KR890009879A - 5- 아미노-1- 페닐-4-니트로피라졸의 제조방법 - Google Patents
5- 아미노-1- 페닐-4-니트로피라졸의 제조방법 Download PDFInfo
- Publication number
- KR890009879A KR890009879A KR1019880016753A KR880016753A KR890009879A KR 890009879 A KR890009879 A KR 890009879A KR 1019880016753 A KR1019880016753 A KR 1019880016753A KR 880016753 A KR880016753 A KR 880016753A KR 890009879 A KR890009879 A KR 890009879A
- Authority
- KR
- South Korea
- Prior art keywords
- optionally
- formula
- process according
- optionally substituted
- moles
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims 8
- NTFNTWUWQVTINQ-UHFFFAOYSA-N 4-nitro-2-phenylpyrazol-3-amine Chemical compound NC1=C([N+]([O-])=O)C=NN1C1=CC=CC=C1 NTFNTWUWQVTINQ-UHFFFAOYSA-N 0.000 title claims 2
- -1 cyano, nitro, methyl Chemical group 0.000 claims 9
- 239000002253 acid Substances 0.000 claims 5
- 239000002585 base Substances 0.000 claims 4
- KXHWGIRKJGALAI-UHFFFAOYSA-N 3-chloro-4-nitro-1,2-thiazole Chemical compound [O-][N+](=O)C1=CSN=C1Cl KXHWGIRKJGALAI-UHFFFAOYSA-N 0.000 claims 2
- 125000001931 aliphatic group Chemical group 0.000 claims 2
- 229910052783 alkali metal Inorganic materials 0.000 claims 2
- 125000000217 alkyl group Chemical group 0.000 claims 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims 2
- 125000005842 heteroatom Chemical group 0.000 claims 2
- 125000000623 heterocyclic group Chemical group 0.000 claims 2
- 239000001257 hydrogen Substances 0.000 claims 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 2
- 229910052757 nitrogen Inorganic materials 0.000 claims 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- 125000001424 substituent group Chemical group 0.000 claims 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 1
- 239000002841 Lewis acid Substances 0.000 claims 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims 1
- MOVRNJGDXREIBM-UHFFFAOYSA-N aid-1 Chemical compound O=C1NC(=O)C(C)=CN1C1OC(COP(O)(=O)OC2C(OC(C2)N2C3=C(C(NC(N)=N3)=O)N=C2)COP(O)(=O)OC2C(OC(C2)N2C3=C(C(NC(N)=N3)=O)N=C2)COP(O)(=O)OC2C(OC(C2)N2C3=C(C(NC(N)=N3)=O)N=C2)COP(O)(=O)OC2C(OC(C2)N2C(NC(=O)C(C)=C2)=O)COP(O)(=O)OC2C(OC(C2)N2C3=C(C(NC(N)=N3)=O)N=C2)COP(O)(=O)OC2C(OC(C2)N2C3=C(C(NC(N)=N3)=O)N=C2)COP(O)(=O)OC2C(OC(C2)N2C3=C(C(NC(N)=N3)=O)N=C2)COP(O)(=O)OC2C(OC(C2)N2C(NC(=O)C(C)=C2)=O)COP(O)(=O)OC2C(OC(C2)N2C3=C(C(NC(N)=N3)=O)N=C2)COP(O)(=O)OC2C(OC(C2)N2C3=C(C(NC(N)=N3)=O)N=C2)COP(O)(=O)OC2C(OC(C2)N2C3=C(C(NC(N)=N3)=O)N=C2)COP(O)(=O)OC2C(OC(C2)N2C(NC(=O)C(C)=C2)=O)COP(O)(=O)OC2C(OC(C2)N2C3=C(C(NC(N)=N3)=O)N=C2)COP(O)(=O)OC2C(OC(C2)N2C3=C(C(NC(N)=N3)=O)N=C2)COP(O)(=O)OC2C(OC(C2)N2C3=C(C(NC(N)=N3)=O)N=C2)CO)C(O)C1 MOVRNJGDXREIBM-UHFFFAOYSA-N 0.000 claims 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 claims 1
