JPS61165339A - アミド化合物の製造方法 - Google Patents

アミド化合物の製造方法

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Publication number
JPS61165339A
JPS61165339A JP60004107A JP410785A JPS61165339A JP S61165339 A JPS61165339 A JP S61165339A JP 60004107 A JP60004107 A JP 60004107A JP 410785 A JP410785 A JP 410785A JP S61165339 A JPS61165339 A JP S61165339A
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JP
Japan
Prior art keywords
substituted
group
unsubstituted
compound
groups
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.)
Granted
Application number
JP60004107A
Other languages
English (en)
Other versions
JPH0259806B2 (ja
Inventor
Shozo Kato
加藤　祥三
Hidenori Okamoto
岡本　秀則
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Tokuyama Corp
Original Assignee
Tokuyama Corp
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Tokuyama Corp filed Critical Tokuyama Corp
Priority to JP60004107A priority Critical patent/JPS61165339A/ja
Priority to DE8686100362T priority patent/DE3662783D1/de
Priority to EP86100362A priority patent/EP0189774B1/en
Priority to KR1019860000210A priority patent/KR900003270B1/ko
Priority to CN86100282A priority patent/CN1009824B/zh
Publication of JPS61165339A publication Critical patent/JPS61165339A/ja
Publication of JPH0259806B2 publication Critical patent/JPH0259806B2/ja
Granted legal-status Critical Current

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    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
    • C07D207/32—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C07D207/33—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms with substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C07D207/335—Radicals substituted by nitrogen atoms not forming part of a nitro radical
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    • C07D209/04—Indoles; Hydrogenated indoles
    • C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
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    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
    • C07D213/72—Nitrogen atoms
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    • 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
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    • C07D233/56—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 only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
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    • C07D239/20—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D239/22—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms directly attached to ring carbon atoms
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    • C07D239/26—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
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    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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, directly attached to ring carbon atoms
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    • C07D307/70—Nitro radicals
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  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
  • Quinoline Compounds (AREA)
  • Thiazole And Isothizaole Compounds (AREA)
  • Furan Compounds (AREA)
  • Pyridine Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Pyrane Compounds (AREA)
  • Indole Compounds (AREA)
  • Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
  • Hydrogenated Pyridines (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Heterocyclic Compounds Containing Sulfur Atoms (AREA)
  • Pyrrole Compounds (AREA)

