UST104301I4 - Process for producing pyrethroid intermediates - Google Patents

Process for producing pyrethroid intermediates Download PDF

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Publication number
UST104301I4
UST104301I4 US06/541,403 US54140383A UST104301I4 US T104301 I4 UST104301 I4 US T104301I4 US 54140383 A US54140383 A US 54140383A US T104301 I4 UST104301 I4 US T104301I4
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US
United States
Prior art keywords
compound
lithium
sodium
pyrethroid
biphenyl
Prior art date
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Pending
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US06/541,403
Inventor
Raymond M. Palmere
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FMC Corp
Original Assignee
FMC Corp
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Filing date
Publication date
Application filed by FMC Corp filed Critical FMC Corp
Priority to US06/541,403 priority Critical patent/UST104301I4/en
Assigned to FMC CORPORATION, A DE CORP. reassignment FMC CORPORATION, A DE CORP. ASSIGNMENT OF ASSIGNORS INTEREST. Assignors: PALMERE, RAYMOND M.
Application granted granted Critical
Publication of UST104301I4 publication Critical patent/UST104301I4/en
Pending legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C25/00—Compounds containing at least one halogen atom bound to a six-membered aromatic ring
    • C07C25/18—Polycyclic aromatic halogenated hydrocarbons
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
    • C07C209/62—Preparation of compounds containing amino groups bound to a carbon skeleton by cleaving carbon-to-nitrogen, sulfur-to-nitrogen, or phosphorus-to-nitrogen bonds, e.g. hydrolysis of amides, N-dealkylation of amines or quaternary ammonium compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C22/00—Cyclic compounds containing halogen atoms bound to an acyclic carbon atom
    • C07C22/02—Cyclic compounds containing halogen atoms bound to an acyclic carbon atom having unsaturation in the rings
    • C07C22/04—Cyclic compounds containing halogen atoms bound to an acyclic carbon atom having unsaturation in the rings containing six-membered aromatic rings

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

Abstract

Disclosed is a process for the preparation of an optionally substituted N,N-2-trimethyl-[1,1'-biphenyl]-3-methanamine, Compound II, by rearrangement of a N,N,N-trimethyl-]1,1'-biphenyl]-2-methanaminium compound, Compound I. Compound I is treated with at least one equivalent of sodium or lithium methylsulfinyl carbanion in the presence of dimethylsulfoxide at a temperature in the range of 0° to 70° C. to give Compound II. The process is conveniently conducted by adding lithium hydride or sodium hydride to excess dimethylsulfoxide to produce a solution of the lithium or sodium methylsulfinyl carbanion, then adding Compound I to the solution thus formed.
Compound II is a useful intermediate for the preparation of insecticidal pyrethroid esters of formula IV. Compound II may be converted into ester IV by treatment with ethyl chloroformate or cyanogen bromide to give intermediate III, followed by reaction with an alkali metal or ammonium salt of the desired pyrethroid acid.
In the following formulas, R and R1 are independently halogen, alkyl, fluoromethyl, alkoxy, or fluoroalkoxy, m is 0 to 3, n is 0 to 5, Y is a chloride, bromide, iodide, or hydroxide ion, X is chlorine or bromine, and R2 CO2 is a pyrethroid acid moiety. ##STR1##
US06/541,403 1983-10-13 1983-10-13 Process for producing pyrethroid intermediates Pending UST104301I4 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
US06/541,403 UST104301I4 (en) 1983-10-13 1983-10-13 Process for producing pyrethroid intermediates

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US06/541,403 UST104301I4 (en) 1983-10-13 1983-10-13 Process for producing pyrethroid intermediates

Publications (1)

Publication Number Publication Date
UST104301I4 true UST104301I4 (en) 1984-06-05

Family

ID=24159454

Family Applications (1)

Application Number Title Priority Date Filing Date
US06/541,403 Pending UST104301I4 (en) 1983-10-13 1983-10-13 Process for producing pyrethroid intermediates

Country Status (1)

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US (1) UST104301I4 (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN109180500A (en) * 2018-09-05 2019-01-11 常州大学 A kind of preparation method of N, N- dimethyl -1- alkyl biphenyl methylamine

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN109180500A (en) * 2018-09-05 2019-01-11 常州大学 A kind of preparation method of N, N- dimethyl -1- alkyl biphenyl methylamine

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