KR960041167A - 임의의 2-치환 5-클로로이미다졸-4-카르보알데히드의 제조방법 - Google Patents
임의의 2-치환 5-클로로이미다졸-4-카르보알데히드의 제조방법 Download PDFInfo
- Publication number
- KR960041167A KR960041167A KR1019960016181A KR19960016181A KR960041167A KR 960041167 A KR960041167 A KR 960041167A KR 1019960016181 A KR1019960016181 A KR 1019960016181A KR 19960016181 A KR19960016181 A KR 19960016181A KR 960041167 A KR960041167 A KR 960041167A
- Authority
- KR
- South Korea
- Prior art keywords
- chloroimidazol
- substituted
- general formula
- ylidenemethyl
- dimethylamine
- Prior art date
Links
- -1 2-substituted 5-chloroimidazole-4-carbaldehyde Chemical class 0.000 title claims 5
- 238000000034 method Methods 0.000 claims abstract 4
- 150000001875 compounds Chemical class 0.000 claims abstract 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 2
- PBCVWYVRJHGIBO-UHFFFAOYSA-N 1-(2-butyl-5-chloroimidazol-4-ylidene)-n,n-dimethylmethanamine Chemical compound CCCCC1=NC(=CN(C)C)C(Cl)=N1 PBCVWYVRJHGIBO-UHFFFAOYSA-N 0.000 claims 2
- NJKMJBZGWGQJGN-UHFFFAOYSA-N 1-(5-chloro-2-propylimidazol-4-ylidene)-n,n-dimethylmethanamine Chemical compound CCCC1=NC(=CN(C)C)C(Cl)=N1 NJKMJBZGWGQJGN-UHFFFAOYSA-N 0.000 claims 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
- 150000001412 amines Chemical class 0.000 claims 2
- OHVWCRAXBOZMMG-UHFFFAOYSA-N 5-chloro-1h-imidazole-4-carbaldehyde Chemical compound ClC=1N=CNC=1C=O OHVWCRAXBOZMMG-UHFFFAOYSA-N 0.000 claims 1
- 125000003342 alkenyl group Chemical group 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 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
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- 125000005842 heteroatom Chemical group 0.000 claims 1
- 125000000623 heterocyclic group Chemical group 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 230000003301 hydrolyzing effect Effects 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- 239000001301 oxygen Substances 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- 150000003512 tertiary amines Chemical class 0.000 claims 1
- 229940030600 antihypertensive agent Drugs 0.000 abstract 1
- 239000002220 antihypertensive agent Substances 0.000 abstract 1
- 239000004009 herbicide Substances 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two 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
- C07D233/68—Halogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/96—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
하기 일반식 Ⅰ의 2-치환 5-클로로이미다졸-4-카르보알데히드의 신규 제조방법이 기재되어 있다.
상기 화합물은 혈압 강하제, 또는 제초제 제조 매우 중요한 출발물질이다.
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (9)
- 하기 일반식 Ⅱ의 임의의 2-치환 5-클로로이미다졸과 하기 일반식 Ⅲ의 아민과 반응시켜, 하기 일반식Ⅳ의 임의의 2-치환 5-클로로 이미다졸-4-일리덴메틸아민을 수득하고, 최종적으로 이 화합물을 가수분해하여, 목적 생성물을 수득하는 것을 특징으로 하는 하기 일반식 Ⅰ의 임의의 2-치환 5-클로로이미다졸-4-카르보알데히드의 제조방법.〔식중, R은 수소, 알킬기, 알케닐기, 시클로알킬기, 벤질기, 또는 페닐기를 나타내며, R1및 R2는 동일하거나 상이하며, (C1-C6)-알킬기를 나타내거나, 또는 R1및 R2가 함께 (C2-C3)-알킬렌 브리지를 형성하고, R3및 R4가 동일하거나 상이하며, (C1-C6)-알킬기를 나타내거나, 또는 R2및 R4는 아민 질소와 함께, 부가된 이종원자로 산소나 질소를 함유할 수 있는 5원, 또는 6원의 포화 복소환을 형성한다〕.
