KR800000385B1 - 이속사졸 유도체의 제조법 - Google Patents
이속사졸 유도체의 제조법 Download PDFInfo
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- KR800000385B1 KR800000385B1 KR1019800000199A KR740000199A KR800000385B1 KR 800000385 B1 KR800000385 B1 KR 800000385B1 KR 1019800000199 A KR1019800000199 A KR 1019800000199A KR 740000199 A KR740000199 A KR 740000199A KR 800000385 B1 KR800000385 B1 KR 800000385B1
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- 150000002545 isoxazoles Chemical class 0.000 title description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 14
- 125000003118 aryl group Chemical group 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 9
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 6
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 claims description 5
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000002947 alkylene group Chemical group 0.000 claims description 3
- 125000000304 alkynyl group Chemical group 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- SVUXRMADZWVVCT-UHFFFAOYSA-N 3-isocyanato-1,2-oxazole Chemical compound O=C=NC=1C=CON=1 SVUXRMADZWVVCT-UHFFFAOYSA-N 0.000 claims description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 239000011593 sulfur Substances 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- AFUIIDSTZFNDHA-UHFFFAOYSA-N 1,2-oxazol-3-ylcarbamothioic S-acid Chemical compound SC(=O)NC=1C=CON=1 AFUIIDSTZFNDHA-UHFFFAOYSA-N 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- -1 butadienyl Chemical group 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 150000001540 azides Chemical class 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 150000002431 hydrogen Chemical group 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- IQMVRIMSTBTDLV-UHFFFAOYSA-N 5-tert-butyl-3-isocyanato-1,2-oxazole Chemical compound CC(C)(C)C1=CC(N=C=O)=NO1 IQMVRIMSTBTDLV-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 241000195493 Cryptophyta Species 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000004414 alkyl thio group Chemical group 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- XLJMAIOERFSOGZ-UHFFFAOYSA-N anhydrous cyanic acid Natural products OC#N XLJMAIOERFSOGZ-UHFFFAOYSA-N 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000004369 butenyl group Chemical group C(=CCC)* 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000000480 butynyl group Chemical group [*]C#CC([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000012295 chemical reaction liquid Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
- 230000002363 herbicidal effect Effects 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 1
- 125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000013077 target material Substances 0.000 description 1
- 239000013076 target substance Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 125000005425 toluyl group Chemical group 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
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- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Abstract
내용 없음.
Description
본 발명은 다음 일단식(I)의 이속사졸 유도체의 제조법에 관한 것이다.
상기 식에서,
R은 수소, 단소수 2이상의 알킬기 또는 아릴기를 나타내고,
R2는 알킬기, 알케닐기, 알키닐기, 아르알킬기 또는 아릴기를 나타내고,
X는 수소, 알킬기 또는 할로겐를 나타내머,
Y는 산소 또는 황을 나타내고,
R과 X는 연결하여 알킬렌기를 형성해도 좋다.
상기 알킬기, 아르알킬기 및 아릴기는 할로겐, 알킬기, 알콕시기 및 히드록시기로부터 선택된 1이상의치 환기를 가져도 좋다.
상기 이속사졸 유도체(I)는 다음 방법에 의해서 제조된다.
상기 식에서,
R, R2, X 및 Y는 전술한 바와 같다.
상기 정의에 대해서 더욱 용어를 보충 설명하면, 알킬기로서는 메틸, 에틸, 프로필, i-프로필, t-부틸, 시클로프로필, 시클로헥실 등이, 아릴기로서는 페닐, 나프틸 등이, 알케닐기로서는 비닐, 아릴, 부테닐, 부타디에닐, 시콜로헥세닐 등이, 알키닐기로서는 에티닐, 프로페닐, 부티닐 등이, 아르알킬기로서는 벤질, 펜에틸 등이, 알킬렌기로서는 테트라메틸렌, 펜타메밀렌 등이, 알콕시기로서는 메톡시, 에톡시, 프로폭시등이, 알킬티오기로서는 메밀티오, 에틸티오, 프로필티오 등이, 아실기로서는 포르밀, 아세틸, 프로피오닐, 부티릴, 아크릴로일, 메타크밀로일, 크로로노일, 벤조일, 톨루오일, 신나모일, 프로일, 데노일 등이, 할로겐으로서는 염소, 브롬, 요드 등이 각각 예시되지만, 본 발명의 목적상 이들에 한정되는 것은 아니다.또 이들의 알킬기, 아르알킬기 및 아릴기는 할로겐, 알킬기, 알콕시기 및 하이드록시기로부터 선택된 1이상의 치환기를 가져도 좋다.
