KR850006398A - Method for preparing 3-methyl-7-fluoro-5-nitrobenzothiophene - Google Patents

Method for preparing 3-methyl-7-fluoro-5-nitrobenzothiophene Download PDF

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KR850006398A
KR850006398A KR1019850001166A KR850001166A KR850006398A KR 850006398 A KR850006398 A KR 850006398A KR 1019850001166 A KR1019850001166 A KR 1019850001166A KR 850001166 A KR850001166 A KR 850001166A KR 850006398 A KR850006398 A KR 850006398A
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fluoro
acid
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융에 보도 (외 2)
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게르트 바디케, 하르트무트 클리미쉬
트로폰베르케 게엠베하 운트 캄파니, 카게
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    • C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
    • C07D333/62—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes 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 carbon atoms of the hetero ring
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    • C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
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    • C07C201/00—Preparation of esters of nitric or nitrous acid or of compounds containing nitro or nitroso groups bound to a carbon skeleton
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    • C07C205/58—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton the carbon skeleton being further substituted by halogen atoms
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    • 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
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    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C319/00—Preparation of thiols, sulfides, hydropolysulfides or polysulfides
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    • 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
    • C07C323/51—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 atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
    • C07C323/52—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 atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated
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    • C07D—HETEROCYCLIC COMPOUNDS
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Abstract

내용 없음No content

Description

3-메틸-7-플루오로-5-니트로벤조티오펜의 제조방법Method for preparing 3-methyl-7-fluoro-5-nitrobenzothiophene

본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음As this is a public information case, the full text was not included.

Claims (15)

