WO1992012127A1 - Nouveau compose de disulfure - Google Patents

Nouveau compose de disulfure Download PDF

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Publication number
WO1992012127A1
WO1992012127A1 PCT/JP1991/001773 JP9101773W WO9212127A1 WO 1992012127 A1 WO1992012127 A1 WO 1992012127A1 JP 9101773 W JP9101773 W JP 9101773W WO 9212127 A1 WO9212127 A1 WO 9212127A1
Authority
WO
WIPO (PCT)
Prior art keywords
chloro
disulfide
compound
mouth
bis
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.)
Ceased
Application number
PCT/JP1991/001773
Other languages
English (en)
French (fr)
Japanese (ja)
Inventor
Hideo Ohi
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Ihara Chemical Industry Co Ltd
Original Assignee
Ihara Chemical Industry Co Ltd
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 Ihara Chemical Industry Co Ltd filed Critical Ihara Chemical Industry Co Ltd
Priority to EP92901901A priority Critical patent/EP0517924B1/en
Priority to DE69118175T priority patent/DE69118175T2/de
Priority to KR1019920702073A priority patent/KR0156869B1/ko
Publication of WO1992012127A1 publication Critical patent/WO1992012127A1/ja
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • 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
    • C07C323/23—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 nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
    • C07C323/39—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 nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton at least one of the nitrogen atoms being part of any of the groups, X being a hetero atom, Y being any atom
    • C07C323/40—Y being a hydrogen or a carbon atom
    • C07C323/41—Y being a hydrogen or an acyclic carbon atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C319/00—Preparation of thiols, sulfides, hydropolysulfides or polysulfides
    • C07C319/02—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of thiols
    • C07C319/06—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of thiols from sulfides, hydropolysulfides or polysulfides

Definitions

  • the present invention provides thiadiazabicyclononane-based pesticides, for example, bis- (5-acetamino-2-chloro- 4-fluorobenzene) disulfide, which is useful as an intermediate material for herbicides.
  • thiadiazabicyclononane drugs examples include, for example,
  • the compound has the following structure and is used as an active substance of a herbicide (see JP-A-63-264489).
  • the compound is also represented as compound (2).
  • the diazotization operation is complicated and the yield is low, and the nitration is also mainly caused by side reactions, and the yield is low.
  • the results are not inferior and are not always a good method.
  • the present invention solves the above-mentioned disadvantages of the prior art, and can be easily and in high yield to 5-amino-2-chloro-4-fluoro-mouth-thiophenol represented by the formula (3).
  • the purpose of the present invention is to provide a novel disulfide compound.
  • the present invention provides a bis- (5-acetamino-2-chloro-4-4-fluorobenzene) disulfide compound represented by the formula:
  • the operation for obtaining the disulfide compound of the present invention is carried out in the presence of a Lewis acid in 4-chloro -Reaction of 2-fluoroacetanilide (4) with monochlorochloride at 0-100'C, preferably 20-50'C.
  • Lewis acid used in the above operation for example, aluminum chloride, iron chloride, zinc chloride and the like can be mentioned. Among them, use of aluminum chloride which can be obtained in high yield is preferable.
  • a solvent may be used as long as it is inert to the reaction, in order to smoothly progress the reaction.
  • a solvent for example, an organic solvent such as a halogenated hydrocarbon is preferable, and dichloromethane, ⁇ -open-form, dichloroethane, etc. may be used.
  • the amount of sulfur monochloride used in the above operation is 0.5 mol or more, preferably 0.6 to 2.5 times mol based on compound (4), and the amount of Lewis acid used is 1 to 5 times the molar amount based on the compound (4), preferably 2 to 2.5 times the molar amount.
  • an organic solvent it is sufficient that the amount is not less than that which can be stirred.
  • 4-chloro-2-fluoroacetanilide (4) used as a raw material can be easily obtained by a method for acylating anilines described in JP-A-51-51521. be able to. ⁇
  • the disulfide compound (1) of the present invention obtained as described above is reduced with metallic zinc in acetic acid, and further hydrolyzed with an aqueous alkali solution to give 5-amino-2-chloride.
  • Lolo-4-fluoro-thiophenol (3) can be induced.
  • the 5-amino-2-chloro-4-fluoro-thiophenol (3) is an active compound of a thiadiazabicyclononan herbicide described in JP-A-63-264489, as shown below. Can be guided to
  • the present invention relates to a novel bis- (5-acetamino-2-chloride) by reacting 4-chloro-2-fluoroacetanilide (4) with sulfur monochloride in the presence of a Lewis acid. -4-full-year-old benzene) disulfide (1).
  • the disulfide compound (1) of the present invention can be converted to 5-amino-2-chloro-4-fluoro-thiophenol (3) by reduction and hydrolysis. Can be.
  • the present invention can be a useful intermediate of a thiadiazabicyclononane compound having a herbicidal activity described in JP-A-63-264489.
  • reaction solution was poured into 200 g of ice water, and the organic layer was extracted with 150 ml of ethyl acetate.After drying, the solvent, dichloromethane and ethyl acetate, was distilled off under reduced pressure. The residue was washed with ethyl acetate to give 7.4 g of bis- (5-acetamino-2-chloro-4--4-fluorobenzene) disulfide (1). The yield was 84.7%.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
PCT/JP1991/001773 1990-12-27 1991-12-26 Nouveau compose de disulfure Ceased WO1992012127A1 (fr)

