JPH023630A - 2,6-diethyl-4-iodoaniline and production thereof - Google Patents
2,6-diethyl-4-iodoaniline and production thereofInfo
- Publication number
- JPH023630A JPH023630A JP15269088A JP15269088A JPH023630A JP H023630 A JPH023630 A JP H023630A JP 15269088 A JP15269088 A JP 15269088A JP 15269088 A JP15269088 A JP 15269088A JP H023630 A JPH023630 A JP H023630A
- Authority
- JP
- Japan
- Prior art keywords
- iodoaniline
- diethyl
- compound
- present
- production
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- FVNZBIHPUWUTQD-UHFFFAOYSA-N 2,6-diethyl-4-iodoaniline Chemical compound CCC1=CC(I)=CC(CC)=C1N FVNZBIHPUWUTQD-UHFFFAOYSA-N 0.000 title claims abstract description 8
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 8
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims abstract description 5
- 229910052740 iodine Inorganic materials 0.000 claims abstract description 5
- 239000011630 iodine Substances 0.000 claims abstract description 5
- 150000001875 compounds Chemical class 0.000 abstract description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 abstract description 6
- 230000002363 herbicidal effect Effects 0.000 abstract description 4
- 229910000030 sodium bicarbonate Inorganic materials 0.000 abstract description 3
- 235000017557 sodium bicarbonate Nutrition 0.000 abstract description 3
- 239000003905 agrochemical Substances 0.000 abstract description 2
- 125000000217 alkyl group Chemical group 0.000 abstract description 2
- 239000003814 drug Substances 0.000 abstract description 2
- 239000002904 solvent Substances 0.000 abstract description 2
- FOYHNROGBXVLLX-UHFFFAOYSA-N 2,6-diethylaniline Chemical compound CCC1=CC=CC(CC)=C1N FOYHNROGBXVLLX-UHFFFAOYSA-N 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- RRHNGIRRWDWWQQ-UHFFFAOYSA-N n-iodoaniline Chemical compound INC1=CC=CC=C1 RRHNGIRRWDWWQQ-UHFFFAOYSA-N 0.000 description 5
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 229940053202 antiepileptics carboxamide derivative Drugs 0.000 description 2
- 239000011968 lewis acid catalyst Substances 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 101150041968 CDC13 gene Proteins 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- GGSUCNLOZRCGPQ-UHFFFAOYSA-N diethylaniline Chemical compound CCN(CC)C1=CC=CC=C1 GGSUCNLOZRCGPQ-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
【発明の詳細な説明】
（産業上の利用分野）
本発明は、医薬、農薬等の製造中間体として有用な新規
な２，６−ジエチル−４−ヨードアニリン及びその製造
法に関する。DETAILED DESCRIPTION OF THE INVENTION (Field of Industrial Application) The present invention relates to a novel 2,6-diethyl-4-iodoaniline useful as an intermediate in the production of pharmaceuticals, agricultural chemicals, etc., and a method for producing the same.
本発明化合物は、特に除草活性を有するピロン−３−カ
ルボキサミド誘導体（特願昭６２−５３８７３）の製造
中間体として有用である。The compounds of the present invention are particularly useful as intermediates for producing pyrone-3-carboxamide derivatives having herbicidal activity (Japanese Patent Application No. 62-53873).
（従来技術及び発明が解決しようとする課題）本発明化
合物は、本発明者らによって初めて合成された新規化合
物である。本発明者らは、除草活性を有するピロン−３
−カルボキサミド誘導体の製造法について検討した結果
、本発明化合物がその製造中間体として重要であること
およびこの有利な製造法を見い出し本発明に至った。(Prior Art and Problems to be Solved by the Invention) The compound of the present invention is a novel compound synthesized for the first time by the present inventors. The present inventors have discovered that pyrone-3 has herbicidal activity.
- As a result of studying methods for producing carboxamide derivatives, we discovered that the compound of the present invention is important as an intermediate for its production and discovered an advantageous production method thereof, leading to the present invention.
（課題を解決するための手段）
本発明は、２，６−ジニチルー本ヨードアニリン及びそ
の製造法に関する。(Means for Solving the Problems) The present invention relates to 2,6-dinityl iodoaniline and a method for producing the same.
本発明化合物である２、６−ジエチル−４−ヨードアニ
リンは、２，６．ジエチルアニリンにヨウ素を作用させ
ることによって製造することが出来る。用いるヨウ素の
量は、２，６−ジエチルアニリンに対して０．８〜１．
２当量が好ましい。この反応は、１００’Ｃ以下の温度
で行うことができるが、反応上及び操作上室温付近が最
も好ましい。この反応は、不活性溶媒を用いることがで
きるが、特に、エーテル、塩化メチレン、クロロホルム
などが好適に用いられる。これらの溶媒と水との二相系
で反応を行ってもよい。又、この反応において、塩基を
存在させることにより、高収率で、目的物である２、６
−ジニチルー本ヨードアニリンを得ることができる。塩
基としては、ピリジン、トリエチルアミン等の有機塩基
、炭酸水素ナトリウム、炭酸ナトリウム、水酸化ナトリ
ウムなどの無機塩基が挙げられる。これらの塩基の量は
、２，６−ジニチルアニリンに対して当量以上用いるこ
とが好ましい。2,6-diethyl-4-iodoaniline, which is a compound of the present invention, is 2,6-diethyl-4-iodoaniline. It can be produced by reacting diethylaniline with iodine. The amount of iodine used is 0.8 to 1.
2 equivalents is preferred. This reaction can be carried out at a temperature of 100'C or lower, but from the viewpoint of reaction and operation, a temperature around room temperature is most preferable. Although an inert solvent can be used in this reaction, ether, methylene chloride, chloroform, etc. are particularly preferably used. The reaction may be carried out in a two-phase system of these solvents and water. In addition, in this reaction, the presence of a base allows the desired product 2,6 to be produced in high yield.