Abstract

(57)【要約】本公報は電子出願前の出願データであるた
め要約のデータは記録されません。

Description

【発明の詳細な説明】 （産業上の利用分野） 本発明は、医・農薬あるいけ該原料・中間体として有用
であるアミド化合物の新規な製造方法を提供するもので
ある。　　。
（従来の技術及び発明の解決しようとする問題点） 本発明者らは、シック塩基化合物を原料としたＮ−置換
−アミド化合物の合成及びその生理活性の研究を行なっ
てきた。例えば本発明者らは特願昭５８−１１１０７７
号（特開昭６０−　　　　　　号）に於込て一般式、（
但し、Ａはハロゲン原子、アルコキシ基。
又はアルキルチオ基であり、Ｒ１＊　Ｒ２＃及びＲ３は
それぞれ同種又は異種の水素原子、ハロゲン原子、アル
キル基、アルコキシ基、又はアルキルチオ基である。）
で示されるＮ−置換−クロロアセトアニリドが除草剤と
して極めて有用であることを提案した。
該Ｎ−置置換ジクロロアセトアニリド製法は一般にシッ
ク塩基化合物を原料とし下記式のように還元工程に続き
、クロロアセチル化工程を経て初めて合成される。
即ち、シック塩基を原料とすると目的物まで二段階の反
応を行なわなければならず、しかも還元に際しては、水
素化アルミニウムリチウム等の高価で、取り扱いの難し
い化合物を用いなければいけない場合もあり、工業的に
技術課題が残存していた。
（問題点を解決するための手段及び効果）本発明者らは
、前記アミド化合物の簡単な合成方法について鋭意研究
を行なってきた。
その結果、シック塩基化合物、シラン化合物及びカルボ
ン酸誘導体とを反応させることにより、実に驚くべきこ
とに一段で容易にアミド化合物を合成し得ることを見い
出し、本発明を完成するに至った。
即ち、本発明は、 （イ）一般式（Ｉ）　　Ｒ’−ｃａ＝Ｎ−Ｒ”（但し、
Ｒ１及びＲ２は同種又は異種の置換もしくは非置換アル
キル基、置換もしくは非置換アルケニル基、置換もしく
は非置換アルキニル基、置換本しくは非置換アリール基
。
置換本しくは非置換ヘテロアリール基、置換もしくは非
置換シクロアルキル基、置換もしくは非置換シクロアル
ケニル基、又は置換もしくは非置換ヘテロシクロアルキ
ル基である。）で示されるシッフ塩基化合物、 （ｅ＋）　　一般式（ＩＩ）　　Ｈａ　１ＸＹＺ（但し
、Ｘ、Ｙ、及びＺは同種又は異種の水素原子又はハロゲ
ン原子である。） で示されるシラン化合物、及び ｅ＊　　一般式（ＩＩＩ）　　Ｒ５ｃ　ＯＭ（但し、Ｒ
５け上記Ｒ１と同じ、Ｍけ）〜ロゲン原子及び　０ＣＲ
５基である。） で示されるカルボン酸誘導体とを反応させる（但し、Ｒ
１、Ｒ２及びＲ３は上記と同じである。）で示されるア
ミド化合物の製造方法である。
本発明に於ける原料の一つであるシッフ塩基化合物は前
記一般式（１）即ち、Ｒ１−Ｃ！Ｈ−Ｎ−Ｒ２で示され
る化合物である。上記一般式（Ｉ）中、Ｒ１及びＲ２で
示される基としては種々の有機基のものが公知であり、
本発明に於いてもこれらの公知の有機基が特に限定され
ず使用出来る。一般に好適に使用されるＲ１及びＲ２は
、置換もしくけ非置換のアルキル基、置換もしくは非置
換のアルケニル基、置換もしくは非置換のアルキニル基
、置換もしくけ非置換のアリール基、置換もしくは非置
換のヘテロアリール基、置換もしくは非置換のシクロア
ルキル基、置換もしくは非置換のシクロアルケニル基、
又は置換もしくは非置換のヘテロシクロアルキル基であ
る。工業的に広く利用される該有機基をより具体的に例
示すると次のようなものがある。
上記非置換アルキル基としては、メチル。
エチル、フロビル、フルオロメチル、ヘキシル、ヘプチ
ル、オクチル、ノニル、テシル。
ウンデシル、及びドデシル等の直鎖状又は分校状アルキ
ル基である。前記置換アルキル基としては、フルオロメ
チル、トリフルオロメチル、クロロメチル、トリクロロ
メチル、クロロエチル、ブロモエチル、フルオロプロピ
ル、クロロプロピル、クロロブチル、フロモベンチル、
クロロヘキシル、及ヒフルオロオクチル等の直鎖状又は
分枝状ハロアルキル基：メトキシメチル、メトキシエチ
ル、メトキシプロピル、メトキシブチル、メトキシペン
チル、メトキシヘキシル、エトキシメチル。
エトキシエチル、エトキシプロピル、エトキシブチル、
プロポキシメチル、プロポキシエチル、プロポキシプロ
ピル、プロポキシブチル、ブトキシメチル、ブトキシエ
チル、ブトキシプロピル、ブトキシブチル、及びペント
キシエチル等の直鎖状又は分枝状のアルコキシアルキル
基：フエノキシメチル、フェノキシエチル、及ヒクロロ
フエノキシブロビル等のフェノキシアルキル基ニジアノ
エチル、シアノプロピル及びシアノブチル等のシアノア
ルキル基：ニトロエチル、ニトロプロピル。
及ヒニトロヘキシル等のニトロアルキル基；メチルチオ