- 150000008041 alkali metal carbonates Chemical class 0.000 claims 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 claims 1
- 150000001412 amines Chemical class 0.000 claims 1
- 125000003710 aryl alkyl group Chemical group 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 1
- 229910052794 bromium Inorganic materials 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 239000000460 chlorine Substances 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 claims 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 229910052731 fluorine Inorganic materials 0.000 claims 1
- 239000011737 fluorine Substances 0.000 claims 1
- 125000001072 heteroaryl group Chemical group 0.000 claims 1
- 150000002500 ions Chemical class 0.000 claims 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 150000007517 lewis acids Chemical class 0.000 claims 1
- 150000007522 mineralic acids Chemical class 0.000 claims 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- 150000003512 tertiary amines Chemical class 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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 ring carbon atoms
- C07D231/16—Halogen atoms or nitro radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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 ring carbon atoms
- C07D231/38—Nitrogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
내용 없음
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (9)
- 일반식(Ⅱ)의 아릴히드라진을, 경우에 따라 보조염기의 존재하, 경우에 따라 희석제의 존재하 및 경우에 따라 반응 보조제의 존재하에, 구조식(Ⅲ)의 3-클로로-4-니트로-이소티아졸과 반응시킴을 특징으로 하며, 일반식(Ⅰ)의 5-아미노-1-페닐-4-니트로피라졸을 제조하는 방법.상기식에서, Ar은 임의 치환된 페닐이다.
- 제1항에 있어서, 반응을 -30내지 +150oC의 온도에서 수행함을 특징으로 하는 방법.
- 제1항에 있어서, 일반식(Ⅱ)의 아릴히드라진 몰당 3-클로로-4-니트로-이소티아졸 1 내지 1.5몰, 및 경우에 따라 보조염기 1 내지 10몰 및 경우에 따라 산 반응 보조제 1 내지 10몰을 사용함을 특징으로 하는 방법.
- 제1항에 있어서, 일반식(Ⅱ)의 아릴히드라진 몰당 3-클로로-4-니트로-이소티아졸 1 내지 1.3몰, 및 경우에 따라 보조염기 1 내지 5몰 및 경우에 따라 산 반응 보조제 1 내지 10몰을 사용함을 특징으로 하는 방법.
- 제1항에 있어서, 일반식(Ⅳ)의 아민을 보조 염기로서 사용하는 방법.상기식에서, R1및 R2는 각각 독립적으로 수소, 알킬, 사이클로알킬 또는 각 경우에 임의 치환된 아르알킬, 아릴 또는 헤테로아릴이거나, 이들이 결합되어 있는 질소원자와 함께 임의 치환된 헤테로사이클릭 환(이는 경우에 따라 추가의 헤테로원자를 함유할 수 있다)이다.
- 제5항에 있어서, 일반식(Ⅳ)에서 R1및 R2가 각각 독릭적으로 수소, 탄소수 1 내지 4의 직쇄 또는 측쇄 알킬, 탄소수 3 내지 7의 사이클로알킬, 또는 각각 동일하거나 상이한 치환체(여기에서, 적합한 치환체는 불소, 염소, 브롬, 시아노, 니트로, 메틸, 에틸, n-또는 i-프로필, n-, i-, s- 또는 t-부틸, 메톡시, 에톡시, n- 또는 i-프로폭시, 메틸티오, 트리플루오로메틸, 트리폴루오로메톡시, 트리플루오로메틸티오, 메톡시, 카보닐 또는 에톡시카보닐이다)에 의해 임으로 일차환, 이치환 또는 삼치환된 페닐 또는 벤질이거나, R1및 R2가 이들이 결합되어 있는 질소원자와 함께 5원 또는 6원 포화 헤테로사이클릭 환(이는 경우에 따라 1 내지 3개의 동일하거나 상이한 헤테로원자를 추가로 함유할 수 있다)임을 특징으로 하는 방법.
