KR940011436A - 플루오로알킬(렌) 그룹을 함유하는 o-페닐렌디아민 - Google Patents

플루오로알킬(렌) 그룹을 함유하는 o-페닐렌디아민 Download PDF

Info

Publication number
KR940011436A
KR940011436A KR1019930023401A KR930023401A KR940011436A KR 940011436 A KR940011436 A KR 940011436A KR 1019930023401 A KR1019930023401 A KR 1019930023401A KR 930023401 A KR930023401 A KR 930023401A KR 940011436 A KR940011436 A KR 940011436A
Authority
KR
South Korea
Prior art keywords
group
ene
fluoroalkyl
alkyl
general formula
Prior art date
Application number
KR1019930023401A
Other languages
English (en)
Other versions
KR100353329B1 (ko
Inventor
마르홀트 알브레흐트
바스너 베른트
리브 폴커
Original Assignee
만프레드 조벨, 요아힘 그렘
바이엘 아크티엔게젤샤프트
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 만프레드 조벨, 요아힘 그렘, 바이엘 아크티엔게젤샤프트 filed Critical 만프레드 조벨, 요아힘 그렘
Publication of KR940011436A publication Critical patent/KR940011436A/ko
Application granted granted Critical
Publication of KR100353329B1 publication Critical patent/KR100353329B1/ko

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
    • C07C323/50—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 carboxyl groups bound to the same carbon skeleton
    • C07C323/62—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 carboxyl groups bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton
    • C07C323/63—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 carboxyl groups bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton the carbon skeleton being further substituted by nitrogen atoms, not being part of nitro or nitroso groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C211/00—Compounds containing amino groups bound to a carbon skeleton
    • C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
    • C07C211/44—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to only one six-membered aromatic ring
    • C07C211/49—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to only one six-membered aromatic ring having at least two amino groups bound to the carbon skeleton
    • C07C211/50—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to only one six-membered aromatic ring having at least two amino groups bound to the carbon skeleton with at least two amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
    • C07C211/51—Phenylenediamines
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C211/00—Compounds containing amino groups bound to a carbon skeleton
    • C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
    • C07C211/44—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to only one six-membered aromatic ring
    • C07C211/52—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to only one six-membered aromatic ring the carbon skeleton being further substituted by halogen atoms or by nitro or nitroso groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
    • C07C217/78—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton
    • C07C217/80—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings
    • C07C217/82—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings of the same non-condensed six-membered aromatic ring
    • C07C217/84—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings of the same non-condensed six-membered aromatic ring the oxygen atom of at least one of the etherified hydroxy groups being further bound to an acyclic carbon atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
    • C07C217/78—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton
    • C07C217/80—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings
    • C07C217/82—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings of the same non-condensed six-membered aromatic ring
    • C07C217/90—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings of the same non-condensed six-membered aromatic ring the oxygen atom of at least one of the etherified hydroxy groups being further bound to a carbon atom of a six-membered aromatic ring, e.g. amino-diphenylethers
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
    • C07C229/52—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton
    • C07C229/54—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton with amino and carboxyl groups bound to carbon atoms of the same non-condensed six-membered aromatic ring
    • C07C229/56—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton with amino and carboxyl groups bound to carbon atoms of the same non-condensed six-membered aromatic ring with amino and carboxyl groups bound in ortho-position
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
    • C07C229/52—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton
    • C07C229/54—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton with amino and carboxyl groups bound to carbon atoms of the same non-condensed six-membered aromatic ring
    • C07C229/60—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton with amino and carboxyl groups bound to carbon atoms of the same non-condensed six-membered aromatic ring with amino and carboxyl groups bound in meta- or para- positions
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
    • C07C229/52—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton
    • C07C229/54—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton with amino and carboxyl groups bound to carbon atoms of the same non-condensed six-membered aromatic ring
    • C07C229/64—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton with amino and carboxyl groups bound to carbon atoms of the same non-condensed six-membered aromatic ring the carbon skeleton being further substituted by singly-bound oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • C07C255/49—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
    • C07C255/58—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing cyano groups and singly-bound nitrogen atoms, not being further bound to other hetero atoms, bound to the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C317/00—Sulfones; Sulfoxides
    • C07C317/26—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
    • C07C317/32—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton with sulfone or sulfoxide groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
    • C07C317/34—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton with sulfone or sulfoxide groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having sulfone or sulfoxide groups and amino groups bound to carbon atoms of six-membered aromatic rings being part of the same non-condensed ring or of a condensed ring system containing that ring
    • C07C317/36—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton with sulfone or sulfoxide groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having sulfone or sulfoxide groups and amino groups bound to carbon atoms of six-membered aromatic rings being part of the same non-condensed ring or of a condensed ring system containing that ring with the nitrogen atoms of the amino groups bound to hydrogen atoms or to carbon atoms
    • 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
    • C07C323/31—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 having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton
    • C07C323/33—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 having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton having at least one of the nitrogen atoms bound to a carbon atom of the same non-condensed six-membered aromatic ring
    • C07C323/35—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 having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton having at least one of the nitrogen atoms bound to a carbon atom of the same non-condensed six-membered aromatic ring the thio group being a sulfide group
    • C07C323/36—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 having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton having at least one of the nitrogen atoms bound to a carbon atom of the same non-condensed six-membered aromatic ring the thio group being a sulfide group the sulfur atom of the sulfide group being further bound to an acyclic carbon atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
    • C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
    • C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
    • C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
    • C07D235/10—Radicals substituted by halogen atoms or nitro radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D319/10—1,4-Dioxanes; Hydrogenated 1,4-dioxanes
    • C07D319/14—1,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems
    • C07D319/16—1,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems condensed with one six-membered ring
    • C07D319/20—1,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems condensed with one six-membered ring with substituents attached to the hetero ring