メチル、メチルチオエチル、メチルチオプロピル、エチ
ルチオメチル、エチルチオエチル、エチルチオブチあ及
びプロピルチオエチル等のアルキルチオアルキル基：７
工二ルメチル、フェニルエチル、フェニルプロピル、及
びメチルフェニルメチル等のアリールアルキル基：チェ
ニルメチル、チェニルエチル、メトキシチェニルメチル
、フリルメチル、フリルエチル、クロロフリルメチル。
ピロリルメチル、及びピラゾリルメチル等のヘテロアリ
ールアルキル基ニジクロプロピルメチル、及びシクロヘ
キシルエチル等のシクロアルキルアルキル基：メトキシ
力ルゲニルメチル、メトキシカルゲニルエチル、エトキ
シカルボニルメチル、エトキシカルボニルエチル、及び
エトキシカルボニルプロビル等のアルコキシカルボニル
アルキル基等が挙ケラレる。
前記非置換アルケニル基としては、エチニル、フロベニ
ル、フチニル、ペンテニル、ヘキセニル、及びオクテニ
ル等の各種位置異性体のアルケニル基である。また前記
置換アルケニル基としては、クロロエチニル、フルオロ
エチニル、フロモプロペニル、クロロフチニル、クロロ
ペンテニル、及ヒフルオロへキセニル等ノハロアルケニ
ル基：メトキシエテニル、メトキシプロペニル、エトキ
シブテニル、エトキシへキセニル、及びプロポキシブテ
ニル等のアルコキシアルケニル基：シアノエテニル、ニ
トロプロベール、　シｙｔチルアミノエチニル、及びメ
チルチオプロペニル等が挙げられる。
更に前記非置換のアルキニル基としては、エチニル、プ
ロピニル、フチニル、ペンチニル、及びヘキシニル等の
アルキニル基である。
また前記置換アルキニル基としては、クロロプロピニル
、ブロモブチニル、メトキシブチニル、シアノプロピニ
ル、及びメチルチオエチル等が挙げられる。
更にまた前記非置換アリール基としては、フェニル、ナ
フチル、及びアントラニル、フェナンスレニル等のアリ
ール基である。また前記置換アリール基としては、メチ
ルフェニル＋　’）メチルフェニル、エチルフェニル、
ジエチルフェニル、フロビルフェニル、シフロピルフェ
ニル、ブチルフェニル、ペンチルフェニル、ヘキシルフ
ェニル、メチルエチルフェニル、メチルプロピルフェニ
ル、及ヒエチルプロビルフヱニル等のアルキルフェニル
基：フルオロフェニル、ジフルオロフェニル。
クロロフェニル、ジクロロフェニル、フロモフェニル、
ヨードフェニル＋　）　＋）ｙロロフェニル及ヒクロロ
フルオロフェニル等ノハロフェニル基：メトキシフェニ
ル、ジメトキシフェニル、トリメトキシフェニル、エト
キシフエニル、ジェトキシフェニル、プロポキシフェニ
ル、及びブトキシフェニル等のアルコキシフェニル基；
シアノフェニル、ニトロフェニル、クロロ（メチル）フ
ェニル、りａ口（エトキシ）フェニル、メチル（メトキ
シ）フェニル、メチルチオフェニル、トリフルオロメチ
ルフェニル、ビス（クロロエチル７ミ／）フェニル、ニ
トロ（メチル）フェニル、及ヒジフェニル等の置換フェ
ニル基：メチルナフチル、ジメチルナフチル、エチルナ
フチル。
クロロナフチル、ジクロロナフチル、メトキシナフチル
、メチルチオナフチル、ニトロナフチル、及びシアノナ
フチル等の置換ナフチル基等が挙げられる。
更にまた前記非置換ヘテロアリール基としては、フリル
、チェニル、ピロリル、ピリジル、ピリミジル、ベンゾ
フリル、ベンゾチェニル、インドリル、キノリル、チア
ゾリル。
ピラゾリル、ベンゾチアゾリル、チアジアゾリル、及び
オキサシリル等である。また前記置換ヘテロアリール基
としては、メチルフリル、ジメチルフリル、エチルフリ
ル、プロピルフリル、クロロフリル、ブロモ７リル、メ
トキシフリル、エトキシフリル、プロポキシフリル、メ
チルチオフリル、エチルチオフリル、及びニトロフリル
等の置換フリル基；メチルチェニル、エチルチェニル、
フロビルチェニル、フチルチェニル、フルオロチェニル
。
クロロチェニル、ブロモチェニル、ヨードチェニル、メ
トキシチェニル、エトキシチェニル、プロポキシチェニ
ル、メチルチオチェニル、エチルチオチェニル、及ヒニ
トロチェニル等の置換チェニル基；Ｎ−メチルピロリル
。
Ｎ−エチルピロリル、メチル−Ｎ−メチルピロリル、ク
ロロ−Ｎ−エチルピロリル、メトキシ−Ｎ−メチルピロ
リル、メトキシプロリル、エチルピロリル、及ヒクロロ
ピロリル等の置換ビｏ　ｌル基：メチルビリジル、エチ
ルピリジル、クロロピリジル及びメトキシピリジル等の
置換ピリジル基；メチルベンゾフリル、クロロベンゾフ
リル、エトキシペンツＺＩｊ＃、及ヒニトロベンゾフリ
ル等の置換ヘンシアリル基：エチルベンゾチェニル、フ
ルオロベンゾチェニル、メトキシベンゾチェニル。
及ヒニトロペンゾチェニル等の置換ベンゾチェニル基；
メチルキノリル、エチルキノリル。
クロロキノリル、及びメトキシキノリル等の置換キノリ
