JPH07506819A - Process for producing hydroxyalkanecarboxylic acid amide - Google Patents
Process for producing hydroxyalkanecarboxylic acid amideInfo
- Publication number
- JPH07506819A JPH07506819A JP5518842A JP51884293A JPH07506819A JP H07506819 A JPH07506819 A JP H07506819A JP 5518842 A JP5518842 A JP 5518842A JP 51884293 A JP51884293 A JP 51884293A JP H07506819 A JPH07506819 A JP H07506819A
- Authority
- JP
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- Prior art keywords
- acid
- formula
- chloride
- general formula
- hydroxyalkanecarboxylic
- Prior art date
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
- C07D295/18—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
- C07D295/182—Radicals derived from carboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/02—Preparation of carboxylic acid amides from carboxylic acids or from esters, anhydrides, or halides thereof by reaction with ammonia or amines
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (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。 (57) [Summary] This bulletin contains application data before electronic filing, so abstract data is not recorded.
Description
【発明の詳細な説明】 ヒドロキシアルカンカルボン酸アミドの製法本発明は一般式ｌ： ［式中、ｎは１〜２０の整数であり、Ｒユ及びＲ２は、それぞれ最大８個の炭素 原子を有するアルキル基であるか、又は−緒になって酸素原子又は窒素原子によ り中断されていてよい４〜８個の炭素原子を有するアルキレン基である］のヒド ロキシアルカンカルボン酸アミドを、一般式■： ＨＯ−ＣｎＨ２，−ＣＯＯＨ（ｎ） ［式中、ｎは前記の意味を有する］のヒドロキシアルカンカルボン酸と一般式ｌ ： ［式中、Ｒ１及びＲ２は前記の意味を有する］のアミンとから製造する方法に関 し、これは、ワンショット反応（Ｅｉｎｔｏｐｆｒｅａｋｔｉｏｎ）で、ヒドロ キシアルカンカルボン酸を、酸１モル当たり塩化アセチル１０〜３０モルと共に 還流下で加熱し、アセチル化の実施の後に、過剰な塩化アセチルを留去し、その 残留物を、酸１モル当たり塩化チオニル１．５〜５モルと共に還流下で加熱し、 酸塩化物−形成の実施の後に、塩化チオニルを蒸留により除去し、その残留物を ４〜８個の炭素原子を有するジアルキルエーテル中に溶かし、得られた溶液を、 ０〜１０℃まで冷却されたアミンの水溶液に適当に配分して添加し、アミド形成 の後に、１０℃〜３０℃の反応温度で、水酸化ナトリウム水溶液を用いる処理に より、酢酸塩基を離脱させることを特徴殊に本発明は、一般式■中の基： が、それぞれアルキル基中に１〜４個の炭素原子を有するジアルキルアミノ基で あるか、又は基：［式中、Ｒ８及びＲ４は相互に無関係に水素原子又はメチル基 であり、Ｘはメチレン基、酸素原子又はＮ−ＣＨ３基である］である、一般式Ｉ のヒドロキシアルカンカルボン酸アミドの製造に関する。[Detailed description of the invention] Process for producing hydroxyalkanecarboxylic acid amide The present invention relates to the general formula l: [Wherein, n is an integer from 1 to 20, and R and R each represent a maximum of 8 carbon atoms. an alkyl group having an atom, or - together with an oxygen atom or a nitrogen atom. is an alkylene group having 4 to 8 carbon atoms which may be interrupted by Roxyalkanecarboxylic acid amide, general formula ■: HO-CnH2, -COOH(n) A hydroxyalkane carboxylic acid of the formula [wherein n has the above-mentioned meaning] and a general formula l : [In the formula, R1 and R2 have the above meanings] This is a one-shot reaction (Eintopfreaktion), and the hydro xyalkanecarboxylic acid with 10 to 30 moles of acetyl chloride per mole of acid. After heating under reflux and carrying out the acetylation, excess acetyl chloride is distilled off; heating the residue under reflux with 1.5 to 5 mol of thionyl chloride per mol of acid; After carrying out the acid chloride formation, the thionyl chloride is removed by distillation and the residue is Dissolved in a dialkyl ether having 4 to 8 carbon atoms, the resulting solution is Add the amine in an appropriate proportion to an aqueous solution cooled to 0-10°C to form an amide. followed by treatment with an aqueous sodium hydroxide solution at a reaction temperature of 10°C to 30°C. In particular, the present invention is characterized in that the acetate base is eliminated from the group in the general formula (1): are dialkylamino groups each having 1 to 4 carbon atoms in the alkyl group; or a group: [wherein R8 and R4 are independently a hydrogen atom or a methyl group] and X is a methylene group, an oxygen atom or a N-CH3 group], the general formula I The present invention relates to the production of hydroxyalkanecarboxylic acid amides.