(a) 공지의 방법에 의해서, 2-플루오로아닐린(Ⅱ)를 7-플루오로이사틴(Ⅲ)으로 전환시키고, (b) 7-플루오로이사틴(Ⅲ)을 질화시키고, 이어서 이생성물을 산화시켜서 3-플루오로-5-니트로안트라닐산(Ⅳ)를 얻고, (c)3-플루오로-5-니트로안트라닐산(Ⅳ)를 디아조화시키고, 이 디아조생성물을 염화 제1구리 존재하에서 염산과 반응시켜서 3-플루오로-2-클로로-5-니트로벤조산(Ⅴ)를 얻고, (d)상기 3-플루오로-2-클로로-5-니트로벤조산(Ⅴ)을 염화티오닐과 반응시켜서 대응하는 산염화물(Ⅵ)을 얻고, (e)상기 3-플루오로-2-클로로-5-니트로벤조일 클로라이드(Ⅵ)를 디에틸 에톡시마그네슘 말로네이트와 반응시켜서 디에틸(3-플루오로- 2-클로로-5-니트로벤조일)-말로네이트(Ⅶ)를 얻고, (f) 디에틸 (3-플루오로-2-클로로-5-니트로벤조일)-말로네이트(Ⅶ)를 황산 존재하에 프로피온산과 반응시켜서 3-플루오로-2-클로로-5-니트로아세토 페논(Ⅷ)을 얻고, (g)상기-3-플루오로-2-클로로-5-니트로아세토 페논(Ⅷ)을 메르캅토 아세토산을 사용하여 (2-아세틸-6-플루오로-4-니트로페닐티오)-아세트산(Ⅸ)로 전환시키고, (h) 상기 (2-아세틸-6-플루오로-4-니트로 페닐티오)-아세트산(Ⅸ)을 사이클화 시켜서 3-메틸-7 플루오로-5-니트로벤조티오펜(Ⅰ)을 얻는 것을 특징으로 하는 3-메틸-7-플루오로-5-니트로벤조티오펜(Ⅰ)의 제조방법.(a) converting 2-fluoroaniline (II) to 7-fluoroisatin (III) by known methods, (b) nitriding 7-fluoroisatin (III), and then oxidizing this product To obtain 3-fluoro-5-nitroanthranilic acid (IV), and (c) 3-fluoro-5-nitroanthranilic acid (IV) to diazotize, and this diazo product is hydrochloric acid in the presence of cuprous chloride. To 3-fluoro-2-chloro-5-nitrobenzoic acid (V), and (d) reacting the 3-fluoro-2-chloro-5-nitrobenzoic acid (V) with thionyl chloride to react. To an acid chloride (VI), and (e) reacting the 3-fluoro-2-chloro-5-nitrobenzoyl chloride (VI) with diethyl ethoxymagnesium malonate to obtain diethyl (3-fluoro-2- Chloro-5-nitrobenzoyl) -malonate was obtained, and (f) diethyl (3-fluoro-2-chloro-5-nitrobenzoyl) -malonate was dissolved in the presence of sulfuric acid. Reacting with an acid to obtain 3-fluoro-2-chloro-5-nitroacetophenone (g), and (g) mercapto acetoic acid using the above-3-fluoro-2-chloro-5-nitroacetophenone To (2-acetyl-6-fluoro-4-nitrophenylthio) -acetic acid (h) and (h) said (2-acetyl-6-fluoro-4-nitrophenylthio) -acetic acid Preparation of 3-methyl-7-fluoro-5-nitrobenzothiophene (I) characterized by cyclization of (iii) to obtain 3-methyl-7 fluoro-5-nitrobenzothiophene (I). Way. 7-플루오로이사틴(Ⅲ)을 황산에 용해시키고, 질산으로 질화시키고 이 생성물을 산화제로 산화시킴을 특징으로 하는 3-플루오로-5-니트로안트라닐산(Ⅳ)의 제조방법.A process for preparing 3-fluoro-5-nitroanthranilic acid (IV) characterized by dissolving 7-fluoroisatin (III) in sulfuric acid, nitriding with nitric acid and oxidizing the product with an oxidizing agent. 3-플루오로-5-니트로안트라닐산(Ⅳ).3-Fluoro-5-nitroanthranilic acid (IV). 3-플루오로-5-니트로안트라닐산(Ⅳ)을 디아조화시키고, 이 디아조 생성물을 황산 제1구리 존재하에서 염산과 반응시킴을 특징으로 하는 3-플루오로-2-클로로-5-니트로벤조산(Ⅴ)의 제조방법.3-Fluoro-2-chloro-5-nitrobenzoic acid characterized by diazotizing 3-fluoro-5-nitroanthranilic acid (IV) and reacting this diazo product with hydrochloric acid in the presence of cuprous sulfate (V) The manufacturing method. 3-플루오로-2-클로로-5-니트로벤조산(Ⅴ).3-Fluoro-2-chloro-5-nitrobenzoic acid (V). 3-플루오로-2-클로로-5-니트로벤조산(Ⅴ)을 염화티오닐 또는 다른 적합한 염화물과 반응시킴을 특징으로 하는 3-플루오로-2-클로로-5-니트로벤조산 클로라이드 (Ⅵ)의 제조방법.Preparation of 3-fluoro-2-chloro-5-nitrobenzoic acid chloride (VI) characterized by reacting 3-fluoro-2-chloro-5-nitrobenzoic acid (V) with thionyl chloride or other suitable chloride Way. 3-플루오로-2-클로로-5-니트로벤조산 클로라이드.3-fluoro-2-chloro-5-nitrobenzoic acid chloride. 3-플루오로-2-플로로-5-니트로벤조산 클로라이드(Ⅵ)를 디에틸에톡시 마그네슘-말로네이트와 반응시킴을 특징으로 하는 디에틸(3-플루오로-2-클로로-5-니트로 벤조일)-말로네이트(Ⅶ)의 제조방법.Diethyl (3-fluoro-2-chloro-5-nitro benzoyl, characterized by reacting 3-fluoro-2-fluoro-5-nitrobenzoic acid chloride (VI) with diethylethoxy magnesium-malonate )-Method for producing malonate. 디에틸 (3-플루오로-2-클로로-5-니트로벤조일) 말로네이트(Ⅶ).Diethyl (3-fluoro-2-chloro-5-nitrobenzoyl) malonate (i). 디에틸 (3-플루오로-2-클로로-5-니트로벤조일) 말로네이트(Ⅶ)를 황산 존재하에 프로피온산과 반응시킴을 특징으로 하는 3-플루오로-2-클로로-5-니트로아세토페논(Ⅷ)의 제조방법.3-fluoro-2-chloro-5-nitroacetophenone characterized by reacting diethyl (3-fluoro-2-chloro-5-nitrobenzoyl) malonate with propionic acid in the presence of sulfuric acid Method of manufacture). 3-플루오로-2-클로로-5-니트로아세토페논(Ⅷ).3-fluoro-2-chloro-5-nitroacetophenone (iii). 3-플루오로-2-클로로-5-니트로아세토페논(Ⅷ)을 메크캅토아세트산과 반응시킴을 특징으로 하는 (2-아세틸-6-플루오로-4-니트로페닐티오) 아세트산(Ⅸ)의 제조방법.Preparation of (2-acetyl-6-fluoro-4-nitrophenylthio) acetic acid, characterized by reacting 3-fluoro-2-chloro-5-nitroacetophenone with meccaptoacetic acid Way. (2-아세틸-6-플루오로-4-니트로페닐티오) 아세트산(Ⅸ).(2-acetyl-6-fluoro-4-nitrophenylthio) acetic acid. (2-아세틸-6-플루오로-4-니트로페닐티오) 아세트산(Ⅸ)를 사이클화 시킴을 특징으로 하는 3-메틸-7-플루오로-5-니트로벤조오펜의 제조방법.(2-acetyl-6-fluoro-4-nitrophenylthio) A process for producing 3-methyl-7-fluoro-5-nitrobenzoofene characterized by cyclizing acetic acid. 일반식(Ⅹ)의 화합물.Compound of general formula (VII). 위 식 중에서, R1은 카르복실기이거나 임의로 치환된 카르보닐알킬기이고, R2는 할로겐, 아미노기 또는원오알킬 카르복실기이다.In the above formula, R 1 is a carboxyl group or an optionally substituted carbonylalkyl group, and R 2 is a halogen, amino group or a faroalkyl carboxyl group. ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.※ Note: The disclosure is based on the initial application.
KR1019850001166A 1984-02-27 1985-02-25 Method for preparing 3-methyl-7-fluoro-5-nitrobenzothiophene KR850006398A (en)

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DE19843406997 DE3406997A1 (en) 1984-02-27 1984-02-27 Process for the preparation of 3-methyl-7-fluoro-5-nitro- benzothiophene
DEP3406997.6 1984-02-27

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JPH06505255A (en) * 1991-02-14 1994-06-16 ブロカデス　ファルマ　ベスローテン　フェンノートシャップ Use of tetrahydro-thienopyridindole derivatives in the preparation of drugs for the treatment of dermatological diseases

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