ル基；メチルチアゾリル基等が挙げられる。
更にまた前記非置換シクロアルキル基としては、シクロ
プロピル、シクロブチル、シクロペンチル、及びシクロ
ヘキシル等のシクロアルキル基である。また前記置換シ
クロアルキル基としては、メチルシクロプロピル、エチ
ルシクロプロピル、プロピルシクロプロビル、クロロシ
フｏ　７’　ａ　ヒル、メトキシシクロプロピル、エト
キシシクロプロピル、メチルシクロブチル、ブロモシク
ロブチル、メチルチオシクロブチル、クロロシクロペン
チル。
メチルシクロヘキシル、エチルシクロヘキシル、りａ口
シク口ヘキシル、メトキシシクロくキシル、及びプロポ
キシシクロヘキシル等が挙げられる。
非置換シクロアルケニル基としては、シクロブテニル、
シクロペンテニル、及ヒシクロへキセニル等である。ま
た前記置換シクロアルケニル基としては、メチルシクロ
ブテニル。
りａロシクａペンテニル、メトキシシクロペンテニル、
メチルシクロヘキセニル、エチルシクロヘキセニル、ク
ロロシクロへキセニル。
メトキシシクロへキセニル、及びエトキシシクロへキセ
ニル等が挙げらレル。
更にまた前記非置換のヘテロシクロアルキル基としては
、テトラヒドロフリル、テトラヒドロチェニル、ピロリ
ジル、テトラヒドロピリル、テトラヒドロチオピリル、
及びピペリジル等である。また前記置換ヘテロシクロア
ルキル基としては、Ｎ−メチルピロリジル。
Ｎ−エチルピロリジル、Ｎ−メチルピペリジル、及びＮ
−エチルピペリジル等が挙げられる。
以上列挙した基を有する化合物には多くの場合、種々の
位置異性体が存在するが、特に限定されず本発明に供す
ることができる。例えばメチルフェニル基としては、０
−メチルフェニル基１ｍ−メチルフェニル基、及ヒｐ−
メチルフェニル基が挙げられ、ブチル基としてはｎ−ブ
チル基、　５ｅｃ−ブチル基、及びｔｅｒｔ−ブチル基
が挙げられる。
更にまた、置換基は以上の具体例に限定されるものでは
なく、本発明の製造方法によって目的物のアミド化合物
が得られるものであれば必要に応じて適宜選択して使用
出来る。
本発明の原料の他の１つは前記一般式（ｎ）即ち、Ｈ８
１ＸＹＺで示されるシラン化合物である。該一般式（Ｉ
ｔ）中の、Ｘ、Ｙ及びＺけ同稽又は異種の水素原子又は
ハロゲン原子が特に制限されず用いられる。該・・ロゲ
ン原子としては塩素、臭素、ヨウ素又はフッ素の各原子
が特に制限されず使用出来るが、特に塩素原子と臭素原
子は好適である。工業的に特に好適に使用される上記シ
ラン化合物を具体的に例示すると、Ｈ８１Ｃｔ３　　、
Ｈ８１Ｂｒ５　。
Ｈ２Ｆ３ｉ、Ｏ１２、Ｈ２Ｓ１Ｂｒ２　１　　Ｈ３Ｓｉ
Ｂｒ等の化合物である。
本発明の更に他の原料の１つは一般式（ＩＩ）即ち、Ｒ
５００Ｍで示されるカルボン酸誘導体である。該カルボ
ン酸誘導体中のＲ３は前記一般式（Ｉ）に於けるＲ１又
けＲ２と同様に定義される置換基である。また上記一般
式（１）中、Ｍはハロゲン原子又は　０ＣＲ５基である
。
該Ｍがハロゲン原子の場合には、Ｒ５ＣＯＭは酸ハロゲ
ン化物を表わし、ハロゲン原子としてはフッ素原子、塩
素原子、臭素原子、及びヨウ素原子が特く限定されず用
いられる。工業的には、Ｍが塩素原子又は臭素原子であ
る酸クロライド又は酸ブロマイドが特に好適に、１１ 使用される。また、Ｍ　ｂｓ　　ＯＣＲ５基で表わされ
る場合、即ち　Ｒ’Ｃ００ＣＲ’は酸無水物を○ 表わす。工業的に一般に好適に使用される本のを具体的
に例示すれば酸ハロゲン化物としでは例えば、酢酸クロ
ライド、酢酸ブロマイド、クロロ酢酸クロライド、ジク
ロロ酢酸クロライド、ブロモ酢酸ブロマイド、ヨード酢
酸クロライド、ジブロモ酢酸クロライド、メトキシ酢酸
クロライド、シアン酢酸クロライド、トリフルオロ酢酸
フルオライド、プロピオン酸クロライド、クロロプロピ
オン酸クロライド、ブロモプロピオン酸ブロマイド、酪
酸クロライド、クロロ酪酸クロライド、吉草酸クロライ
ド、クロロ吉草酸クロライド、ヘキサン酸クロライド、
アクリル酸クロライド。
ブテノン酸クロライド、クロロブテノン酸クロライド、
ペンテン酸クロライド、クロロペンテン酸クロライド、
プロピオル酸クロライド、フェニルプロピオン酸クロラ
イド、フェニルプロペノン酸クロライド、フリルアクリ
ル酸クロライド、安息香酸クロライド、安息香酸ブロマ
イド、メチル安息香酸クロライド。
エチル安息香酸ブロマイド、クロロ安息香酸クロライド
、フルオロ安息香酸フルオライド。
ｙｔ　）　＊　シアン酢酸クロライド、クロロ（メチル
）安息香酸クロライド、シアノ安息香酸クロライド、フ
ェニル安息香酸クロライド、ニトロ安息香酸クロライド
、７０イルクロライド、チオフェンカルボン酸クロライ
ド、インドールカルボン酸クロライド、ピコリンクロラ
イド、シクロプロパンカルボン酸クロライド等が好適で
ある。
