JP4971170B2 - ピラゾールの調製のための方法 - Google Patents
ピラゾールの調製のための方法 Download PDFInfo
- Publication number
- JP4971170B2 JP4971170B2 JP2007537197A JP2007537197A JP4971170B2 JP 4971170 B2 JP4971170 B2 JP 4971170B2 JP 2007537197 A JP2007537197 A JP 2007537197A JP 2007537197 A JP2007537197 A JP 2007537197A JP 4971170 B2 JP4971170 B2 JP 4971170B2
- Authority
- JP
- Japan
- Prior art keywords
- formula
- compound
- methyl
- difluoromethyl
- preparation
- 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.)
- Expired - Fee Related
Links
- 0 Cc1n[n](*)cc1C(O*)=O Chemical compound Cc1n[n](*)cc1C(O*)=O 0.000 description 2
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three 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, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Description
式II
式III
R1がジフルオロメチル又はトリフルオロメチルであり;
R2がメチル又はエチルであり、そして/又は
R3がメチルである、
化合物の調製のために適当である。
5.7gの3−ジフルオロメチル−1H−ピラゾール−4−カルボン酸エチルエステル(30mmol)及び25mlのリン酸トリメチル(214mmol)の混合物を180℃の温度で18時間撹拌する。その後250mlの氷水混合物を添加する。生じた反応生成物を濾過し、水で洗浄し、そして50mlの酢酸エチル中に溶かす。有機相を50mlの塩化ナトリウム飽和溶液で洗浄し、そして硫酸ナトリウムで乾燥させ、そして蒸発により濃縮する。3.9g(64%の理論値)の3−ジフルオロメチル−1−メチル−1H−ピラゾール−4−カルボン酸エチルエステルが結晶形態において得られる(融点59−60℃)。
4.16gの3−トリフルオロメチル−1H−ピラゾール−4−カルボン酸エチルエステル(20mmol)及び10mlのリン酸トリメチル(86.4mmol)の混合物を180℃の温度で16時間撹拌する。その後200mlの氷水混合物を添加する。生じた反応生成物を濾過し、水で洗浄し、そして50mlの酢酸エチル中に溶かす。有機相をそれぞれ50mlの塩化ナトリウム飽和溶液で2回洗浄し、そして硫酸ナトリウムで乾燥させ、そして蒸発により濃縮する。4.0g(90%の理論値)の3−トリフルオロメチル−1−メチル−1H−ピラゾール−4−カルボン酸エチルエステルが結晶形態において得られる(融点55−57℃)。
2.08gの3−トリフルオロメチル−1H−ピラゾール−4−カルボン酸エチルエステル(10mmol)及び2.3mlのリン酸トリメチル(20mmol)の混合物を180℃の温度で16時間撹拌する。その後200mlの氷水混合物を添加する。生じた反応生成物を濾過し、水で洗浄し、そして50mlの酢酸エチル中に溶かす。有機相をそれぞれ50mlの塩化ナトリウム飽和溶液で2回洗浄し、そして硫酸ナトリウムで乾燥させ、そして蒸発により濃縮する。1.9g(86%の理論値)の3−トリフルオロメチル−1−メチル−1H−ピラゾール−4−カルボン酸エチルエステルが結晶形態において得られる(融点55−57℃)。
Claims (10)
- 前記反応が、溶媒の添加なしに行われる、請求項1に記載の方法。
- 前記式中、R 1 がジフルオロメチルである、請求項1に記載の方法。
- 前記式中、R 1 がジフルオロメチルである、請求項3に記載の使用。
- 前記式中、R 1 がジフルオロメチルである、請求項4に記載の方法。
- 前記式中、R 1 がジフルオロメチルであり;R 2 がエチルであり;そしてR 3 がメチルである、請求項1に記載の方法。
- 前記式中、R 1 がジフルオロメチルであり;R 2 がエチルであり;そしてR 3 がメチルである、請求項3に記載の使用。
- 前記式中、R 1 がジフルオロメチルであり;R 2 がエチルであり;そしてR 3 がメチルである、請求項4に記載の方法。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH17502004 | 2004-10-21 | ||
CH1750/04 | 2004-10-21 | ||
PCT/EP2005/011232 WO2006045504A1 (en) | 2004-10-21 | 2005-10-19 | Process for the preparation of pyrazoles |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2008517019A JP2008517019A (ja) | 2008-05-22 |
JP4971170B2 true JP4971170B2 (ja) | 2012-07-11 |
Family
ID=35784889
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2007537197A Expired - Fee Related JP4971170B2 (ja) | 2004-10-21 | 2005-10-19 | ピラゾールの調製のための方法 |
Country Status (17)
Country | Link |
---|---|
US (1) | US7678924B2 (ja) |
EP (1) | EP1805145B1 (ja) |
JP (1) | JP4971170B2 (ja) |
KR (1) | KR20070067163A (ja) |
CN (1) | CN101044119B (ja) |
AR (1) | AR051936A1 (ja) |
AU (1) | AU2005298922B2 (ja) |
BR (1) | BRPI0516994B1 (ja) |
CA (1) | CA2582141C (ja) |
EA (1) | EA010851B1 (ja) |
ES (1) | ES2399280T3 (ja) |
IL (1) | IL182421A (ja) |
MX (1) | MX2007004638A (ja) |
TW (1) | TWI357898B (ja) |
UA (1) | UA93860C2 (ja) |
WO (1) | WO2006045504A1 (ja) |
ZA (1) | ZA200702516B (ja) |
Families Citing this family (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE102006039909A1 (de) * | 2006-08-25 | 2008-03-13 | Bayer Cropscience Ag | Verfahren zum Herstellen von 3-Dihalomethyl-pyrazol-4-carbonsäurederivaten |
