KR840000538A - 2-(2-티에닐)-및 (3-티에닐)-에틸아민 유도체의 제조방법 - Google Patents
2-(2-티에닐)-및 (3-티에닐)-에틸아민 유도체의 제조방법 Download PDFInfo
- Publication number
- KR840000538A KR840000538A KR1019820002914A KR820002914A KR840000538A KR 840000538 A KR840000538 A KR 840000538A KR 1019820002914 A KR1019820002914 A KR 1019820002914A KR 820002914 A KR820002914 A KR 820002914A KR 840000538 A KR840000538 A KR 840000538A
- Authority
- KR
- South Korea
- Prior art keywords
- compound
- derivative
- general formula
- formula
- thienyl
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title claims 6
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 title claims 2
- DTDHODSOKFHWQE-UHFFFAOYSA-N n-ethylthiophen-3-amine Chemical class CCNC=1C=CSC=1 DTDHODSOKFHWQE-UHFFFAOYSA-N 0.000 title claims 2
- -1 nitro, cyano, amino, carboxy Chemical group 0.000 claims 7
- 125000000217 alkyl group Chemical group 0.000 claims 6
- 150000001875 compounds Chemical class 0.000 claims 6
- 238000000034 method Methods 0.000 claims 6
- 125000003545 alkoxy group Chemical group 0.000 claims 4
- 238000006243 chemical reaction Methods 0.000 claims 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 3
- 125000006615 aromatic heterocyclic group Chemical class 0.000 claims 3
- 125000001475 halogen functional group Chemical group 0.000 claims 3
- 125000000623 heterocyclic group Chemical class 0.000 claims 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims 2
- 125000005843 halogen group Chemical group 0.000 claims 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 2
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 claims 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims 1
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 150000001298 alcohols Chemical class 0.000 claims 1
- 239000003513 alkali Substances 0.000 claims 1
- 229910052783 alkali metal Inorganic materials 0.000 claims 1
- 150000001342 alkaline earth metals Chemical class 0.000 claims 1
- 150000001408 amides Chemical class 0.000 claims 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims 1
- 239000002585 base Substances 0.000 claims 1
- 229910010277 boron hydride Inorganic materials 0.000 claims 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
- 239000003638 chemical reducing agent Substances 0.000 claims 1
- 150000004292 cyclic ethers Chemical class 0.000 claims 1
- 125000004663 dialkyl amino group Chemical group 0.000 claims 1
- 125000002425 furfuryl group Chemical group C(C1=CC=CO1)* 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 238000010438 heat treatment Methods 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- OBTSLRFPKIKXSZ-UHFFFAOYSA-N lithium potassium Chemical compound [Li].[K] OBTSLRFPKIKXSZ-UHFFFAOYSA-N 0.000 claims 1
- 229910052749 magnesium Inorganic materials 0.000 claims 1
- 239000011777 magnesium Substances 0.000 claims 1
- 150000002681 magnesium compounds Chemical class 0.000 claims 1
- 229910052751 metal Inorganic materials 0.000 claims 1
- 239000002184 metal Substances 0.000 claims 1
- 125000001624 naphthyl group Chemical group 0.000 claims 1
- 239000003960 organic solvent Substances 0.000 claims 1
- 229910052700 potassium Inorganic materials 0.000 claims 1