また酸無水物としては無水酢醒、無水プロピオン酸、無
水トリフルオロ酢酸、無水クロロ酢酸、無水安息香酸等
が好適に使用される。
本発明に於ける前記原料の反応は、無溶媒で行なうこと
もできるが、一般には溶媒中で行なうのが好ましい。該
溶媒としては、共存する原料、例えばシラン化合物及び
カルボン酸誘導体等と相互作用しない不活性な有機溶媒
であれば限定されず使用出来る。一般にはベンゼン、ト
ルエン、クロロホルム、及ヒアセトニトリル等が好適に
使用される。また該反応に於ける原料の仕込みモル比は
特に限定されるものではないが、副生成物の増加及び経
済性を考慮すると、シック塩基１モルに対してシラン化
合物を１〜２モル、カルボン酸誘導体を１〜１．２モル
の割合で使用するのが好ましい。特にカルボン酸誘導体
を多量に用いると副反応が起こりやすぐなる傾向が認め
ン鳥れる場合もあるので、予め該原料の仕込みモル比を
決定して使用するのがよい。
尚本発明で用いる原料であるシック塩基化′金物は必ず
しも単離、精製したものでなくても良い。即ち、アルデ
ヒド及びアミンから共沸脱水等によりシッフ塩基化合物
を合成し、そのまま、次に本発明で用いる他の原料であ
るシラン化合物及びカルボン酸誘導体を加えて反応させ
ても良い。
また前記反応に於ける反応温度は特忙限定されず広い温
度範囲で選ぶことができるが、原料の化学反応性や生成
物であるアミド化合物の安定性等を考慮して好適とする
温度範囲で反応を行なうことが好ましく、一般には一２
０°Ｃ〜１５０℃の範囲から選べばよい。
更にまた反応時間は反応温度によっても異なるが、一般
には数分から数日例えば５分〜１０日の間で選べばよい
。
本発明の前記一般式（Ｉ）　、　（Ｉｔ）及び（’ＩＩ
Ｉ）で示される各原料の添加順序は特に限定されず必要
に応じて選べばよい。一般にはシック塩基化合物に室温
又は冷却下にて、シラン化合物及びカルボン酸誘導体を
添加すれば良い。
°また、シラン化合物及びカルボン酸誘導体の溶液にシ
ック塩基化合物を添加しても良い。
これらの場合、一般に溶媒を用いる場合が多く、溶媒中
にシッフ塩基化合物、シラン化合物、及びカルボン酸誘
導体の三成分を添加反応させてもよく、各成分を該溶媒
に溶解しておき、この溶媒をそれぞれ添加混合して反応
させて本よ−。
本発明に於いては前記一般式（Ｉ）〜（ＩＩＩ）で示さ
れる原料を反応させることによって簡単にアミド化合物
を得ることが出来る。上記反応で得られるアミド化合物
の精製方法は、特に限定される本のではない。一般には
反応終了後、常圧、減圧もしくは真空蒸留を行なえば良
く、必要に応じて洗浄、再結晶、又はクロマトグラフに
よる精製方法もｍ−ることができる。また、アミド化合
物が高沸点である場合には、反応終了後、溶媒等の低沸
点成分を除去した後、再び溶媒に溶解させ、水洗。
希γルカリ水溶液で洗浄した後に溶媒を除去することに
より、未反応のシラン化合物、カルボン酸誘導体、及び
副生成物のシラン化合物等を容易に除去し、目的とする
アミド化合物を純粋に得ることもできる。
（作用及び効果） 本発明の反応を化学式で示せば、下記の通りである。
上記反応の反応機構は明確ではないが、次のように推論
される。まず一つの反応機構としてシラン化合物の存在
下、シッフ塩基化合物とカルボン酸誘導体とが相互作用
して、中間体としてインモニウム塩型の化合物 これらの化合物とシラン化合物が反応することにより目
的とするアミド化合物が生成すると考えられる。
またもう一つの反応機構として、シック塩基化合物とシ
ラン化合物とがまず反応して、生成し、その後にアミド
化反応が起こる可能性も考えられる。
本発明方法によって得られるアミド化合物は、例えば、
除草剤、殺虫剤、及び殺菌剤等の農薬あるいは医薬品等
に有用である。またこれらの用途の中間原料としても有
用な物質である。
以上のように、本発明の方法は、医農薬等に有用である
アミド化合物を、対応するシック塩基化合物から、温和
な条件で、収車よくしかも一段で合成することができる
優れた方法である。さらに反応終了後の生成物の精製も
容易に行なうことができる。従って本発明は、工業的に
も極めて優れたものであると言える。
（実施例） 以下に、本発明を具体的に説明するために実施例を挙げ
るが、本発明はこれらの実施例に限定されるものではな
い。
実施例　１ ３つロフラスコに、２−１−メトキシ）−チェニルメチ
リデン−２’、６’−ジメチルアニリン（２，４９ｔ　
）の乾燥ベンゼン（１５ｍ）溶液を入れ、窒素下、室温
にて攪拌しながら、トリクロロシラン（２，４８ｔ　）
の乾燥ベンゼン（５−）溶液を徐々に滴下した。次いで
、クロロアセチルクロライド（１，２２ｔ　）の乾燥ベ
ンゼン（５−）溶液を徐々に添加した。
室温にて２時間攪拌した後、低沸点成分を除去して得ら
れた粘稠液体を再びベンゼン（５〇−）に溶解した。ベ