- Dinitiru iodoaniline can be obtained. Examples of the base include organic bases such as pyridine and triethylamine, and inorganic bases such as sodium hydrogen carbonate, sodium carbonate, and sodium hydroxide. The amount of these bases is preferably equal to or greater than the amount of 2,6-dinitylaniline.
本発明化合物の精製方法は、特に限定されるものではな
い。一般には、−過、抽出、蒸留、カラムクロマトグラ
フィー等によって精製することができる。The method for purifying the compound of the present invention is not particularly limited. Generally, it can be purified by filtration, extraction, distillation, column chromatography, etc.
又、本発明化合物は本ヨードアニリンをルイス酸触媒の
存在下、エチレンを加圧下に作用させることによっても
得ることができる。この場合、ルイス酸触媒として、無
水塩化アルミニウムが好適に用いられる。The compound of the present invention can also be obtained by treating the iodoaniline with ethylene under pressure in the presence of a Lewis acid catalyst. In this case, anhydrous aluminum chloride is preferably used as the Lewis acid catalyst.
尚、本発明化合物２，６−ジニチルー本ヨードアニリン
から、例えば、下記ルートによって一般式（Ｉ）で示さ
れる除草活性を有する化合物が得られる。A compound having herbicidal activity represented by the general formula (I) can be obtained from the compound of the present invention, 2,6-dinityl-pro-iodoaniline, by the following route, for example.
（ｉ）
（Ｒ１，Ｒ２，Ｒ３は低級アルキル基を示す。）以下に
実施例を挙げて本発明をさらに詳しく説明する。(i) (R1, R2, and R3 represent lower alkyl groups.) The present invention will be explained in more detail with reference to Examples below.
（実施例）
２．６−ジニチルアニリン３５．９ｇとエーテル２５０
ｍ１の溶液に炭酸水素ナトリウム４９．５ｇを含む水溶
液４６０ｍ１を加えた。この混合物に撹拌下、ヨウ素５
９．５ｇを１時間１５分かけて加え、さらに、３時間５
０分室温で撹拌した。反応混合物を分液ロートに移して
、有機層をとり、常法により、水洗、乾燥、濃縮し、残
さをクーゲルロール装置を用いて蒸留することにより、
２，６−ジニチルー本ヨードアニリンを５６．５ｇ得た
。(Example) 35.9 g of 2.6-dinitylaniline and 250 g of ether
460 ml of an aqueous solution containing 49.5 g of sodium hydrogen carbonate was added to the ml solution. Add 5 iodine to this mixture under stirring.
Added 9.5g over 1 hour and 15 minutes, and then added 9.5g over 3 hours and 5 minutes.
Stirred at room temperature for 0 minutes. The reaction mixture was transferred to a separating funnel, the organic layer was taken, and the organic layer was washed with water, dried, and concentrated using a conventional method, and the residue was distilled using a Kugelrohr apparatus.
56.5 g of 2,6-dinityl iodoaniline was obtained.
ｂｐ １６０−１７０°Ｃ（ｂａｔｈ） ／ ０．２５
ｍｍＨｇ】ＨＮＭＲ（ＣＤＣ１３）δ１．１８（６Ｈ、
ｔ） 、 ２．４０（４Ｈ、ｑ） 。bp 160-170°C (bath) / 0.25
mmHg] HNMR (CDC13) δ1.18 (6H,
t), 2.40 (4H, q).
３．５０（２Ｈ、ｂｒ） 、 ７．１３（２Ｈ、ｓ）。3.50 (2H, br), 7.13 (2H, s).
Claims (1)
，６−ジエチルアニリンに、ヨウ素を作用させることを
特徴とする２，６−ジエチル−４−ヨードアニリンの製
造法。(1) 2,6-diethyl-4-iodoaniline (2) 2
A method for producing 2,6-diethyl-4-iodoaniline, which comprises reacting ,6-diethylaniline with iodine.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP15269088A JPH023630A (en) | 1988-06-21 | 1988-06-21 | 2,6-diethyl-4-iodoaniline and production thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP15269088A JPH023630A (en) | 1988-06-21 | 1988-06-21 | 2,6-diethyl-4-iodoaniline and production thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH023630A true JPH023630A (en) | 1990-01-09 |
Family
ID=15546004
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP15269088A Pending JPH023630A (en) | 1988-06-21 | 1988-06-21 | 2,6-diethyl-4-iodoaniline and production thereof |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH023630A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5244827A (en) * | 1991-10-31 | 1993-09-14 | Sgs-Thomson Microelectronics, Inc. | Method for planarized isolation for cmos devices |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS54148748A (en) * | 1978-05-01 | 1979-11-21 | Sandoz Ag | 2*66dialkylltrifluoromethane sulfonanilides and their manufacture and use |
| JPS63126847A (en) * | 1986-11-17 | 1988-05-30 | Hokko Chem Ind Co Ltd | N-substitute aniline derivative and production thereof |
-
1988
- 1988-06-21 JP JP15269088A patent/JPH023630A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS54148748A (en) * | 1978-05-01 | 1979-11-21 | Sandoz Ag | 2*66dialkylltrifluoromethane sulfonanilides and their manufacture and use |
| JPS63126847A (en) * | 1986-11-17 | 1988-05-30 | Hokko Chem Ind Co Ltd | N-substitute aniline derivative and production thereof |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5244827A (en) * | 1991-10-31 | 1993-09-14 | Sgs-Thomson Microelectronics, Inc. | Method for planarized isolation for cmos devices |
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