一般式■のヒドロキシアルカンカルボン酸アミドは、公知のように、非常に重要 な中間体及び／又は薬物学的に有用な物賀である。As is known, the hydroxyalkanecarboxylic acid amide of the general formula ■ is very important. It is a useful intermediate and/or pharmaceutically useful product.
例えば、一般式Ｉａ： ［式中、Ｒ６は水素又はアルキル基である］のヒドロキシアルカンカルボン酸ア ミドは、除草剤の製造のための重要な中間体である（ドイツ特許（ＤＥ−Ａ）第 ３０３８５９８号明細書）。For example, general formula Ia: [In the formula, R6 is hydrogen or an alkyl group] hydroxyalkanecarboxylic acid atom Mido is an important intermediate for the production of herbicides (German patent (DE-A) no. 3038598).
一般式Ｉｂ＝ ［式中、ｍは、７〜１８の数である］のヒドロキシアルカンカルボン酸アミドは 、例えば皮膚又は粘膜疾患の局所治療用の薬剤の製造のために好適である（国際 公開第Ｗ０９０１０９３７３号明細書）か、又は、界面活性剤の製造のための中 間体として使用することができる（米国特許（ＵＳ−Ａ）第２９３６３２５号明 細書）。だが、これらのヒドロキシアルカンカルボン酸アミドの合成は、一般に かなり費用がかかり、かつ得られる生成物の収率と純度はしばしば不充分である 。これに反して、本発明のワンショット反応では、生態環境的かつ経済的利点を 提供する。これは、公知方法に比べて比較的簡単に実行可能であり、かつ意外に も高い収率と純度で反応生成物を提供する。General formula Ib= The hydroxyalkanecarboxylic acid amide [wherein m is a number from 7 to 18] is , suitable for example for the production of medicaments for the topical treatment of skin or mucous membrane diseases (International Publication No. W090109373) or for the production of surfactants. (US-A) No. 2,936,325 Specifications). However, the synthesis of these hydroxyalkanecarboxylic acid amides is generally difficult. It is quite expensive and the yield and purity of the products obtained are often inadequate. . On the contrary, the one-shot reaction of the present invention offers ecological and economic advantages. provide. This is relatively easy to implement compared to known methods, and surprisingly It also provides reaction products in high yield and purity.
本発明の方法は次の方法で実施される：ヒドロキシアルカンカルボン酸を、酸１ モル当たり塩化アセチル１０〜３０モル中に溶かすか又は懸濁させ、かっこの反 応混合物を還流下で加熱する。アセチル化の実施の後に（薄層クロマトグラフィ ー分析により、又は塩化水素発生が生じなくなることにより認識可能）、過剰の 塩化アセチルを留去するが、この際、真空適用により、できる限り完全な塩化ア セチルの除去に配慮する次いで得られた残留物に、使用された酸１モル当たり塩 化チオニル１．５〜５モル添加し、かつ得られた混合物を還流下で加熱する。酸 塩化物−形成の実施の後に、塩化チオニルを、前と同じ方法で、前記の塩化アセ チルと同様にできる限り完全に除去し、得られた残留物を４〜８個の炭素原子を 有するジアルキルエーテル中に溶かす。ジアルキルエーテルとしては、例えばジ エチルエーテル、ジイソプロピルエーテル、ジブチルエーテル又は殊にメチル− ｔ−ブチルエーテルが好適である。The process of the invention is carried out in the following manner: a hydroxyalkanecarboxylic acid is added to the acid 1 Dissolved or suspended in 10 to 30 moles of acetyl chloride per mole, The reaction mixture is heated under reflux. After carrying out the acetylation (thin layer chromatography – recognizable by analysis or by the fact that hydrogen chloride evolution ceases to occur). The acetyl chloride is distilled off, applying a vacuum to remove the acetyl chloride as completely as possible. Taking into account the removal of cetyl, the residue obtained then contains salt per mole of acid used. 1.5 to 5 mol of thionyl chloride are added and the resulting mixture is heated under reflux. acid After carrying out the chloride-formation, thionyl chloride is added to the acetate chloride in the same manner as before. Remove as completely as possible in the same manner as for chilling, and use the resulting residue to reduce carbon atoms of 4 to 8 carbon atoms. Dissolve in dialkyl ether with. Examples of dialkyl ether include dialkyl ether. Ethyl ether, diisopropyl ether, dibutyl ether or especially methyl- Tert-butyl ether is preferred.
