JP5077969B2 - 2−置換5−(1−アルキルチオ)アルキルピリジンの調製方法 - Google Patents
2−置換5−(1−アルキルチオ)アルキルピリジンの調製方法 Download PDFInfo
- Publication number
- JP5077969B2 JP5077969B2 JP2009549057A JP2009549057A JP5077969B2 JP 5077969 B2 JP5077969 B2 JP 5077969B2 JP 2009549057 A JP2009549057 A JP 2009549057A JP 2009549057 A JP2009549057 A JP 2009549057A JP 5077969 B2 JP5077969 B2 JP 5077969B2
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- JP
- Japan
- Prior art keywords
- alkyl
- substituted
- membered saturated
- saturated ring
- alkylthio
- 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.)
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/28—Radicals substituted by singly-bound oxygen or sulphur atoms
- C07D213/32—Sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/79—Acids; Esters
- C07D213/80—Acids; Esters in position 3
Description
R3はC1〜C4アルキルを表すか、あるいはR3はR1またはR2の一方と一緒になって4〜6員の飽和環を表し、
R4はC1〜C4アルキルまたはC1〜C4ハロアルキルを表す。)の調製方法であって、
a)置換エノン(II)
R5およびR6は、独立にC1〜C4アルキルを表す。)
をエナミン(III)
R7およびR8は、独立にC1〜C4アルキルを表すか、あるいはR7およびR8は、Nと一緒になって飽和または不飽和の5員環を表す。)
と縮合すること;
b)2,3,5−置換ピリジン(IV)
c)2−置換−5−(1−アルキルチオ)アルキルピリジン(I)を得るために、前記2,3,5−置換ピリジン(IV)を鹸化し、脱カルボキシル化すること;を含む方法に関する。この方法はR4がCF3を表す化合物を調製する場合に特に適している。
R3はC1〜C4アルキルを表すか、あるいはR3はR1またはR2の一方と一緒になって4〜6員の飽和環を表し、
R4はC1〜C4アルキルまたはC1〜C4ハロアルキルを表し、
R6はHまたはC1〜C4アルキルを表す。)に関する。
R3はC1〜C4アルキルを表すか、あるいはR3はR1またはR2の一方と一緒になって4〜6員の飽和環を表し、
R4はC1〜C4アルキルまたはC1〜C4ハロアルキルを表す。)の調製方法であって、
a)置換エノン(II)
R5およびR6は、独立にC1〜C4アルキルを表す)をエナミン(III)
R7およびR8は、独立にC1〜C4アルキルを表すか、あるいはR7およびR8は、Nと一緒になって飽和または不飽和の5員環を表す。)で縮合すること;
b)2,3,5−置換ピリジン(IV)
c)2−置換−5−(1−アルキルチオ)アルキルピリジン(I)を得るために前記2,3,5−置換ピリジン(IV)を鹸化し、脱カルボキシル化すること;を含む方法に関する。
実施例
Claims (5)
- 2−置換−5−(1−アルキルチオ)−アルキルピリジン(I)
R3はC1〜C4アルキルを表すか、あるいはR3はR1またはR2の一方と一緒になって4〜6員の飽和環を表し、
R4はC1〜C4アルキルまたはC1〜C4ハロアルキルを表す。)
の調製方法であって、
a)置換エノン(II)
R5およびR6は、独立にC1〜C4アルキルを表す。)
をエナミン(III)
R7およびR8は、独立にC1〜C4アルキルを表すか、あるいはR7およびR8は、Nと一緒になって飽和または不飽和の5員環を表す。)
と縮合すること;
b)2,3,5−置換ピリジン(IV)
を製造するために、アンモニアまたはアンモニアを生成できる試薬の存在下で、ステップa)からの反応混合物を環化すること;および
c)2−置換−5−(1−アルキルチオ)アルキルピリジン(I)を得るために、前記2,3,5−置換ピリジン(IV)を鹸化し、脱カルボキシル化すること;
を含む方法。 - R4がCF3を表す請求項1に記載の方法。
- R1がH原子を表し、R2がCH3を表し、R3がCH3を表す、請求項2に記載の方法。
- 式(IV)
R3はC1〜C4アルキルを表すか、あるいはR3はR1またはR2の一方と一緒になって4〜6員の飽和環を表し、
R4はC1〜C4アルキルまたはC1〜C4ハロアルキルを表し、
R6はHまたはC1〜C4アルキルを表す。)の化合物。 - R4がCF3を表す請求項4に記載の化合物。
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
PCT/US2007/003779 WO2008097234A1 (en) | 2007-02-09 | 2007-02-09 | Process for the preparation of 2-substituted-5-(1-alkylthio) alkylpyridines |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2010518077A JP2010518077A (ja) | 2010-05-27 |
JP5077969B2 true JP5077969B2 (ja) | 2012-11-21 |
Family
ID=38704937
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2009549057A Active JP5077969B2 (ja) | 2007-02-09 | 2007-02-09 | 2−置換5−(1−アルキルチオ)アルキルピリジンの調製方法 |
Country Status (14)
Country | Link |
---|---|
EP (1) | EP2114884B1 (ja) |
JP (1) | JP5077969B2 (ja) |
KR (1) | KR101364418B1 (ja) |
CN (1) | CN101611004B (ja) |
AT (1) | ATE491688T1 (ja) |
AU (1) | AU2007346135B2 (ja) |
BR (1) | BRPI0721386B8 (ja) |
CA (1) | CA2676072C (ja) |
DE (1) | DE602007011324D1 (ja) |
DK (1) | DK2114884T3 (ja) |
HK (1) | HK1139402A1 (ja) |
