JP5320465B2 - α,β−不飽和カルボニルまたはスルホニル化合物にチオレート類を添加するための改善された方法 - Google Patents
α,β−不飽和カルボニルまたはスルホニル化合物にチオレート類を添加するための改善された方法 Download PDFInfo
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- JP5320465B2 JP5320465B2 JP2011523859A JP2011523859A JP5320465B2 JP 5320465 B2 JP5320465 B2 JP 5320465B2 JP 2011523859 A JP2011523859 A JP 2011523859A JP 2011523859 A JP2011523859 A JP 2011523859A JP 5320465 B2 JP5320465 B2 JP 5320465B2
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C319/00—Preparation of thiols, sulfides, hydropolysulfides or polysulfides
- C07C319/14—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of sulfides
- C07C319/18—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of sulfides by addition of thiols to unsaturated compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/22—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and doubly-bound oxygen atoms bound to the same carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/64—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and sulfur atoms, not being part of thio groups, bound to the same carbon skeleton
- C07C323/65—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and sulfur atoms, not being part of thio groups, bound to the same carbon skeleton containing sulfur atoms of sulfone or sulfoxide groups bound to the carbon skeleton
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
- C07C2601/08—Systems containing only non-condensed rings with a five-membered ring the ring being saturated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Description
本出願は、2008年8月19日に出願された米国仮出願番号61/090,045に対する権利を主張する。本発明は、α,β−不飽和カルボニルまたはスルホニル化合物にナトリウムまたはカリウムチオレートを添加するための改善された方法に関する。
本発明は、式Iのアルキルチオ置換アルデヒド類、ケトン類、エステル類及びスルホン類を調製するための改善された方法であって:
ここで、
EはCOまたはSO2を表し、
R1は、EがCOの場合はH、C1−C8アルキル、C1−C8アルコキシまたはアリールを表し、EがSO2の場合はC1−C8アルキルまたはアリールを表し、
R2、R3、R4及びR5はそれぞれ独立してH、C1−C8アルキルまたはアリールを表し、
該方法は、C1−C4アルカンカルボン酸及び水の存在下、式IIのα,β−不飽和カルボニルまたはスルホニル化合物と:
(ここで、E、R1、R2、R3及びR4は前述の通り)
式IIIのナトリウムまたはカリウムチオレートと:
R5S− Na+ または K+ (III)
(ここで、R5は前述の通り)
を反応させる工程を含む方法に関する。好ましくは、EはCO、R1はH、R2はH、CH3またはCH2CH3、R3はCH3またはCH2CH3、R4はH、そしてR5はCH3である。該方法は、共溶媒を用いて、または用いずに行って良い。
他に特に限定が無ければ、本明細書に記載の用語「アルキル」(「アルカン」及び「アルコキシ」等の派生語を含む)は、直鎖、分岐鎖及び環状基を含む。よって、典型的なC1−C4アルキル基は、メチル、エチル、1−メチルエチル、プロピル、1,1−ジメチルエチル、1−メチルプロピル、2−メチルプロピル、シクルプロピル及びシクロブチルである。C5−C8アルキル基は更に、ペンチル、ヘキシル、ヘプチル、オクチル、シクロペンチル、シクロヘキシル、1−メチルヘキシル、2−エチルヘキシル及び1−メチルヘプチルを含むがこれらに限定されない。
以下の説明で「実施例6」、「実施例7」、「実施例9」、「実施例10」および「実施例11」は「参考例」と読み替える。
Claims (1)
- 式Iのアルキルチオ置換アルデヒド類、ケトン類、エステル類及びスルホン類を調製する方法であって:
ここで、
EはCOまたはSO2を表し、
R1は、EがCOの場合はH、C1−C8アルキル、C1−C8アルコキシまたはアリールを表し、EがSO2の場合はC1−C8アルキルまたはアリールを表し、
R2、R3、及びR4 はそれぞれ独立してH、C1−C8アルキルまたはアリールを表し、R 5 はC 1 −C 8 アルキルまたはアリールを表し
該方法は、C1−C4アルカンカルボン酸及び水の存在下、式IIのα,β−不飽和カルボニルまたはスルホニル化合物と:
(ここで、E、R1、R2、R3及びR4は前述の通り)
式IIIのナトリウムまたはカリウムチオレートと:
R5S− Na+ または K+ (III)
(ここで、R5は前述の通り)
を反応させる工程を含む、方法。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US9004508P | 2008-08-19 | 2008-08-19 | |
US61/090,045 | 2008-08-19 | ||
PCT/US2009/053061 WO2010021855A1 (en) | 2008-08-19 | 2009-08-07 | Improved process for the addition of thiolates to alfa, beta-unsaturated carbonyl or sulfonyl compounds |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2012500265A JP2012500265A (ja) | 2012-01-05 |
JP5320465B2 true JP5320465B2 (ja) | 2013-10-23 |
Family
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Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2011523859A Active JP5320465B2 (ja) | 2008-08-19 | 2009-08-07 | α,β−不飽和カルボニルまたはスルホニル化合物にチオレート類を添加するための改善された方法 |
Country Status (13)
Country | Link |
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US (1) | US8101803B2 (ja) |
EP (1) | EP2321270B1 (ja) |
JP (1) | JP5320465B2 (ja) |
KR (1) | KR101425260B1 (ja) |
CN (1) | CN102186814B (ja) |
AU (1) | AU2009283076B2 (ja) |
BR (1) | BRPI0917511B8 (ja) |
CA (1) | CA2733544C (ja) |
IL (1) | IL211266A (ja) |