- 239000011591 potassium Substances 0.000 claims 1
- 125000004076 pyridyl group Chemical group 0.000 claims 1
- 229910052708 sodium Inorganic materials 0.000 claims 1
- 239000011734 sodium Substances 0.000 claims 1
- 229910000033 sodium borohydride Inorganic materials 0.000 claims 1
- 239000012279 sodium borohydride Substances 0.000 claims 1
- 150000003388 sodium compounds Chemical class 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- 150000003462 sulfoxides Chemical class 0.000 claims 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 1
- 125000001544 thienyl group Chemical group 0.000 claims 1
- 239000008096 xylene Substances 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having sulfur atoms, with or without selenium or tellurium atoms, as the only ring hetero atoms
- C07F9/655345—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having sulfur atoms, with or without selenium or tellurium atoms, as the only ring hetero atoms the sulfur atom being part of a five-membered ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/14—Radicals substituted by singly bound hetero atoms other than halogen
- C07D333/20—Radicals substituted by singly bound hetero atoms other than halogen by nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/40—Esters thereof
- C07F9/4003—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4006—Esters of acyclic acids which can have further substituents on alkyl
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Compositions Of Oxide Ceramics (AREA)
- Saccharide Compounds (AREA)
- Liquid Deposition Of Substances Of Which Semiconductor Devices Are Composed (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Vehicle Body Suspensions (AREA)
- Electrical Control Of Air Or Fuel Supplied To Internal-Combustion Engine (AREA)
- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Abstract
내용 없음
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (26)
- 일반식(Ⅰ)으로 표시되는 2-(2-티에닐)-및 (3-티에닐)-에틸아민의 제조방법에 있어서, 상기식
-
- 에서 R1(2-, 3-, 4- 또는 5-위치에서)온 수소원자, 직쇄 또는 분지쇄 알킬기와, 알킬, 페닐, 할로, 니트로, 시아노, 아미노, 카르복시 또는 알콕시기에 의하여 임의로 모노-또는 폴리-치환된 복소환식 또는 비복소환식 방향족기를 나타내고 ; R1은 알콕시기, 할로겐원자, 니트로, 카르복실, 시아노, 아미노기를 나타내며, 티오펜핵의 2 또는 3위치에 연결된 아미노에틸에서 R2는 수소원자 또는 직쇄 또는 분지쇄 알킬기와, 알킬, 페닐, 할로, 니트로, 시아노, 아미노, 카르복시 또는 알콕시기에 의하여 임의로 모노-또는 -폴리-치환된 복소환식 또는 비-복소환식 방향족기를 나타낸다 ; Ar은 알킬, 페닐, 할로, 니트로, 시아노, 아미노 또는 카르복시기에 의하여 임의로 모노-또는 폴리-치환된 복소환식 또는 비-복소환식 방향족기를 나타낸다).
- -다음 일반식(Ⅴ)의 카르바이온 :
-
- 을 가열하에 다음 일반식(Ⅵ) :
-
- 로 변환시킨 후, 물에 포집하여 다음 일반식(Ⅶ)의 화합물을 제조하고 :
-
- -화합물(Ⅶ)을 환원제의 작용하에 다음 일반식(Ⅷ)의 유도체로 변환시키고 ;
-
- -화합물(Ⅷ)을 먼저 일반식 B'-M' 의 염기와 반응시킨 다음 일반식(Ⅸ)의 할로겐화 유도체 :
- AR-CHX-R2(Ⅸ)
- (상상기식에서 Ar과 R2는 전술한 바와 같고 X는 할로겐을 나타낸다)와 반응시켜서 다음 일반식(X)의 유도체를 제조하고 ;
-
- -화합물(X)을 산의 작용하에 일반식(Ⅰ)의 화합물로 변환시켜서 제조함을 특징으로 상기 화합물(Ⅰ)의 제조방법.
- 청구범위 1에 있어서, Ar이 티에닐, 푸르푸릴, 피리딜, 페닐 또는 나프틸기임을 특징으로 하는 상기 제조방법.
- 청구범위 1에 있어서, M또는 M'가 알카리 또는 알카리토류 금속이고, B또는 B'를 수소, 히드록시, 아미노, 모노-또는 디알킬아미노, 직쇄 또는 분지쇄 알킬 또는 직쇄나 알콕시에 상응하는 음전하기로부터 선택하거나 염기 BM또는 B'M'가 유기마그네슘 화합물 또는 유기나트륨 화합물임을 특징으로 하는 상기 제조방법.
- 청구범위 3에 있어서, M또는 M'를 나트륨, 리튬 칼륨과 마그네슘으로부터 선택한 금속임을 특징으로 상기 제조방법.
- 청구범위 1에 있어서, 염기 BM를 화학량론적 양으로 사용할 때, 일반식(Ⅵ)의 유도체를 일반식의 (Ⅸ) 할로 겐화 유도체와 반응시킨 다음 환원시켜서 함을 특징으로 하는 상기 제조방법.