ンゼン溶液を水洗、希アルカリ水溶液で洗浄した後、無
水硫酸ナトリウムで乾燥した。ベンゼンを除去して得ら
れた粘稠液体を真空乾燥して、淡かっ色囲体（３，３Ｏ
ｆ　）を得た。本化合物を蒸留すると沸点１７２℃／　
Ｏ−１５［Ｈｙであった。
本化合物の赤外吸収スペクトルを測定したところ、５１
００〜２８００ｃｒＲ−’にＯ−Ｈ結合に基ツく吸収、
１６７０〇Ｍ−’にアミド基のカルボニル結合に基づく
強い吸収を示した。
その元素分析値は０５９．３７％、Ｈ５，８９％、Ｎ４
．０５％であって、組成式０１４Ｈ１８Ｎ５ｏ２ａｔ　
（３２５，８４）　　に対する計算値である０　５９．
５５％、Ｈ５，６１％、　Ｎ　４．５５％に良く一致し
た。
また、°質量スペクトルを測定したところ、ｍ　／　ｅ
　３２５に分子量に対応する分子イオンピークｖ　Ｍｅ
＝　ｍ　／　ｅ　２８８にＭ”−ａｔに対応するピーク
、ｍ／ｅ２４６にＭｅ−ｃｏＣＨ２ｃｔに対応するピー
ク、ｍ／ｅ１２７（１００％）した。
さらに、′Ｈ−核磁気共鳴スベクトル（δ：ｐｐｍ　：
テトラメチルシラン基準１重クロロホルム溶媒）を測定
した結果を第３図に示した。
その解析結果は次のとおりである。
（ｅ） １．９５　ｐｐｍにプロトン６個分の単一線を示し、フ
ェニル基の２及び６位に置換した（ｆ）のメチルプロト
ンに相当する。５．５０　ｐｐｍにプロトン６個分の単
一線を示し、（ａ）のメチルプロトンに相当する。５．
７２　ｐｐｍにプロトン２個分の単一線を示し、（ｅ）
のメチレンプロトンに相当する。４．７５　ｐｐｍにプ
ロトン２個分の単一線を示し、（ｄ）のメチレンプロト
ンに相当する。６．５５　ｐｐｍにプロトン２個分の四
重線を示し、（ｂ）及び（ｅ）のチオフェン環のプロト
ン２個分する。７．００〜７．４５ｐｐｍにプロトン３
個分の多重線を示し、（ｇ）　、　（ｈ）　、及び（ｉ
）のべンゼン環のプロトンに相当する。
上記の結果から、単離生成物がＮ−Ｃ２’−（３′−メ
トキシ）−チェニルメチル］−Ｎ−クロロアセト−２，
６−ジエチルアニリドであることが明らかとなった。組
数率は９３％であった。
実施例　２ 実施例１と同様の反応を、溶媒としてアセトニトリルを
用いて行なった。反応終了後、低沸点成分を除去して得
られた粘稠液体を、真空乾燥すると固体となった。本化
合物をヘキサンから再結晶することにより、Ｎ　−［２
’−（ｓ’−メトキシ）−チェニルメチル〕−Ｎ−クロ
ロアセト−２，６−ジエチルアニリドの白色結晶を得た
。収率は５５％であった。
実施例　６ フラスコに、２−（Ｎ−メチルピロリル）−メチリデン
−２’、６’−ジエチルアニリン（２，４０ｒ　＞の乾
燥ベンゼン（２０ｍ）溶液を入れ、窒素下、室温にて攪
拌しながら、クロロアセチルクロライド（１，４２ｆ　
’）の乾燥ベンゼン（５−）溶液を徐々に添加した。次
いで、トリクロロシラン（２，３８ｆ　’）　（Ｄ乾燥
ベンゼン（１０ｇ４）溶液を添加した。滴下終了後、油
浴中（５０°Ｃ）にて１時間加熱攪拌した。減圧にて低
沸物を除去して得られた粘稠液体をカラムクロマトグラ
フ（て精製を行ない、淡かっ色面体である下記式で示さ
れるＮ’−［２−（ａ−メチルピロリル）−メチル〕−
Ｎ’−クロロアセｈ−２’、６’−ジエチルアニリドを
得た。収率は６４％であった。
実施例　４ ｎ−ヘキシルアルデヒド（１，５５ｆ　）　。
２．６−ジエチルアニリン（２，２ａｒ）、及びベンゼ
ン（５０ｖ）の混合物を油浴上で１時間加熱還流するこ
とにより°共沸脱水を行なった。その溶液に、室温にて
攪拌しながらクロロアセチルクロライド（１，７９Ｆ　
）の乾燥ベンゼン（５−）溶液、次いでトリクロロシラ
ンｉ、４ｏｒ）の乾燥ベンゼン（５−）溶液を添加した
。滴下終了後、油浴中（４０℃）にて２時間加熱攪拌し
た。低沸点成分を減圧にて除去して得られた粘稠液体を
エーテル（５０−）に溶解した。エーテル溶液を水で洗
浄した後、無水硫酸ナトリウムで乾燥した。
エーテルを除去して得られた液体を蒸留して、沸点１５
２℃／　０．２　ｖｍＨｙである下記式で示されるＮ−
（ｎ−ヘキシル）−Ｎ−クロロアセ）−２，６−ジエチ
ルアニリドを得た。収率け２．６−ジエチルアニリンに
対し、５５ＣＯＯＨ２０を 実施例　５ 実施例１，２．及び３に記載した方法と同様ニ、シラン
化合物としてトリクロロシランを用いて、各種アミド化
合物の合成を行なった。得られたアきド化合物の構造式
、物性。
及び収率を第１表に記載した。
以下余白 実施例　６ 種々のシッフ塩基化合物、稲々のシラン化合物、及び種
々のカルボン酸誘導体を用いて、アミド化合物の合成を
行なった。構造式及び収率を第２表に記載した。表中の
Ｒ’　＋　Ｒ２＊Ｒ５，Ｍｌ及びＨ８１ＸＹＺ　　は下
記式テ示される置換基及び化合物である。
Ｒ５０Ｍ、Ｈ８１ＸＹＺ 以下余白