- 제1항에 있어서, 반응을 산 반응 보조제의 존재하에 수행함을 특징으로 하는 방법.
- 제7항에 있어서, 산 반응 보조제로서, 무기산, 지방족 또는 방향족 카복실산, 지방족 또는 방향족 설폰산, 루이스산 또는 산 이온 교환제를 사용함을 특징으로 하는 방법.
- 제1항에 있어서, 염기로서 알칼리 금속 하이드록 사이드, 알칼리 토금속 하이드록사이드, 알칼리 금속카보네이트, 알칼리 금속 하이드로겐 카보네이트, 알칼리 금속 아세테이트 또는 3급 아민의 존재하에 반응을 수행함을 특징으로 하는 방법.※참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19873742819 DE3742819A1 (de) | 1987-12-17 | 1987-12-17 | Verfahren zur herstellung von 5-amino-1-phenyl-4-nitro-pyrazolen |
| DEP3742819.5 | 1987-12-17 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR890009879A true KR890009879A (ko) | 1989-08-04 |
Family
ID=6342842
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019880016753A KR890009879A (ko) | 1987-12-17 | 1988-12-16 | 5- 아미노-1- 페닐-4-니트로피라졸의 제조방법 |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US4892958A (ko) |
| EP (1) | EP0320764A3 (ko) |
| JP (1) | JPH01197472A (ko) |
| KR (1) | KR890009879A (ko) |
| DE (1) | DE3742819A1 (ko) |
| HU (1) | HU201310B (ko) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2746310B1 (fr) | 1996-03-22 | 1998-06-12 | Oreal | Compositions de teinture des fibres keratiniques contenant des pyrazolin-3,5-dione ; leur utilisation pour la teinture comme coupleurs, procede de teinture |
| FR2746307B1 (fr) | 1996-03-22 | 1998-04-30 | Oreal | Compositions de teinture des fibres keratiniques contenant des pyrrolo-azoles ; utilisation comme coupleurs ; procede de teinture |
| FR2746306B1 (fr) | 1996-03-22 | 1998-04-30 | Oreal | Compositions de teinture des fibres keratiniques contenant des pyrazolo-azoles ; leur utilisation pour la teinture comme coupleurs, procede de teinture |
| FR2746309B1 (fr) | 1996-03-22 | 1998-04-17 | Oreal | Composition de teinture des fibres keratiniques contenant des pyrazolopyrimidineoxo ; leur utilisation pour la teinture comme coupleurs, procedes de teinture |
| FR2746391B1 (fr) | 1996-03-22 | 1998-04-17 | Oreal | Compositions cosmetiques a base de pyrazolin-4,5-diones, nouvelles pyrazolin-4,5 diones, procedes de preparation et utilisations |
| FR2746308B1 (fr) * | 1996-03-22 | 1998-04-30 | Oreal | Compositions de teinture des fibres keratiniques contenant des imidazolo-azoles ; leur utilisation en teinture comme coupleurs ; procede de teinture |
| US7934594B2 (en) * | 2008-02-22 | 2011-05-03 | Henderson Products, Inc. | Conveyor system for vehicle |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3285930A (en) * | 1964-11-18 | 1966-11-15 | Phillips Petroleum Co | Isothiazoles |
| DE3402308A1 (de) * | 1984-01-24 | 1985-08-01 | Bayer Ag, 5090 Leverkusen | Herbizide mittel auf basis von pyrazolderivaten |
| DE3528478A1 (de) * | 1985-08-08 | 1987-02-12 | Bayer Ag | 1-aryl-5-hydrazino-pyrazole |