EP2133341A1 (de) * | 2008-02-25 | 2009-12-16 | Bayer CropScience AG | Verfahren zur regioselektiven Synthese von 1-Alkyl-3-haloalkyl-pyrazol-4-carbonsäure-Derivaten |
CN102471278B (zh) * | 2009-07-28 | 2015-04-01 | 先正达参股股份有限公司 | 关于吡唑的烷基化方法 |
ES2525489T3 (es) * | 2009-07-31 | 2014-12-23 | Syngenta Participations Ag | Procedimientos para la alquilación de pirazoles |
US9359304B2 (en) * | 2010-08-10 | 2016-06-07 | Syngenta Participations Ag | Process for the preparation of 3-haloalkylpyrazoles |
US8871947B2 (en) | 2013-02-04 | 2014-10-28 | KingChem LLC | Preparation of alkyl 3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid ester |
CN104379551B (zh) | 2013-12-09 | 2017-03-08 | 金凯有限责任公司 | 3‑二氟甲基‑1‑甲基‑1h‑吡唑‑4‑羧酸烷基酯及其类似物的制备方法 |
Family Cites Families (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP3374922B2 (ja) * | 1991-05-09 | 2003-02-10 | 日産化学工業株式会社 | 複素環式第3級アミンの製造方法 |
FR2682379B1 (fr) * | 1991-10-09 | 1994-02-11 | Rhone Poulenc Agrochimie | Nouveaux phenylpyrazoles fongicides. |
GB9405229D0 (en) * | 1994-03-17 | 1994-04-27 | Rhone Poulenc Agriculture | Compositions of matter |
JP2000044541A (ja) * | 1998-08-03 | 2000-02-15 | Mitsui Chemicals Inc | 1,3−ジアルキルピラゾール−4−カルボン酸エステルの製造法 |
JP4076806B2 (ja) * | 2002-07-15 | 2008-04-16 | 株式会社電業社機械製作所 | ジェットファン |
-
2005
- 2005-10-19 CN CN2005800360400A patent/CN101044119B/zh active Active
- 2005-10-19 TW TW094136471A patent/TWI357898B/zh not_active IP Right Cessation
- 2005-10-19 EA EA200700767A patent/EA010851B1/ru not_active IP Right Cessation
- 2005-10-19 BR BRPI0516994-1A patent/BRPI0516994B1/pt active IP Right Grant
- 2005-10-19 ES ES05795607T patent/ES2399280T3/es active Active
- 2005-10-19 AR ARP050104367A patent/AR051936A1/es not_active Application Discontinuation
- 2005-10-19 UA UAA200705360A patent/UA93860C2/ru unknown
- 2005-10-19 AU AU2005298922A patent/AU2005298922B2/en not_active Ceased
- 2005-10-19 JP JP2007537197A patent/JP4971170B2/ja not_active Expired - Fee Related
- 2005-10-19 EP EP05795607A patent/EP1805145B1/en active Active
- 2005-10-19 MX MX2007004638A patent/MX2007004638A/es active IP Right Grant
- 2005-10-19 WO PCT/EP2005/011232 patent/WO2006045504A1/en active Application Filing
- 2005-10-19 KR KR1020077009092A patent/KR20070067163A/ko active IP Right Grant
- 2005-10-19 US US11/577,511 patent/US7678924B2/en active Active
- 2005-10-19 CA CA2582141A patent/CA2582141C/en not_active Expired - Fee Related
-
2007
- 2007-03-27 ZA ZA200702516A patent/ZA200702516B/xx unknown
- 2007-04-10 IL IL182421A patent/IL182421A/en not_active IP Right Cessation
Also Published As
Publication number | Publication date |
---|---|
EA010851B1 (ru) | 2008-12-30 |
MX2007004638A (es) | 2007-06-08 |
BRPI0516994B1 (pt) | 2014-09-30 |
EA200700767A1 (ru) | 2007-10-26 |
CA2582141C (en) | 2013-06-11 |
TWI357898B (en) | 2012-02-11 |
TW200619201A (en) | 2006-06-16 |
EP1805145A1 (en) | 2007-07-11 |
US20090069572A1 (en) | 2009-03-12 |
AU2005298922A1 (en) | 2006-05-04 |
UA93860C2 (ru) | 2011-03-25 |
EP1805145B1 (en) | 2012-11-28 |
IL182421A0 (en) | 2007-07-24 |
US7678924B2 (en) | 2010-03-16 |
CN101044119B (zh) | 2012-03-14 |
BRPI0516994A (pt) | 2008-09-30 |
IL182421A (en) | 2012-12-31 |
WO2006045504A1 (en) | 2006-05-04 |
AU2005298922B2 (en) | 2012-01-19 |
ZA200702516B (en) | 2008-09-25 |
ES2399280T3 (es) | 2013-03-27 |
AR051936A1 (es) | 2007-02-21 |
JP2008517019A (ja) | 2008-05-22 |
KR20070067163A (ko) | 2007-06-27 |
CA2582141A1 (en) | 2006-05-04 |
CN101044119A (zh) | 2007-09-26 |
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