して、付加生成物を生成する工程と、
(b)前記付加生成物を式(III)Y−A−Z(III)(Z、YおよびAは上記で定義されるとおりである)の化合物と反応させる工程と、
を含む方法。 - R1が、CF3、CF2HおよびCF2Clから好ましくは選択されるC1〜C3ハロゲン化アルキル基である、請求項1に記載の方法。
- R2が、C1〜C4アルキル基、好ましくはエチル基である、請求項1から6のいずれか一項に記載の方法。
- ZおよびYが独立して、酸素、硫黄、窒素および炭素から選択される、請求項1から7のいずれか一項に記載の方法。
- ZおよびYのうちの少なくとも1つが窒素である、請求項8に記載の方法。
- Aが、1または2個のカテナリー炭素原子を含む、請求項1から9のいずれか一項に記載の方法。
- 式(III)の前記化合物が、ヒドラジンまたはその含水化合物または塩酸塩、尿素、チオ尿素、マロン酸モノアミドおよびマロモノニトリルから選択される、請求項1から10のいずれか一項に記載の方法。
- 工程(a)で生成されたHXが、工程(b)に供給される、請求項1から12のいずれか一項に記載の方法。
- 工程(b)に供給された前記付加生成物が、工程(a)からの粗生成物である、請求項1から13のいずれか一項に記載の方法。
- 工程(b)の前記反応が、範囲−15℃〜+80℃の温度で行われる、請求項1から14のいずれか一項に記載の方法。
- 固液分離または蒸留によって、工程(b)の前記反応媒体から式(I)の前記化合物を単離することをさらに含む、請求項1から15のいずれか一項に記載の方法。
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US8431710B2 (en) | 2008-09-30 | 2013-04-30 | Solvay Sa | Process for the synthesis of halogenated cyclic compounds |
US8957254B2 (en) | 2009-07-06 | 2015-02-17 | Solvay Sa | Process for chemical synthesis from an alkenone made from a halogenated precursor |
BR112012000280B1 (pt) | 2009-07-06 | 2018-02-14 | Solvay Sa | "processo para preparar um precursor halogenado de uma alquenona, e, método para a fabricação de uma alquenona" |
EP2662359A1 (en) | 2012-05-08 | 2013-11-13 | Solvay Sa | Ionic Liquids, Method for manufacturing thereof, and Electrochemical Devices Comprising the Same |
JP6426090B2 (ja) | 2012-08-22 | 2018-11-21 | ソルヴェイ(ソシエテ アノニム) | アルケノンの製造方法 |
EP2936607B1 (en) * | 2012-12-20 | 2017-02-22 | Solvay SA | Salts of n-containing heterocyclic anions as components in electrolytes |
CN105324371A (zh) * | 2013-06-20 | 2016-02-10 | 巴斯夫欧洲公司 | 由吡啶基肼制备吡啶基吡唑化合物及其衍生物的方法 |
EP2987782A1 (en) | 2014-08-22 | 2016-02-24 | Solvay SA | Distillation process comprising at least two distillation steps to obtain purified halogenated carboxylic acid halide, and use of the purified halogenated carboxylic acid halide |
WO2016079122A1 (en) | 2014-11-17 | 2016-05-26 | Solvay Sa | A method for producing a chemical compound and apparatus therefor |
CN107001231A (zh) | 2014-11-17 | 2017-08-01 | 索尔维公司 | 包括至少两个蒸馏步骤以获得纯化的卤化的羧酸卤化物的蒸馏方法、以及该纯化的卤化的羧酸卤化物的用途 |
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KR20160131129A (ko) | 2016-11-15 |
US20110178297A1 (en) | 2011-07-21 |
JP6511346B2 (ja) | 2019-05-15 |
US8431710B2 (en) | 2013-04-30 |
CA2735921C (en) | 2017-03-21 |
US20130237710A1 (en) | 2013-09-12 |
JP6647268B2 (ja) | 2020-02-14 |
JP6180705B2 (ja) | 2017-08-16 |
EP2334645A1 (en) | 2011-06-22 |
KR20110066201A (ko) | 2011-06-16 |
EP2334645B1 (en) | 2019-11-06 |
CA2735921A1 (en) | 2010-04-08 |
CN106083710B (zh) | 2021-03-12 |
US8981115B2 (en) | 2015-03-17 |
CN102164898A (zh) | 2011-08-24 |
KR20190080972A (ko) | 2019-07-08 |
JP2015227339A (ja) | 2015-12-17 |
JP2020023533A (ja) | 2020-02-13 |
CN106083710A (zh) | 2016-11-09 |
JP2022028792A (ja) | 2022-02-16 |
WO2010037688A1 (en) | 2010-04-08 |
JP2018058869A (ja) | 2018-04-12 |
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