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

본 발명은 플루오로알킬(렌)그룹을 함유하는 일반식(Ⅰ)의 신규한 o-페닐렌디아민, 이의 제조방법 및 중간체로서의 이의 용도에 관한 것이다.
상기식에서, 사용된 기호는 명세서에서 정의한 바와 같다.

Description

플루오로알킬(렌)그룹을 함유하는 o-페닐렌디아민
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음

Claims (10)

  1. EP-A제251,013호 및 EP-A제487,286호에 기술된 화합물을 제외한, 플루오로알킬(렌)그룹을 함유하는 일반식(I)의 o-페닐렌디아민.
    상기식에서, R1은 CF3;OCF3;SCF3; 직쇄이거나 측쇄일 수 있으며 불소, N(CF3)2, 4위치에 CF3또는 CN을 함유하는 페닐 또는 페녹시 라디칼 및, 필요한 경우, 독립적으로 추가의 치환체, 1,1,2,3,3,3-헥사플루오로프로폭시, 1,1,2-트리플루오로-2-클로로-에톡시, 1,1,2,2-테트라플루오로에톡시, 1,1,2-트리플루오로-2-클로로-에틸티오 또는 1,1,2,3,3,3-헥사플루오로프로필티오로에 의해 부분적으로 또는 완전히 치환되는 SO2-C1-C6-알킬을 나타내고, R2은 F;Cl;Br;CN;CH3;OCF3;직쇄이거나 측쇄일 수 있으며, 불소, COO-C1-C6-알킬, COOC6H5, 1,1,2,2-테트라플루오로에톡시, 1,1,2,3,3-헥사플루오로프로폭시 또는 1,1,2-트리플루오로-2-클로로-에톡시에 의해 부분적으로 또는 완전히 치환될 수 있는 SO2-C1-C6-알킬을 나타내며, R3는 수소 COCH3또는 COCF3를 나타내고, 또한 R1및 R2는 함께 -O-CFCl-CFCl-0-라디칼을 나타낼 수 있다.
  2. 제1항에 있어서, R3가 수소를 나타내며, 라디칼 R1및 R2가 각각의 경우에 주어진 위치에서 하기 정의와 같음을 특징으로 하는, 플루오로알킬(렌) 그룹을 함유하는 o-페닐렌디아민.
  3. 플루오로알킬렌 그룹을 함유하는 일반식(I′)의 o-페닐렌디아민.
    상기식에서, R3는 제1항에서 정의한 바와 같다.
  4. 일반식(Ⅱ)의 벤젠 유도체를 디니트로화시키고, 니트로 그룹을 환원시켜 R1및 R2가 아미노 그룹에 대해 4 및 5 위치에서 존재하며 하기 언급하는 D1및 D2의 의미를 갖는 일반식(Ⅰ)의 화합물을 수득함을 특징으로 하여, R1및 R2가 각각 아미노 그룹에 대해 4 및 5 위치에서 공여체 그룹을 나타내고 R3가 수소를 나타내는, 플루오로알킬(렌) 그룹을 함유하는 제1항의 o-페닐렌디아민을 제조하는 방법.
    상기식에서, D1는 CF3O, CF3S, CH2CF20, CHFCl-CF2O, CF3CHFCF2O, CF3CF20, CF3CF2CF2O, CF3CF2S 또는 CF3CHFCF2O를 나타내고, D2는 CF3O, CF3S, CH2CF20, CHFCl-CF2O, CF3CHF-CF2O, CF3CF20, CF3CF2CF2O, CF3CF2S, CF3CHFCF2O, 붕소, 염소, 브롬, C1-C6-알킬 또는 C1-C6-알콕시를 나타낸다.
  5. 제4항에 있어서, 디니트로화 반응을, 필요할 경우 올레움을 함유하는, HNO3/H2SO4혼합물을 사용하여 0 내지 100℃의 온도에서 수행하고, 환원반응을 수성 염산 및 에탄올 존재하에 철을 사용하여 50 내지 100℃에서 수행하거나 주기율표의 Ⅷ아족으로부터 금속 또는 금속 화합물 존재하에 25 내지 100℃ 및 1 내지 50바에서 수소원자를 사용하여 촉매적으로 수행함을 특징으로 하는 방법.