본 발명의 방법은 이소시안산에스테르(III)과 알코올류 혹은 메르캅탄류(IV)와의 반응이며, 통상의 방법에 의해서 실시된다. 이들의 반응은 불활성 용매(예를 들면, 벤젠, 톨루엔 등의 탄화수소류, 클로로포름, 테트라히드로푸란, 디메틸포름아미드, 디메틸술폭사이드)의 존재하 혹은 부존재하에, 필요에 따라서 염기탈산제(예를 들면, 트리에틸아민, 피리딘)를 첨가하고, 실온하 또는 냉각하 흑은 가열하에 실시하면 좋다. 본 발명의 방법에서 원로물질로서 사용되는 이소시안산 3-이속사졸릴에스테르(III)는 다음식으로 표시되는 바와 같이 상응하는 카르본산(VIII) 또는 아민(X)으로부터 유도된다.
상기 식에서
R, R3및 X는 전술한 바와 같다.
본 발명의 방법은 이소시안산에스테르(III)를 경유하여 목적물질(I)을 제조하는 한, 산 아지드(IX)에 알코올류 또는 메르캅탄류(VI)를 가열반응시키는 방법 및 카아본산(VIII)에 디페닐린산아지드 등의 아지드화제와 알코올류 또는 메르캅탄류(IV)를 가열반응시키는 방법을 포함한다.
본 발명 방법에 의한 이속사졸 유도체(I)은 신규 물질이며, 제초제, 살조제(殺藻劑) 또는 이들의 합성중간체로서 유용하다.
이하에 본 발명 방법의 실시예를 나타낸다.
[실시예 1]
이소시안산 5-t-부틸-3-이속사졸릴에스테르 3.10g을 벤젠 51ml에 현탁시키고, 여기에 1-프로피틸알코을 1.18g을 가하고, 3시간 환류시킨다. 냉각 후, 반응액으로부터 용매를 유거하여, N-(5-t-부틸-3-이속사졸릴) 카르바미드산 1-프로피닐에스테르 4.05g을 얻었다. 본품을 벤젠에 의해 재결정하면 융점 126.5∼127.5℃의 결정을 얻는다.
[실시예 2∼11]
하기의 원료물질(III)을 사용하고, 실시예 1과 동일하게 반응을 행하여 대응하는 목적물질(I)을 얻었다.
주) 표 중의 약호는 하기의 의미를 갖는다.
Al(아릴기), Bz(벤질기), IR(적외선흡수스펙트라), H(수소),
Me(메틸기), Bu(부틸기), Ph(페닐기), Pr(프로필기), t-(3rmq-), mp(융점), bp(비점).
Claims (1)
- 다음 일반식(III)의 이소시안산 3-이속사졸릴 에스테르와 다음 일반식(IV)의 알코을류 또는 메르캅탄류를 반응시킴을 특징으로 하여 다음 일반식(I)의 3-이속사졸릴 카르바미드산에 스테르 또는 3-이속사졸릴티오카르바미드산 S-에스테르의 제조법.
상기 식에서,R은 수소, 탄소수 2이상의 알킬기 또는 아릴기를 나타내며,R2는 알킬기, 알케닐기, 알키닐기, 아르알킬기 또는 아릴기를 나타내고,X는 수소, 알킬기 또는 할로겐을 나타내며,Y는 산소 또는 황을 나타내고,R파 X는 연결하여 알킬렌기를 형성해도 좋고, 상기 알킬기, 아르알킬기 및 아릴기는 할로겐, 알킬기, 알콕시기 및 히드록시로부터 선택된 1이상의 치환기를 가져도 좋다.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR1019800000199A KR800000385B1 (ko) | 1974-12-10 | 1974-12-10 | 이속사졸 유도체의 제조법 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR1019800000199A KR800000385B1 (ko) | 1974-12-10 | 1974-12-10 | 이속사졸 유도체의 제조법 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR800000385B1 true KR800000385B1 (ko) | 1980-05-12 |
Family
ID=19199024
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019800000199A KR800000385B1 (ko) | 1974-12-10 | 1974-12-10 | 이속사졸 유도체의 제조법 |
Country Status (1)
| Country | Link |
|---|---|
| KR (1) | KR800000385B1 (ko) |
-
1974
- 1974-12-10 KR KR1019800000199A patent/KR800000385B1/ko active
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