UST104301I4 - Process for producing pyrethroid intermediates - Google Patents
Process for producing pyrethroid intermediates Download PDFInfo
- 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
- Authority
- US
- United States
- Prior art keywords
- compound
- lithium
- sodium
- pyrethroid
- biphenyl
- 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.)
- Pending
Links
- 239000002728 pyrethroid Substances 0.000 title abstract 4
- 238000000034 method Methods 0.000 title abstract 3
- 239000000543 intermediate Substances 0.000 title 1
- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 abstract 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 abstract 4
- 150000001875 compounds Chemical class 0.000 abstract 3
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 abstract 2
- 150000002148 esters Chemical class 0.000 abstract 2
- 229910052744 lithium Inorganic materials 0.000 abstract 2
- 229910052708 sodium Inorganic materials 0.000 abstract 2
- 239000011734 sodium Substances 0.000 abstract 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 abstract 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 abstract 1
- 101100386054 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) CYS3 gene Proteins 0.000 abstract 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 150000001340 alkali metals Chemical class 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 150000003863 ammonium salts Chemical class 0.000 abstract 1
- 235000010290 biphenyl Nutrition 0.000 abstract 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 1
- 229910052794 bromium Chemical group 0.000 abstract 1
- 229910052801 chlorine Inorganic materials 0.000 abstract 1
- 239000000460 chlorine Substances 0.000 abstract 1
- 125000001309 chloro group Chemical group Cl* 0.000 abstract 1
- ATDGTVJJHBUTRL-UHFFFAOYSA-N cyanogen bromide Chemical compound BrC#N ATDGTVJJHBUTRL-UHFFFAOYSA-N 0.000 abstract 1
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 abstract 1
- 125000004428 fluoroalkoxy group Chemical group 0.000 abstract 1
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 abstract 1
- 230000000749 insecticidal effect Effects 0.000 abstract 1
- 229910000103 lithium hydride Inorganic materials 0.000 abstract 1
- 230000008707 rearrangement Effects 0.000 abstract 1
- 229910000104 sodium hydride Inorganic materials 0.000 abstract 1
- 239000012312 sodium hydride Substances 0.000 abstract 1
- 101150035983 str1 gene Proteins 0.000 abstract 1
Classifications
-
- 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
Landscapes
- 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##
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)
| Country | Link |
|---|---|
| US (1) | UST104301I4 (en) |
Cited By (1)
| 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 |
-
1983
- 1983-10-13 US US06/541,403 patent/UST104301I4/en active Pending
Cited By (1)
| 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 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| ES482773A1 (en) | A PROCEDURE FOR THE PREPARATION OF Z-2-ACILAMINOPROPE-NOATOS-3-MONOSUSTITUIDOS. | |
| UST104301I4 (en) | Process for producing pyrethroid intermediates | |
| JPS57109787A (en) | Pyrazoloindazole derivative | |
| ES2023157B3 (en) | PROCEDURE FOR OBTAINING TETRAFLUOROPHTHALIC ACID. | |
| JPS54112873A (en) | Preparation of 2,2,6,6-tetramethyl-4-oxopiperidine | |
| GB2001062A (en) | Preparation of Pyridinecarboxylic acid piperazides | |
| HUT46701A (en) | Process for producing alpha-amino-alkyl-phosphonic acids | |
| US3009917A (en) | Protoverine 6, 7-diacetate 15 (1) 2'-methylbutyrate and its preparation | |
| JPS55139382A (en) | Production of insect pheromone | |
| DE3173348D1 (en) | Process of producing 1,3-dithiol-2-ylidene malonic acid dialkyl esters | |
| JPS6466A (en) | Production of 2-azetidinone derivative | |
| JPS5463085A (en) | Preparation of malonic acid derivative | |
| IE31935B1 (en) | Process for the manufacture of benzodiazepine derivatives | |
| JPS5746992A (en) | Preparation of thio substituted carbamic acid derivative | |
| ATE78015T1 (en) | PROCESS FOR THE PREPARATION OF 3-PHENYL-2METHYLPROPANOL AND ITS P-SUBSTITUTED ALKYL DERIVATIVES. | |
| JPS5687590A (en) | Diphosphoglycerine derivative | |
| EP0357792A4 (en) | Process for preparing pyridine-2,3-dicarboxylic acid compounds | |
| JPS5795924A (en) | Preparation of allyl-type chloride | |
| JPS56138141A (en) | Carboxylic acid ester, its preparation and insecticidal and micidal agent | |
| JPS55108857A (en) | Preparation of 5-fluorouracil derivative | |
| JPS5479247A (en) | Para-substituted phenylacetic acid derivative and its preparation | |
| JPS55144000A (en) | Preparation of 2-amino-adenosine-3',5'-cyclic phosphoric acid | |
| JPS56135437A (en) | Preparation of substituted phenol | |
| FR2587334B1 (en) | PROCESS FOR THE PREPARATION OF BROMOFLUORO-ACETIC ACIDS | |
| JPS5746948A (en) | Production of beta- 1,2,2,-trifluoro-2-alkoxyethyl alanine derivative |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| STPP | Information on status: patent application and granting procedure in general |
Free format text: DEFENSIVE PUBLICATION OR SIR FILE |