次いで、酸塩化物のエーテル溶液を、有利には撹拌し、かつ場合により同じエー テルを添加し、０℃〜１０℃に冷却された、アミン有利には２〜５モル（使用さ れた酸１モル当たり）の水溶液に、反応温度が１０℃を超えないように適当に配 分して添加する。次いで、反応混合物を、反応が完全に生じるように室温で更に ２０〜６０分間放置し、かつこれに、過剰量の水酸化ナトリウム水溶液又は−水 ／アルコール溶液を添加し、室温で２０〜６０分間撹拌する。The ethereal solution of the acid chloride is then advantageously stirred and optionally added to the same ether solution. The amine, preferably 2 to 5 mol (used), is added and cooled to 0°C to 10°C. (per mole of acid) in an aqueous solution so that the reaction temperature does not exceed 10°C. Add in portions. The reaction mixture is then further heated at room temperature to ensure complete reaction. Leave to stand for 20 to 60 minutes, and add excess sodium hydroxide aqueous solution or -water. /Add alcohol solution and stir at room temperature for 20-60 minutes.
例えば、有機相を分離し、洗浄し、濃縮し、かつ残留物を再結晶させることによ り精製する常法により、反応混合物の仕上げ処理する。For example, by separating the organic phase, washing, concentrating and recrystallizing the residue. The reaction mixture is worked up by conventional purification methods.
次の実施例は、本発明の方法を詳述するものである一般式Ｉのω−ヒドロキシア ルカンカルボン酸アミドの製造のための一般的方法 ω−ヒドロキシアルカン酸ａｇを塩化アセチルｂｍＺｔ：Ｓ濁させ、還流及び撹 拌下で３０分間加熱する。The following example details the process of the invention, ω-hydroxyacrylates of general formula I. General method for the production of lucancarboxylic acid amides ω-Hydroxyalkanoic acid ag was clouded with acetyl chloride bmZt:S, refluxed and stirred. Heat under stirring for 30 minutes.
次いで、真空中で塩化アセチルを留去し、その残留物に塩化チオニルＣｍｌを添 加し、かつこの混合物を６０℃で１時間加熱する。次いで、真空中で塩化チオニ ルを留去し、かつその残留物を、メチル−ｔ−ブチルエーテルｄｍｌ中に溶かす 。The acetyl chloride was then distilled off in vacuo and thionyl chloride Cml was added to the residue. and heat the mixture at 60° C. for 1 hour. Then add thionichloride in vacuo. and dissolve the residue in dml methyl-tert-butyl ether. .
４０％ジメチルアミン水溶液ｅｍｌに、メチル−ｔ−ブチルエーテルｆｍｌを添 加し、撹拌下で０℃まで冷却する。次いで、反応温度が１０℃を超えないように 、この混合物に、前記の酸塩化物エーテル溶液を滴加導入し、さらに室温で３０ 分間撹拌し、この反応混合物に、メタノールｉｍｊ！と水ｋ ｍ １との混合物 中の水酸化ナトリウムｈｇの溶液を添加し、かつさらに室温で３０分間撹拌する 。Add methyl-t-butyl ether fml to 40% dimethylamine aqueous solution eml. and cool to 0° C. with stirring. Next, the reaction temperature should not exceed 10°C. , the abovementioned acid chloride ether solution was added dropwise to this mixture and the mixture was further heated for 30 minutes at room temperature. Stir for a minute and add methanol imj! to the reaction mixture. and a mixture of water k m 1 Add the solution of sodium hydroxide hg in the solution and stir for an additional 30 minutes at room temperature. .