- 청구범위 1에 있어서, 유도체(Ⅴ)을 유도체(Ⅵ)로 변환시키기 위한 반응을 -78~+150℃의 온도에서 행함을 특징으로 하는 상기 제조방법.
- 청구범위 3에 있어서, 높은 범위 온도내에서, 염기의 성질에 따라 선택한 온도에서 반응을 행함을 특징으로 하는 상기 제조방법.
- 청구범위 6 또는 7에 있어서, 직쇄 및 환식 에테르, 방향족 탄화수소, 알콜, 아미드와 설폭사이드와 같은 유기용매에서 반응을 행함을 특징으로 하는 상기 제조방법.
- 청구범위 8에 있어서, 용매를 테트라하이드로푸란, 벤젠, 톨루엔, 크실렌, 에타놀, 디메틸포름 아미드와 디메틸설폭 사이드로부터 선택함을 특징으로 하기 상기 제조방법.
- 일반식(Ⅶ)의 유도체의 환원을 알칼리 금속 붕소 수소화물, 대표적으로 수소화붕소 나트륨, 또는 수소 화붕소 칼륨으로 행함을 특징으로 하는 상기 제조방법.
- ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8113064A FR2508455A1 (fr) | 1981-06-30 | 1981-06-30 | Procede de preparation de derives des (thienyl-2)- et (thienyl-3)-2 ethylamines |
| FR8113064 | 1981-06-30 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR840000538A true KR840000538A (ko) | 1984-02-25 |
Family
ID=9260131
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019820002914A KR840000538A (ko) | 1981-06-30 | 1982-06-30 | 2-(2-티에닐)-및 (3-티에닐)-에틸아민 유도체의 제조방법 |
Country Status (24)
| Country | Link |
|---|---|
| US (1) | US4458086A (ko) |
| EP (1) | EP0068983B1 (ko) |
| JP (1) | JPS5813583A (ko) |
| KR (1) | KR840000538A (ko) |
| AT (1) | ATE18764T1 (ko) |
| AU (1) | AU549063B2 (ko) |
| CA (1) | CA1205808A (ko) |
| CS (1) | CS244112B2 (ko) |
| DD (1) | DD202712A5 (ko) |
| DE (1) | DE3270081D1 (ko) |
| DK (1) | DK289482A (ko) |
| ES (1) | ES514191A0 (ko) |
| FI (1) | FI822317L (ko) |
| FR (1) | FR2508455A1 (ko) |
| GR (1) | GR77205B (ko) |
| HU (1) | HU194861B (ko) |
| IE (1) | IE53242B1 (ko) |
| IL (1) | IL65982A (ko) |
| NO (1) | NO155344C (ko) |
| NZ (1) | NZ200854A (ko) |
| PT (1) | PT75154B (ko) |
| SU (1) | SU1181543A3 (ko) |
| YU (1) | YU142882A (ko) |
| ZA (1) | ZA824616B (ko) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6145A (ja) * | 1984-06-09 | 1986-01-06 | Kaken Pharmaceut Co Ltd | Ｎ‐（４‐ｔｅｒｔ‐ブチルベンジル）‐Ｎ‐メチル‐１‐ナフチルメチルアミンおよびそれを有効成分とする抗真菌剤 |
| US5334628A (en) * | 1984-06-09 | 1994-08-02 | Kaken Pharmaceutical Co., Ltd. | Amine derivatives, processes for preparing the same and fungicides containing the same |
| EP0253594A3 (en) * | 1986-07-16 | 1989-10-11 | COOKSON GROUP plc | Polymerisable thiophene monomers, their production and polymers prepared therefrom |
| FR2624860B1 (fr) * | 1987-12-18 | 1990-06-01 | Sanofi Sa | Procede de preparation de la n-(chloro-2 benzyl) (thienyl-2)-2 ethylamine |
| US4900539A (en) * | 1988-12-22 | 1990-02-13 | The United States Of America As Represented By The United States Department Of Energy | Radiohalogenated thienylethylamine derivatives for evaluating local cerebral blood flow |
| US7820180B2 (en) * | 2004-09-24 | 2010-10-26 | The Trustees Of The University Of Pennsylvania | Listeria-based and LLO-based vaccines |
| HU225504B1 (en) * | 1997-05-13 | 2007-01-29 | Sanofi Aventis | Novel halophenyl-(2-(2-thienyl)-ethylamino)-acetonitriles and process for producing them |