- 제1항에 있어서, 염기로서 3차 아민이 존재할 때에 반응이 수행됨을 특징으로 하는 제조방법.
- 제1항 또는 제2항에 있어서, 일반식 Ⅳ의 2-치환 5-클로로이미다졸-4-일리덴메틸아민이 단리되지 않음을 특징으로 하는 제조방법.
- 제1항 또는 제2항에 있어서, 일반식 Ⅲ의 아민과의 반응이, 불용성 용매의 존재하에, 온도가 20℃ 내지 200℃이 온도에서 수행되는 것을 특징으로 하는 제조방법.
- 하기 일반식 Ⅳ의 2-치환 5-클로로이미다졸-4-일리덴메틸아민〔식중, R, R3및 R4는 제1항에서 정의한 것과 동일하다〕.
- (2-n-부틸-5-클로로이미다졸-4-일리덴메틸)-디메틸아민.
- (2-n-부틸-5-클로로이미다졸-4-일리덴메틸)-디메틸아민.
- (2-n-프로필-5-클로로이미다졸-4-일리덴메틸)-디메틸아민.
- (2-n-프로필-5-클로로이미다졸-4-일리덴메틸)-디메틸아민.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH145195 | 1995-05-17 | ||
CH01451/95-3 | 1995-05-17 |
Publications (2)
Publication Number | Publication Date |
---|---|
KR960041167A true KR960041167A (ko) | 1996-12-19 |
KR100412248B1 KR100412248B1 (ko) | 2004-05-22 |
Family
ID=4210780
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
KR1019960016181A KR100412248B1 (ko) | 1995-05-17 | 1996-05-15 | 선택적으로2-치환된5-클로로이미다졸-4-카르브알데히드의제조방법 |
Country Status (10)
Country | Link |
---|---|
US (2) | US5698707A (ko) |
EP (1) | EP0743306B1 (ko) |
JP (1) | JP4140066B2 (ko) |
KR (1) | KR100412248B1 (ko) |
AT (1) | ATE198742T1 (ko) |
CA (1) | CA2175420C (ko) |
DE (1) | DE59606328D1 (ko) |
DK (1) | DK0743306T3 (ko) |
ES (1) | ES2155547T3 (ko) |
HU (1) | HU216154B (ko) |
Families Citing this family (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CA2175420C (en) * | 1995-05-17 | 2007-04-10 | Gareth Griffiths | Process for the preparation of optionally 2-substituted 5-chloroimidazole-4-carbaldehydes |
US6590106B2 (en) * | 1997-05-09 | 2003-07-08 | Pharm-Eco Laboratories, Inc. | Amino acid derivatives and methods of making the same |
WO2003006435A1 (en) * | 2001-07-09 | 2003-01-23 | Merck & Co., Inc. | Process for oxidation of alcohols |
US20040147787A1 (en) * | 2001-10-16 | 2004-07-29 | Miller Ross A | Process for oxidation of alcohols |
Family Cites Families (13)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
IL53783A (en) * | 1977-02-03 | 1982-08-31 | American Cyanamid Co | Imidazo(1,5-d)-as-triazine-4 (3h)-(thi)one derivatives,their preparation and pharmaceutical compositions containing them |
JPS5671074A (en) * | 1979-11-12 | 1981-06-13 | Takeda Chem Ind Ltd | 1,2-disubstituted-4-halogenoimidazole-5-acetic acid derivative |
US4345935A (en) * | 1981-10-05 | 1982-08-24 | Eli Lilly And Company | 2,4-Imidazolidinediones, compositions and herbicidal method |
RU2103262C1 (ru) * | 1992-07-16 | 1998-01-27 | Лонца АГ Гампель/Валлис | Способ получения 2-замещенных 5-хлоримидазол-4-карбальдегидов |
US5565577A (en) * | 1992-09-23 | 1996-10-15 | Smithkline Beecham Corporation | Process for preparing 1-alkyaryl-2-alkyl-5-formylimidazole |