| DE3617977A1 (de) * | 1985-12-05 | 1987-06-11 | Bayer Ag | 5-dichloracetamido-4-nitro-1-aryl-pyrazole |
-
1987
- 1987-12-17 DE DE19873742819 patent/DE3742819A1/de active Pending
-
1988
- 1988-12-07 EP EP88120406A patent/EP0320764A3/de not_active Ceased
- 1988-12-08 US US07/282,225 patent/US4892958A/en not_active Expired - Fee Related
- 1988-12-16 HU HU886474A patent/HU201310B/hu not_active IP Right Cessation
- 1988-12-16 KR KR1019880016753A patent/KR890009879A/ko not_active Application Discontinuation
- 1988-12-16 JP JP63316550A patent/JPH01197472A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| HUT49854A (en) | 1989-11-28 |
| DE3742819A1 (de) | 1989-07-13 |
| HU201310B (en) | 1990-10-28 |
| JPH01197472A (ja) | 1989-08-09 |
| US4892958A (en) | 1990-01-09 |
| EP0320764A2 (de) | 1989-06-21 |
| EP0320764A3 (de) | 1990-04-04 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| KR850001171A (ko) | 퀴놀린 화합물의 제조방법 | |
| DK0606024T3 (da) | Erythromycinderivater, en fremgangsmåde til deres fremstilling samt deres anvendelse som lægemidler | |
| KR860000272A (ko) | 헤테로아릴옥시아세트아미드의 제조방법 | |
| KR840000508A (ko) | 4-아닐리노피리미딘 유도체의 제조방법 | |
| DK402280A (da) | Fremgangsmaade til fremstilling af diphenulethere | |
| KR890009879A (ko) | 5- 아미노-1- 페닐-4-니트로피라졸의 제조방법 | |
| KR850005426A (ko) | 5-할로겐오알킬-1,3,4-티아디아졸-2-일옥시아세트아미드의 제조방법 | |
| KR900003156A (ko) | 진통제 화합물, 그의 제조방법 및 그를 함유하는 약학 조성물 | |
| KR850005449A (ko) | 메틸렌디포스폰산 유도체의 제조방법 | |
| EA200000484A1 (ru) | Способ получения производных тиазолидиндиона | |
| KR890011904A (ko) | 안드로스타-1,4, -디엔-3,17-디온의 6-메틸렌 유도체 합성방법 | |
| EA200000065A1 (ru) | Способ селективного получения z-изомера 3-(2-замещенный-винил) цефалоспорина | |
| US3265706A (en) | Processes for preparing certain 2-substituted benzimidazole compounds | |
| DK466786A (da) | Fremgangsmaade til fremstilling af n-substituerede dihydrolysergsyre-derivater | |
| GB1527807A (en) | Thiazolines | |
| KR860003231A (ko) | 2-시아노벤즈 이미다졸 유도체의 제조방법 | |
| DK0968189T3 (da) | Fremgangsmåde til fremstilling af nicotinsyrer | |
| KR840005449A (ko) | 벤조티오 피라노 피리디논 | |
| KR840001974A (ko) | 1-[3-(6-플루오로-1,2-벤즈이속사졸-3-일)프로필]-4-(치환된)-피페라진 및-피레리딘의 제조방법 | |
| KR830003460A (ko) | 면역조절 활성을 갖는 치환된 피페라진 및 피페리딘 | |
| GB1412546A (en) | Morpholine derivatives | |
| KR850007245A (ko) | 2-(알콕스이미노알콕시카보닐)-페닐설포닐우레아의 제조방법 | |
| KR870010006A (ko) | 1-아릴-5-아미노-피라졸의 제조방법 | |
| KR860002474A (ko) | 치환된 페닐술포닐아졸의 제조방법 | |
| KR920012048A (ko) | 퀴녹살리닐옥시페녹시프로피온산의 광학적 활성 에스테르의 제조방법 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| WITN | Application deemed withdrawn, e.g. because no request for examination was filed or no examination fee was paid |