次いで、この混合物を水及びメチル−ｔ−ブチルエーテルを用いて薄め、有機相 を分離し、洗浄し、かつ真空中で濃縮させる。その残留物を、酢酸エチルエステ ル／ヘキサンから再結晶させると、融点ｍ℃のω−ヒドロキシアルカン酸ジメチ ルアミド１９が得られる（＝理論量のｐ％）。The mixture was then diluted with water and methyl-t-butyl ether and the organic phase Separate, wash and concentrate in vacuo. The residue was extracted with ethyl acetate. When recrystallized from dichloromethane/hexane, dimethyl ω-hydroxyalkanoate with melting point m°C 19 is obtained (=p% of theory).
例１： １３−ヒドロキシトリデカン酸からの１３−ヒドロキシトリデカン酸−ジメチル アミド ＣｒａＨａｘＮＯｓ＋ （２５７，４２）計算値 Ｃ６９，９９Ｒ１２，１４Ｎ ５．４４測定値 Ｃ７０，３８Ｈｌｌ、９８ Ｎ５．４３例２・ １１−ヒドロキシウンデカン酸からの１１−ヒドロキシウンデカン酸−ジメチル アミド Ｃ１６Ｈ３３Ｎ０２（２２７１，４４）計算値 Ｃ６８，０８Ｈｌｌ、８７ Ｎ ６．１１測定値 Ｃ６８，４５Ｈｌｌ、７６ Ｎ６．１３例３： １４−ヒドロキシテトラデカン酸からの１４−ヒドロキシテトラデカン酸−ジメ チルアミドＣ１５Ｈ２７ＮＯＱ（２２９，３６） 計算値 Ｃ７０，８０Ｎ１２．２５ Ｎ５．１６測定値 Ｃ７１，１６Ｎ１２． ２７ Ｎ５．２０例４：１５−ヒドロキシペンタデカン酸からの１５−ヒドロキ シペンタデカン酸−ジメチルアミドＣ１７８１１５ＮＯ２（２８５，４７）計算 値 Ｃ７１，５３Ｎ１２．３６ Ｎ４．９１測定値 Ｃ７１，６５Ｎ１２．１９ Ｎ４．９３例５：１３−ヒドロキシトリデカン酸からの４−（１３−ヒドロキ シ−１−オキソトリデシル）モルホリン Ｃ□７Ｈ３３ＮＯ８（２９９，４５） 計算値 Ｃ６８，１９Ｈｌｌ、１１ Ｎ４．６８測定値 Ｃ６８，１６Ｈｌｌ、 ０３ Ｎ４．７４フロントページの続き （７２）発明者 ネーフ、 ギュンタードイツ連邦共和国 Ｄ−１０００ベルリ ン１５ マルクグラーフーアルブレヒトーシュトラーセ ４ （７２）発明者 キルシュ、 ゲラルトドイツ連邦共和国 Ｄ −１０００ベル リン３３ ルシウスシュトラーセ ６べ一Example 1: Dimethyl 13-hydroxytridecanoate from 13-hydroxytridecanoic acid Amide CraHaxNOs+ (257,42) Calculated value C69,99R12,14N 5.44 Measured value C70, 38Hll, 98 N5.43 Example 2. Dimethyl 11-hydroxyundecanoate from 11-hydroxyundecanoic acid Amide C16H33N02 (2271,44) Calculated value C68,08Hll, 87N 6.11 Measured value C68, 45Hll, 76 N6.13 Example 3: 14-hydroxytetradecanoic acid-dime from 14-hydroxytetradecanoic acid Tyramide C15H27NOQ (229,36) Calculated value C70, 80N12.25 N5.16 Measured value C71, 16N12. 27 N5.20 Example 4: 15-hydroxy from 15-hydroxypentadecanoic acid Cypentadecanoic acid-dimethylamide C178115NO2 (285,47) calculation Value C71,53N12.36 N4.91 Measured value C71,65N12.19 N4.93 Example 5: 4-(13-hydroxytridecanoic acid) C-1-oxotridecyl)morpholine C□7H33NO8 (299,45) Calculated value C68, 19Hll, 11 N4.68 Measured value C68, 16Hll, 03 N4.74 Front page continuation (72) Inventor Nef, Günter Federal Republic of Germany D-1000 Berri 15 Markgraf Albrechtstrasse 4 (72) Inventor Kirsch, Geralt Federal Republic of Germany D-1000 Bells Lin 33 Lucius Strasse 6be
Claims (1)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19924214895 DE4214895A1 (en) | 1992-05-07 | 1992-05-07 | Process for the preparation of hydroxyalkane carboxamides |
| DE4214895.2 | 1992-05-07 | ||
| PCT/DE1993/000413 WO1993022278A1 (en) | 1992-05-07 | 1993-05-05 | Process for producing hydroxyalkane carboxylic acid amides |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH07506819A true JPH07506819A (en) | 1995-07-27 |