US5484939A (en) * | 1993-03-12 | 1996-01-16 | Lonza Ltd. | 2-substituted 5-chlorimidazoles |
ATE157655T1 (de) * | 1993-03-12 | 1997-09-15 | Lonza Ag | Verfahren zur herstellung von gegebenfalls 2- substituierten 5-chlorimidazolen |
EP0614889A1 (de) * | 1993-03-12 | 1994-09-14 | Lonza Ag | Verfahren zur Herstellung von gegebenenfalls 2-substituierten 5-Chlorimidazol-4-carbaldehyden |
JP2517836B2 (ja) * | 1993-07-23 | 1996-07-24 | 株式会社コニカケミカル | 4−クロロイミダゾ―ル−5−カルバルデヒド誘導体の製造法 |
JPH08816B2 (ja) * | 1993-07-23 | 1996-01-10 | 株式会社コニカケミカル | 2−ブチル−4−クロロイミダゾール−5−カルバルデヒドの製造法 |
CA2135541C (en) * | 1993-11-15 | 2006-01-10 | Gareth Griffiths | Process for the preparation of 2-substituted 5-chloroimidazole-4-carbaldehydes |
US5395943A (en) * | 1994-02-16 | 1995-03-07 | Nippon Gohsei Kagaku Kogyo Kabushiki Kaisha | Method for purification of 2-alkyl-4-halo-5-formylimidazoles |
CA2175420C (en) * | 1995-05-17 | 2007-04-10 | Gareth Griffiths | Process for the preparation of optionally 2-substituted 5-chloroimidazole-4-carbaldehydes |
-
1996
- 1996-04-30 CA CA002175420A patent/CA2175420C/en not_active Expired - Fee Related
- 1996-05-09 JP JP11507196A patent/JP4140066B2/ja not_active Expired - Fee Related
- 1996-05-10 US US08/644,249 patent/US5698707A/en not_active Expired - Lifetime
- 1996-05-13 DE DE59606328T patent/DE59606328D1/de not_active Expired - Lifetime
- 1996-05-13 EP EP96107612A patent/EP0743306B1/de not_active Expired - Lifetime
- 1996-05-13 AT AT96107612T patent/ATE198742T1/de active
- 1996-05-13 DK DK96107612T patent/DK0743306T3/da active
- 1996-05-13 ES ES96107612T patent/ES2155547T3/es not_active Expired - Lifetime
- 1996-05-15 KR KR1019960016181A patent/KR100412248B1/ko not_active IP Right Cessation
- 1996-05-16 HU HUP9601325A patent/HU216154B/hu not_active IP Right Cessation
-
1997
- 1997-01-14 US US08/783,205 patent/US5684157A/en not_active Expired - Lifetime
Also Published As
Publication number | Publication date |
---|---|
CA2175420C (en) | 2007-04-10 |
HU9601325D0 (en) | 1996-07-29 |
HUP9601325A3 (en) | 1997-09-29 |
JPH08311037A (ja) | 1996-11-26 |
KR100412248B1 (ko) | 2004-05-22 |
EP0743306A1 (de) | 1996-11-20 |
EP0743306B1 (de) | 2001-01-17 |
JP4140066B2 (ja) | 2008-08-27 |
ATE198742T1 (de) | 2001-02-15 |
HU216154B (hu) | 1999-04-28 |
US5698707A (en) | 1997-12-16 |
DK0743306T3 (da) | 2001-02-05 |
ES2155547T3 (es) | 2001-05-16 |
CA2175420A1 (en) | 1996-11-18 |
DE59606328D1 (de) | 2001-02-22 |
US5684157A (en) | 1997-11-04 |
HUP9601325A2 (en) | 1997-04-28 |
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