Claims (1)

    【特許請求の範囲】
  1. （１）（イ）一般式（ I ）　Ｒ＾１−ＣＨ＝Ｎ−Ｒ＾
    ２（但し、Ｒ＾１及びＲ＾２は同種又は異種の、置換も
    しくは非置換アルキル基、置換もしく は非置換アルケニル基、置換もしくは非置 換アルキニル基、置換もしくは非置換アリ ール基、置換もしくは非置換ヘテロアリー ル基、置換もしくは非置換シクロアルキル 基、置換もしくは非置換シクロアルケニル 基、又は置換もしくは非置換ヘテロシクロ アルキル基である。） で示されるシッフ塩基化合物、 （ロ）一般式（II）　ＨＳｉＸＹＺ （但し、Ｘ、Ｙ、及びＺは同種又は異種の 水素原子又はハロゲン原子である。） で示されるシラン化合物、及び （ハ）一般式（III）　Ｒ＾３ＣＯＭ （但し、Ｒ＾３は上記Ｒ＾１と同じであり、Ｍはハロゲ
    ン原子又は▲数式、化学式、表等があります▼基である
    。） で示されるカルボン酸誘導体とを反応させることを特徴
    とする一般式（IV）▲数式、化学式、表等があります▼ （但し、Ｒ＾１、Ｒ＾２及びＲ＾３は上記と同じである
    ）で示されるアミド化合物の製造方法。
JP60004107A 1985-01-16 1985-01-16 アミド化合物の製造方法 Granted JPS61165339A (ja)