Priority Applications (3)

Application Number Priority Date Filing Date Title
EP92901901A EP0517924B1 (en) 1990-12-27 1991-12-26 Novel disulfide compound
DE69118175T DE69118175T2 (de) 1990-12-27 1991-12-26 Neues disulfidderivat
KR1019920702073A KR0156869B1 (ko) 1990-12-27 1991-12-26 신규 디술피드 화합물

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP41678590A JP3172878B2 (ja) 1990-12-27 1990-12-27 新規なジスルフィド化合物
JP2/416785 1990-12-27

Publications (1)

Publication Number Publication Date
WO1992012127A1 true WO1992012127A1 (fr) 1992-07-23

Family

ID=18524975

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP1991/001773 Ceased WO1992012127A1 (fr) 1990-12-27 1991-12-26 Nouveau compose de disulfure

Country Status (8)

Country Link
US (1) US5248822A (enExample)
EP (1) EP0517924B1 (enExample)
JP (1) JP3172878B2 (enExample)
KR (1) KR0156869B1 (enExample)
DE (1) DE69118175T2 (enExample)
ES (1) ES2087514T3 (enExample)
TW (1) TW198015B (enExample)
WO (1) WO1992012127A1 (enExample)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP3332561B2 (ja) * 1994-03-17 2002-10-07 イハラケミカル工業株式会社 チオアリール化合物の製造方法
TWI623520B (zh) * 2012-12-12 2018-05-11 德商拜耳作物科學股份有限公司 製備雙（３－胺基苯基）二硫化物及３－胺基硫醇之方法
TWI730297B (zh) * 2018-02-27 2021-06-11 日商組合化學工業股份有限公司 巰基酚化合物的製造方法及巰基酚化合物的中間體

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS60172958A (ja) * 1984-02-17 1985-09-06 Sumitomo Chem Co Ltd フエニルチオグリコ−ル酸誘導体およびその製造法
JPS6233148A (ja) * 1985-08-06 1987-02-13 Sumitomo Chem Co Ltd ベンゼンスルホニルクロリド誘導体の製造方法
JPH02221254A (ja) * 1989-02-23 1990-09-04 Nissan Chem Ind Ltd ビス―（４―フルオロ―２―クロルフェニル）ジスルフィド誘導体

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4613675A (en) * 1984-11-30 1986-09-23 Sandoz Ltd. Phosphorus containing 1-cyclohexene-1,2-dicarboxamides
JPH06233148A (ja) * 1993-01-29 1994-08-19 Victor Co Of Japan Ltd 高圧安定化回路

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS60172958A (ja) * 1984-02-17 1985-09-06 Sumitomo Chem Co Ltd フエニルチオグリコ−ル酸誘導体およびその製造法
JPS6233148A (ja) * 1985-08-06 1987-02-13 Sumitomo Chem Co Ltd ベンゼンスルホニルクロリド誘導体の製造方法
JPH02221254A (ja) * 1989-02-23 1990-09-04 Nissan Chem Ind Ltd ビス―（４―フルオロ―２―クロルフェニル）ジスルフィド誘導体

Also Published As

Publication number Publication date
JPH0616620A (ja) 1994-01-25
ES2087514T3 (es) 1996-07-16
DE69118175T2 (de) 1996-10-02
KR0156869B1 (ko) 1998-12-01
DE69118175D1 (de) 1996-04-25
EP0517924B1 (en) 1996-03-20
EP0517924A4 (en) 1993-12-15
US5248822A (en) 1993-09-28
JP3172878B2 (ja) 2001-06-04
KR930700433A (ko) 1993-03-15
EP0517924A1 (en) 1992-12-16
TW198015B (enExample) 1993-01-11

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