  6. 일반식(Ⅲ)의 니트로벤젠 유도체를 암모니아와 반응시켜, Hal 그룹을 아미노 그룹으로 치환시키고 이렇게 하여 수득한 니트로아닐린을 환원시킴을 특징으로 하여, R1이 제1항에서 정의한 바와 같고 아미노 그룹에 대해 4위치에 존재하며, R2가 아미노 그룹에 대해 5위치에서 Cl 또는 Br을 나타내며 R3가 수소를 나타내는, 플루오로알킬(렌) 그룹을 함유하는 제1항의 o-페닐렌디아민을 제조하는 방법.
    상기식에서, R1은 일반식(I)에서 정의한 바와 같고, Ha1은 불소, 염소 또는 브롬을 나타낸다.
  7. 제6항에 있어서, 암모니아와의 반응을 압력 용기내에서 물과 테트라알킬암모늄 염의 존재하에 80 내지 200℃의 온도에서 액체 암모니아를 사용하여 수행하고 환원반응을 제5항에서와 유사하게 수행함을 특징으로 하는 방법.
  8. 일반식(Ⅳ)의 니트로아닐린을 염소화 또는 브롬화제와 반응시킨 후 니트로 그룹을 환원시킴을 특징으로 하여, R1이 제1항에서 정의한 바와 같고, R2가 아미노 그룹에 대해 6 위치에서 Cl 또는 Br을 나타내고, R3가 수소를 나타내는, 플루오로알킬(렌) 그룹을 함유하는 제1항의 o-페닐렌디아민을 제조하는 방법.
    상기식에서, R1은 제1항에서 정의한 바와 같다.
  9. 일반식(Ⅴ)의 벤젠 유도체를 모노니트로화시키고 NO2그룹을 NH2그룹으로 환원시킨 다음, NH2그룹을 아실화시키고, 생성된 화합물을 다시 모노니트로화시킨 다음 이 NO2그룹을 다시 NH2그룹으로 환원시킴을 특징으로 하여, R1이 두 아미노 그룹에 대해 4위치에서 공여체 그룹을 나타내고, R2가 수용체 그룹을 나타내며, R3가 수소가 아닌, 플루오로알킬(렌) 그룹을 함유하는 일반식(Ⅰ)의 o-페닐렌디아민을 제조하는 방법.
    상기식에서, D1은 제4항에서 정의한 바와 같고, A는 CF3, 직쇄이거나 또는 측쇄일 수 있으며 불소, COO-C1-C6-알킬 또는 CN에 의해 부분적으로 또는 완전히 치환될 수 있는 SO2-C1-C6-알킬을 나타낸다.
  10. 먼저 일반식(Ⅰ)의 물질을 트리플루오로아세트산과 반응시켜 일반식(Ⅶ)의 2-트리플루오로메틸벤즈이미다졸을 수득하고 이를 일반식(Ⅷ)의 화합물과 추가로 반응시킴으로써 일반식(Ⅶ)의 치환된 벤즈이미다졸을 제조하기 위한, R3가 수소를 나타내거나 가수분해에 의해 수소로 전환된, 플루오로알킬(렌) 그룹을 함유하는 제1항의 o-페닐렌디아민의 용도.
    상기식에서, R1및 R2는 제1항에 정의한 바와 같고, R4는 수소, 알킬, 알콕시 또는 치환되거나 비치환된 아릴을 나타내며, R5는 치환되거나 비치환된 하이드록실, 시아노 또는 알킬, 알케닐, 알키닐, 알콕시, 알케닐옥시, 알키닐옥시, 알킬티오, 아미노, 아미노카보닐, 알킬카보닐, 알콕시카보닐, 알킬카보닐옥시, 디알콕시포스포닐, (헤테로)아릴, (헤테로)아릴카보닐, (헤테로)아릴옥시카보닐, (헤테로)아릴카보닐옥시 또는 (헤테로)아릴아미노 카보닐아미노카보닐옥시를 나타내고, A는 적합한 이탈 그룹을 나타낸다.
    ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
KR1019930023401A 1992-11-06 1993-11-05 플루오로알킬또는플루오로알킬렌그룹을함유하는o-페닐렌디아민및이의제조방법 KR100353329B1 (ko)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DEP4237564.9 1992-11-06
DE4237564A DE4237564A1 (de) 1992-11-06 1992-11-06 Fluoralkyl(en)gruppen enthaltende o-Phenylendiamine