MX (1) | MX2011001869A (ja) |
PL (1) | PL2321270T3 (ja) |
WO (1) | WO2010021855A1 (ja) |
ZA (1) | ZA201101165B (ja) |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
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JP2012136466A (ja) * | 2010-12-27 | 2012-07-19 | Sumitomo Chemical Co Ltd | 2−オキソ−4−メチルチオブタン酸又はその塩の製造方法 |
WO2015169847A1 (en) | 2014-05-06 | 2015-11-12 | Veterinærinstituttet | A method for trichothecene detoxification |
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DE855704C (de) | 1943-03-27 | 1952-11-17 | Chemische Werke Huels G M B H | Verfahren zur Herstellung von schwefelhaltigen Verbindungen |
FR976673A (fr) | 1948-10-11 | 1951-03-21 | M Le Ministre De L Ind Et Du C | Procédé de préparation de produits beta-thioalcoylés |
JPS4924454B1 (ja) * | 1970-05-23 | 1974-06-22 | ||
CH556145A (fr) | 1972-08-02 | 1974-11-29 | Firmenich & Cie | Utilisation de certains derives soufres comme ingredients parfumants et/ou aromatisants. |
US4107209A (en) * | 1977-03-03 | 1978-08-15 | International Flavors & Fragrances Inc. | 1-[3-(Methylthio)butyryl]-2,6,6-trimethyl-cyclohexene and the 1,3-cyclohexadiene analog |
WO1987001699A1 (en) | 1985-08-23 | 1987-03-26 | Chevron Research Company | 2- ad1-(3-chloroallyloxyamino)alkyledene bd-5-alkylthioalkyl-cyclohexane-1,3-dione herbicides |
JPH078850B2 (ja) * | 1986-09-18 | 1995-02-01 | 三菱油化株式会社 | ペンタエリスリト−ル−テトラキス(3−アルキルチオ−プロピオネ−ト)の製造方法 |
US4944853A (en) | 1989-09-11 | 1990-07-31 | Pennwalt Corporation | Photochemical preparation of 3-(organothio) aldehydes |
US5905171A (en) * | 1995-06-22 | 1999-05-18 | Novus International, Inc. | Process for the preparation of 3-(methylthio)propanal |
AR002174A1 (es) | 1995-06-07 | 1998-01-07 | Novus Int Inc | Proceso para la preparacion de 3-(metiltio)propanal y 2-hidroxi-4-metiltio) butanonitrilo |
US5663409A (en) | 1995-06-07 | 1997-09-02 | Novus International, Inc. | Process for the preparation of 3-(methylthio) propanal and 2-hydroxy-4-(methylthio) butanenitrile |
JPH10175907A (ja) * | 1996-01-31 | 1998-06-30 | Nippon Kayaku Co Ltd | 2,3−ジ置換シクロペンタノンの医薬用途、該化合物の製造法及び新規化合物 |
US5973200A (en) * | 1997-01-23 | 1999-10-26 | Novus International, Inc. | Process for the preparation of 2-hydroxy-4-(methylthio) butanoic acid or methionine by mercaptan addition |
JPH11100345A (ja) * | 1997-09-29 | 1999-04-13 | Sumitomo Chem Co Ltd | β−置換ケトンの製造法 |
JP4186572B2 (ja) * | 2002-09-27 | 2008-11-26 | 住友化学株式会社 | 3−メチルチオプロパナールの製造方法 |
CN1616421A (zh) * | 2003-11-14 | 2005-05-18 | 上海香料研究所 | 3-甲硫基己醛的合成方法 |
WO2006060029A2 (en) | 2004-04-08 | 2006-06-08 | Dow Agrosciences Llc | Insecticidal n-substituted sulfoximines |
TWI398433B (zh) * | 2006-02-10 | 2013-06-11 | Dow Agrosciences Llc | 殺蟲性之n-取代(6-鹵烷基吡啶-3-基)烷基磺醯亞胺 |
TWI383973B (zh) | 2006-08-07 | 2013-02-01 | Dow Agrosciences Llc | 用於製備2-取代-5-(1-烷硫基)烷基吡啶之方法 |
EP2052612A1 (de) | 2007-10-24 | 2009-04-29 | Bayer CropScience AG | Herbizid-Kombination |
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Also Published As
Publication number | Publication date |
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CA2733544A1 (en) | 2010-02-25 |
CN102186814B (zh) | 2014-10-01 |
JP2012500265A (ja) | 2012-01-05 |
BRPI0917511B1 (pt) | 2021-03-30 |
CA2733544C (en) | 2013-12-17 |
PL2321270T3 (pl) | 2016-09-30 |
ZA201101165B (en) | 2012-05-30 |
IL211266A0 (en) | 2011-04-28 |
WO2010021855A1 (en) | 2010-02-25 |
EP2321270A1 (en) | 2011-05-18 |
CN102186814A (zh) | 2011-09-14 |
IL211266A (en) | 2016-04-21 |
KR101425260B1 (ko) | 2014-08-01 |
AU2009283076B2 (en) | 2012-03-08 |
EP2321270B1 (en) | 2016-03-23 |
BRPI0917511A2 (pt) | 2020-09-15 |
US8101803B2 (en) | 2012-01-24 |
KR20110044310A (ko) | 2011-04-28 |
BRPI0917511B8 (pt) | 2022-10-11 |
AU2009283076A1 (en) | 2010-02-25 |
US20100048939A1 (en) | 2010-02-25 |
MX2011001869A (es) | 2011-08-15 |
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