IL (1) | IL200000A (ja) |
MX (1) | MX2009008422A (ja) |
WO (1) | WO2008097234A1 (ja) |
Families Citing this family (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP2364971B1 (en) * | 2006-11-30 | 2014-04-30 | Dow AgroSciences LLC | 2,5-Disubstituted pyridines for the preparation of 2-substituted 5-(1-alkylthio)-alkylpyridines |
US7709648B2 (en) | 2007-02-09 | 2010-05-04 | Dow Agrosciences Llc | Process for the preparation of 2-substituted-5-(1-alkylthio)alkylpyridines |
EP2315750B1 (en) * | 2008-07-01 | 2012-11-07 | Dow AgroSciences LLC | Improved process for the preparation of 2-trifluoromethyl-5-(1-substituted)alkylpyridines |
DK2646424T3 (en) * | 2010-12-03 | 2016-01-11 | Dow Agrosciences Llc | PROCESSES FOR PREPARING Enamines |
EP2675797B1 (en) * | 2010-12-03 | 2016-03-16 | Dow AgroSciences LLC | Processes for the preparation of enamines |
PL2680696T3 (pl) * | 2010-12-03 | 2015-10-30 | Dow Agrosciences Llc | Sposób wytwarzania enamin |
Family Cites Families (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB2192877A (en) * | 1986-07-22 | 1988-01-27 | Shell Int Research | Herbicidal imidazolinyl compounds |
CN1942442B (zh) * | 2004-04-08 | 2012-10-31 | 美国陶氏益农公司 | 杀虫用n-取代亚磺酰亚胺 |
-
2007
- 2007-02-09 MX MX2009008422A patent/MX2009008422A/es active IP Right Grant
- 2007-02-09 WO PCT/US2007/003779 patent/WO2008097234A1/en active Application Filing
- 2007-02-09 BR BRPI0721386A patent/BRPI0721386B8/pt active IP Right Grant
- 2007-02-09 EP EP07750606A patent/EP2114884B1/en active Active
- 2007-02-09 DK DK07750606.1T patent/DK2114884T3/da active
- 2007-02-09 DE DE602007011324T patent/DE602007011324D1/de active Active
- 2007-02-09 CA CA2676072A patent/CA2676072C/en not_active Expired - Fee Related
- 2007-02-09 KR KR1020097016123A patent/KR101364418B1/ko active IP Right Grant
- 2007-02-09 CN CN2007800510939A patent/CN101611004B/zh active Active
- 2007-02-09 AU AU2007346135A patent/AU2007346135B2/en active Active
- 2007-02-09 AT AT07750606T patent/ATE491688T1/de active
- 2007-02-09 JP JP2009549057A patent/JP5077969B2/ja active Active
-
2009
- 2009-07-21 IL IL200000A patent/IL200000A/en not_active IP Right Cessation
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2010
- 2010-06-19 HK HK10106091.3A patent/HK1139402A1/xx not_active IP Right Cessation
Also Published As
Publication number | Publication date |
---|---|
DK2114884T3 (da) | 2011-03-28 |
AU2007346135B2 (en) | 2011-11-17 |
MX2009008422A (es) | 2009-08-18 |
CN101611004B (zh) | 2012-07-04 |
IL200000A (en) | 2013-06-27 |
DE602007011324D1 (de) | 2011-01-27 |
KR20100014364A (ko) | 2010-02-10 |
JP2010518077A (ja) | 2010-05-27 |
ATE491688T1 (de) | 2011-01-15 |
CA2676072C (en) | 2014-05-13 |
BRPI0721386B8 (pt) | 2022-06-28 |
HK1139402A1 (en) | 2010-09-17 |
KR101364418B1 (ko) | 2014-02-17 |
CA2676072A1 (en) | 2008-08-14 |
EP2114884B1 (en) | 2010-12-15 |
CN101611004A (zh) | 2009-12-23 |
BRPI0721386B1 (pt) | 2016-03-08 |
EP2114884A1 (en) | 2009-11-11 |
BRPI0721386A2 (pt) | 2012-12-25 |
IL200000A0 (en) | 2011-08-01 |
WO2008097234A1 (en) | 2008-08-14 |
AU2007346135A1 (en) | 2008-08-14 |
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