Publications (2)

Publication Number Publication Date
KR940011436A true KR940011436A (ko) 1994-06-21
KR100353329B1 KR100353329B1 (ko) 2003-04-16

Family

ID=6472304

Family Applications (1)

Application Number Title Priority Date Filing Date
KR1019930023401A KR100353329B1 (ko) 1992-11-06 1993-11-05 플루오로알킬또는플루오로알킬렌그룹을함유하는o-페닐렌디아민및이의제조방법

Country Status (7)

Country Link
US (1) US5484953A (ko)
EP (1) EP0596358B1 (ko)
JP (1) JPH0770002A (ko)
KR (1) KR100353329B1 (ko)
DE (2) DE4237564A1 (ko)
ES (1) ES2124280T3 (ko)
TW (1) TW249223B (ko)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE4415435A1 (de) * 1994-05-03 1995-11-09 Bayer Ag Benzimidazol-Derivate
US7531700B2 (en) * 2003-09-24 2009-05-12 E.I. Du Pont De Nemours And Company Fluorinated arylethers and methods for use thereof
JP2006290883A (ja) * 2005-03-17 2006-10-26 Nippon Nohyaku Co Ltd 置換ヘテロ環カルボン酸アニリド誘導体、その中間体及び農園芸用薬剤並びにその使用方法
CN103012171B (zh) * 2012-12-13 2015-07-22 上海北卡医药技术有限公司 一种4-氯-5-(三氟甲氧基)-1,2-苯二胺的制备方法
DE102016013066A1 (de) 2016-11-03 2018-05-03 Merck Patent Gmbh Fluortenside