-
1981
- 1981-06-30 FR FR8113064A patent/FR2508455A1/fr active Granted
-
1982
- 1982-06-01 IE IE1312/82A patent/IE53242B1/en unknown
- 1982-06-04 NZ NZ200854A patent/NZ200854A/xx unknown
- 1982-06-06 IL IL65982A patent/IL65982A/xx unknown
- 1982-06-09 GR GR68376A patent/GR77205B/el unknown
- 1982-06-10 AU AU84756/82A patent/AU549063B2/en not_active Ceased
- 1982-06-14 ES ES514191A patent/ES514191A0/es active Granted
- 1982-06-17 EP EP82401101A patent/EP0068983B1/fr not_active Expired
- 1982-06-17 DE DE8282401101T patent/DE3270081D1/de not_active Expired
- 1982-06-17 AT AT82401101T patent/ATE18764T1/de not_active IP Right Cessation
- 1982-06-25 SU SU823456110A patent/SU1181543A3/ru active
- 1982-06-28 DK DK289482A patent/DK289482A/da not_active Application Discontinuation
- 1982-06-29 ZA ZA824616A patent/ZA824616B/xx unknown
- 1982-06-29 NO NO822226A patent/NO155344C/no unknown
- 1982-06-29 CA CA000406266A patent/CA1205808A/en not_active Expired
- 1982-06-29 CS CS824897A patent/CS244112B2/cs unknown
- 1982-06-29 HU HU822108A patent/HU194861B/hu unknown
- 1982-06-29 DD DD82241199A patent/DD202712A5/de unknown
- 1982-06-29 US US06/393,388 patent/US4458086A/en not_active Expired - Fee Related
- 1982-06-29 FI FI822317A patent/FI822317L/fi not_active Application Discontinuation
- 1982-06-29 PT PT75154A patent/PT75154B/pt not_active IP Right Cessation
- 1982-06-30 YU YU01428/82A patent/YU142882A/xx unknown
- 1982-06-30 JP JP57113844A patent/JPS5813583A/ja active Pending
- 1982-06-30 KR KR1019820002914A patent/KR840000538A/ko unknown
Also Published As
| Publication number | Publication date |
|---|---|
| ES8305347A1 (es) | 1983-04-01 |
| PT75154B (fr) | 1984-05-29 |
| CA1205808A (en) | 1986-06-10 |
| EP0068983A1 (fr) | 1983-01-05 |
| NZ200854A (en) | 1985-09-13 |
| IL65982A (en) | 1985-09-29 |
| DD202712A5 (de) | 1983-09-28 |
| FR2508455A1 (fr) | 1982-12-31 |
| AU8475682A (en) | 1983-01-06 |
| CS489782A2 (en) | 1985-08-15 |
| CS244112B2 (en) | 1986-07-17 |
| ES514191A0 (es) | 1983-04-01 |
| DK289482A (da) | 1982-12-31 |
| IE53242B1 (en) | 1988-09-14 |
| US4458086A (en) | 1984-07-03 |
| YU142882A (en) | 1984-12-31 |
| EP0068983B1 (fr) | 1986-03-26 |
| IE821312L (en) | 1982-12-30 |
| NO155344B (no) | 1986-12-08 |
| SU1181543A3 (ru) | 1985-09-23 |
| ZA824616B (en) | 1983-04-27 |
| PT75154A (fr) | 1982-07-01 |
| HU194861B (en) | 1988-03-28 |
| JPS5813583A (ja) | 1983-01-26 |
| FI822317L (fi) | 1982-12-31 |
| FR2508455B1 (ko) | 1984-01-06 |
| DE3270081D1 (en) | 1986-04-30 |
| ATE18764T1 (de) | 1986-04-15 |
| FI822317A0 (fi) | 1982-06-29 |
| GR77205B (ko) | 1984-09-11 |
| NO822226L (no) | 1983-01-03 |
| IL65982A0 (en) | 1982-09-30 |
| AU549063B2 (en) | 1986-01-09 |
| NO155344C (no) | 1987-03-18 |
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