Priority Applications (5)

Application Number Priority Date Filing Date Title
JP60004107A JPS61165339A (ja) 1985-01-16 1985-01-16 アミド化合物の製造方法
DE8686100362T DE3662783D1 (en) 1985-01-16 1986-01-13 Process for production of n,n-disubstituted carboxylic acid amides
EP86100362A EP0189774B1 (en) 1985-01-16 1986-01-13 Process for production of n,n-disubstituted carboxylic acid amides
KR1019860000210A KR900003270B1 (ko) 1985-01-16 1986-01-15 N,n-2 치환된 카르복실산 아미드류의 제조방법
CN86100282A CN1009824B (zh) 1985-01-16 1986-01-15 N，n-二代羧酸酰胺类的制造方法

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP60004107A JPS61165339A (ja) 1985-01-16 1985-01-16 アミド化合物の製造方法

Publications (2)

Publication Number Publication Date
JPS61165339A true JPS61165339A (ja) 1986-07-26
JPH0259806B2 JPH0259806B2 (ja) 1990-12-13

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JP60004107A Granted JPS61165339A (ja) 1985-01-16 1985-01-16 アミド化合物の製造方法

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EP (1) EP0189774B1 (ja)
JP (1) JPS61165339A (ja)
KR (1) KR900003270B1 (ja)
CN (1) CN1009824B (ja)
DE (1) DE3662783D1 (ja)

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WO2021085635A1 (ja) * 2019-10-30 2021-05-06 学校法人中部大学 アミド反応用反応剤及びそれを用いたアミド化合物の製造方法

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* Cited by examiner, † Cited by third party
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AU2948189A (en) * 1987-12-31 1989-08-01 Smithkline Beckman Corporation 4-aralkyl-5-substituted-1,2,4-triazole-5-thiols
EP1487796A4 (en) * 2002-03-28 2005-11-16 Neurogen Corp SUBSTITUTED BIARYLAMIDES AS MODULATORS OF THE C5A RECEPTOR
US6858637B2 (en) 2002-03-28 2005-02-22 Neurogen Corporation Substituted biaryl amides as C5a receptor modulators
GB0219961D0 (en) * 2002-08-28 2002-10-02 Pfizer Ltd Oxytocin inhibitors
US9394287B2 (en) 2010-11-05 2016-07-19 Senomyx, Inc. Compounds useful as modulators of TRPM8
JP6865743B2 (ja) 2015-10-01 2021-04-28 フィルメニッヒ インコーポレイテッドＦｉｒｍｅｎｉｃｈ Ｉｎｃｏｒｐｏｒａｔｅｄ Ｔｒｐｍ８の活性調節因子として有用な化合物
CN108123175B (zh) * 2016-11-29 2020-05-22 微宏动力系统（湖州）有限公司 一种酰胺化合物的合成方法、酰胺化合物及非水电解液

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2021085635A1 (ja) * 2019-10-30 2021-05-06 学校法人中部大学 アミド反応用反応剤及びそれを用いたアミド化合物の製造方法

Also Published As

Publication number Publication date
EP0189774A1 (en) 1986-08-06
EP0189774B1 (en) 1989-04-12
KR900003270B1 (ko) 1990-05-12
KR860005803A (ko) 1986-08-13
CN86100282A (zh) 1986-07-16
CN1009824B (zh) 1990-10-03
JPH0259806B2 (ja) 1990-12-13
DE3662783D1 (en) 1989-05-18

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