Family Cites Families (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1163262A (en) * 1966-01-13 1969-09-04 Fisons Pest Control Ltd Substituted Benzimidazoles and Biocidally Active Compositions
DE3412079A1 (de) * 1984-03-31 1985-10-03 Bayer Ag, 5090 Leverkusen Verfahren zur herstellung von benzokondensierten, tetrachlorierten, heterocyclischen verbindungen
DE3430513A1 (de) * 1984-08-18 1986-02-27 Wella Ag, 6100 Darmstadt Haarfaerbemittel mit diamino-tetrafluorethoxybenzolen sowie neue diamino-tetrafluorethoxybenzole
FR2594437A1 (fr) * 1986-02-19 1987-08-21 Rhone Poulenc Agrochimie Nouveaux derives du cyano-2 benzimidazole, leur preparation, les compositions les contenant et leur utilisation comme fongicide
DE3621265A1 (de) * 1986-06-25 1988-01-07 Bayer Ag N-sulfenylierte 2-trifluormethyl-benzimidazole
DE3621301A1 (de) * 1986-06-25 1988-01-07 Bayer Ag 2-trifluormethyl-benzimidazole
DE3621215A1 (de) * 1986-06-25 1988-01-07 Bayer Ag Fluorhaltige o-phenylendiamine und o-aminophenole
AU638614B2 (en) * 1990-11-20 1993-07-01 Sumitomo Chemical Company, Limited Benzimidazole derivative, a method for producing the same, its intermediate compounds and an agricultural and horticultural fungicide containing the benzimidazole derivative as an active ingredient
JPH04308580A (ja) * 1991-04-05 1992-10-30 Sumitomo Chem Co Ltd ベンズイミダゾール誘導体、その製造法およびそれを有効成分とする農園芸用殺菌剤

Also Published As

Publication number Publication date
JPH0770002A (ja) 1995-03-14
EP0596358B1 (de) 1998-10-28
ES2124280T3 (es) 1999-02-01
DE59309096D1 (de) 1998-12-03
KR100353329B1 (ko) 2003-04-16
DE4237564A1 (de) 1994-05-11
US5484953A (en) 1996-01-16
EP0596358A1 (de) 1994-05-11
TW249223B (ko) 1995-06-11

Similar Documents

Publication Publication Date Title
US3817698A (en) Keratinic fiber dye compositions containing n,n'-di-nitrophenyl or nitrophenyl - anthraquinone substituted alkylene diamine dyes and the mono-quaternary ammonium salts thereof
Finnegan et al. Preparation and isomerization of 5-alkylaminotetrazoles
US3236891A (en) Nitrophenylenediamine derivatives
US4152522A (en) Process for the preparation of 2-benzimidazole carbamates
Senda et al. Pyrimidine derivatives and related compounds. 15. Synthesis and analgetic and antiinflammatory activities of 1, 3-substituted 5-amino-6-methyluracil derivatives
FI59991B (fi) Foerfarande foer framstaellning av 2-arylamino-2-imidazolin-derivat och deras salter
KR940011436A (ko) 플루오로알킬(렌) 그룹을 함유하는 o-페닐렌디아민
US4363913A (en) Preparation of 2-aminobenzothiazoles
US4150154A (en) Amidinoureas
EP1997802A1 (en) Method for nitrating isourea
D'Amico et al. Nitrosoanilines
US6194614B1 (en) Process for the preparation of benzothiazolone compounds
US3119867A (en) Amino, nitro-phenyl-biguanides and amino, nitro-phenyl; guanyl-ureas
KR910011775A (ko) 이소티오시아네이트의 제조 방법
US20130237725A1 (en) 2,5-disubstituted-1,4-diaminobenzenes
Kamel et al. Synthesis of 1-methyl-7-nitrobenzotriazole and some derivatives
Blomquist et al. BENZOTHIAZOLES. II. NUCLEAR CHLORINATION IN THE HERZ PROCESS1
US3941798A (en) 5-Alkyl-3-(2-hydroxylamino-4-chlorophenyl)-1,3,4-oxadiazolin-2-one compounds
US5371232A (en) Preparation of 2-(4-aminophenyl)benzothiazole compounds
US3775442A (en) Process for the manufacture of a triarylmethane compound
KR900009616A (ko) 5-아미노-1,2,4-트리아졸-3-설폰아미드의 제조방법
KR840000514A (ko) 벤조일- 페닐- 피페리딘 유도체의 제법
JPS60146847A (ja) 置換ベンゼン化合物のニトロ化異性体を分離する方法
US4292446A (en) Aniline derivatives
EP0701992B1 (de) Verfahren zur Herstellung nitrosubstituierter Arylamine

Legal Events

Date Code Title Description
A201 Request for examination
E902 Notification of reason for refusal
E902 Notification of reason for refusal
E701 Decision to grant or registration of patent right
GRNT Written decision to grant
LAPS Lapse due to unpaid annual fee