WO2014152453A3 - Continuous flow synthesis of dithioester compounds - Google Patents

Continuous flow synthesis of dithioester compounds Download PDF

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Publication number
WO2014152453A3
WO2014152453A3 PCT/US2014/027356 US2014027356W WO2014152453A3 WO 2014152453 A3 WO2014152453 A3 WO 2014152453A3 US 2014027356 W US2014027356 W US 2014027356W WO 2014152453 A3 WO2014152453 A3 WO 2014152453A3
Authority
WO
WIPO (PCT)
Prior art keywords
continuous flow
dithioester
compounds
flow synthesis
methods
Prior art date
Application number
PCT/US2014/027356
Other languages
French (fr)
Other versions
WO2014152453A2 (en
Inventor
Kanth Josyula
Mitesh Patel
Original Assignee
Sigma-Aldrich Co. Llc
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Sigma-Aldrich Co. Llc filed Critical Sigma-Aldrich Co. Llc
Publication of WO2014152453A2 publication Critical patent/WO2014152453A2/en
Publication of WO2014152453A3 publication Critical patent/WO2014152453A3/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C327/00—Thiocarboxylic acids
    • C07C327/36—Esters of dithiocarboxylic acids
    • 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
    • C07D213/62—Oxygen or sulfur atoms
    • C07D213/70—Sulfur atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/08—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D277/12—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member 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
    • C07D277/16—Sulfur atoms

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

The present technology relates to methods of producing various dithioester-containing compounds via continuous flow reactors. Dithioesters are an important class of compounds in synthetic chemistry, having numerous applications in pharmaceutical, applied, and other chemical industries. For example, reversible addition-fragmentation chain transfer (RAFT) polymerization is one of the most effective and versatile methods for providing living characteristics to radical polymerization.
PCT/US2014/027356 2013-03-14 2014-03-14 Continuous flow synthesis of dithioester compounds WO2014152453A2 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US201361782023P 2013-03-14 2013-03-14
US61/782,023 2013-03-14

Publications (2)

Publication Number Publication Date
WO2014152453A2 WO2014152453A2 (en) 2014-09-25
WO2014152453A3 true WO2014152453A3 (en) 2014-11-20

Family

ID=51581711

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2014/027356 WO2014152453A2 (en) 2013-03-14 2014-03-14 Continuous flow synthesis of dithioester compounds

Country Status (1)

Country Link
WO (1) WO2014152453A2 (en)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2018213627A1 (en) 2017-05-17 2018-11-22 Quadion Llc Zwitterionic monomers, polyzwitterionic polymers formed therefrom, surface functionalization and surface modification

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4252814A (en) * 1979-07-05 1981-02-24 American Cyanamid Company Ovicidal and larvicidal cyanomethyl thioesters
US20020019554A1 (en) * 2000-06-09 2002-02-14 Benicewicz Brian C. Dithiocarboxylic ester synthetic process
US6512081B1 (en) * 1997-07-21 2003-01-28 E.I. Dupont Nemours And Company Synthesis of dithioester chain transfer agents and use of bis(thioacyl) disulfides or dithioesters as chain transfer agents
US20040186302A1 (en) * 2003-03-18 2004-09-23 Rohmax Additives Gmbh Process for preparing dithioesters

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4252814A (en) * 1979-07-05 1981-02-24 American Cyanamid Company Ovicidal and larvicidal cyanomethyl thioesters
US6512081B1 (en) * 1997-07-21 2003-01-28 E.I. Dupont Nemours And Company Synthesis of dithioester chain transfer agents and use of bis(thioacyl) disulfides or dithioesters as chain transfer agents
US20020019554A1 (en) * 2000-06-09 2002-02-14 Benicewicz Brian C. Dithiocarboxylic ester synthetic process
US20040186302A1 (en) * 2003-03-18 2004-09-23 Rohmax Additives Gmbh Process for preparing dithioesters

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
FUJINAMI ET AL.: "Formation of 1,1-dithiodicarboxylic acid esters from cyclic ketones, carbon disulfide, and lithium methoxide.", CHEMISTRY LETTERS, 1982, pages 123 - 126, Retrieved from the Internet <URL:https://www.jstage.jst.go.jp/article/cl1972/11/1/11_1_123/_pdf> [retrieved on 20140825] *

Also Published As

Publication number Publication date
WO2014152453A2 (en) 2014-09-25

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