Family
ID=6458253
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP5518842A Pending JPH07506819A (en) | 1992-05-07 | 1993-05-05 | Process for producing hydroxyalkanecarboxylic acid amide |
Country Status (9)
| Country | Link |
|---|---|
| EP (1) | EP0639177A1 (en) |
| JP (1) | JPH07506819A (en) |
| AU (1) | AU4259493A (en) |
| CA (1) | CA2127292A1 (en) |
| DE (1) | DE4214895A1 (en) |
| FI (1) | FI945181A0 (en) |
| HU (1) | HUT68198A (en) |
| NO (1) | NO944238L (en) |
| WO (1) | WO1993022278A1 (en) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4420736C1 (en) * | 1994-06-15 | 1995-08-10 | Henkel Kgaa | New pseudo-ceramide cpds. |
| DE4427837A1 (en) * | 1994-08-05 | 1996-02-08 | Hoechst Ag | Process for the preparation of O-acylglycolic acid anilides |
| DE19525098A1 (en) * | 1995-07-10 | 1997-01-16 | Hoechst Ag | Process for the preparation of hydroxycarboxylic acid anilides |
| US7541489B2 (en) | 2004-06-30 | 2009-06-02 | Sabic Innovative Plastics Ip B.V. | Method of making halophthalic acids and halophthalic anhydrides |
| DE102008017213B4 (en) * | 2008-04-04 | 2012-08-09 | Clariant International Limited | Continuous process for the preparation of amides of aliphatic hydroxycarboxylic acids |
| WO2010108817A1 (en) | 2009-03-26 | 2010-09-30 | Basf Se | Method for producing n,n`-lactic acid dialkylamide using ionic liquids |
| WO2010108814A1 (en) | 2009-03-26 | 2010-09-30 | Basf Se | Method for producing n,n`-lactic acid dialkylamide under pressure |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB868556A (en) * | 1957-05-02 | 1961-05-17 | Hoechst Ag | Analeptically active ª--hydroxy-and ª--acyloxy-butyric acid alkyl-amides and a process for their manufacture |
| DE3905325A1 (en) * | 1989-02-17 | 1990-09-06 | Schering Ag | HYDROXYALKANCARBONE ACID DERIVATIVES, THEIR PREPARATION AND USE |
-
1992
- 1992-05-07 DE DE19924214895 patent/DE4214895A1/en not_active Withdrawn
-
1993
- 1993-05-05 EP EP93911742A patent/EP0639177A1/en not_active Withdrawn
- 1993-05-05 AU AU42594/93A patent/AU4259493A/en not_active Abandoned
- 1993-05-05 CA CA002127292A patent/CA2127292A1/en not_active Abandoned
- 1993-05-05 WO PCT/DE1993/000413 patent/WO1993022278A1/en not_active Application Discontinuation
- 1993-05-05 JP JP5518842A patent/JPH07506819A/en active Pending
- 1993-05-05 HU HU9401335A patent/HUT68198A/en unknown
-
1994
- 1994-11-03 FI FI945181A patent/FI945181A0/en not_active Application Discontinuation
- 1994-11-07 NO NO944238A patent/NO944238L/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DE4214895A1 (en) | 1993-11-11 |
| CA2127292A1 (en) | 1993-11-11 |
| FI945181A (en) | 1994-11-03 |
| FI945181A0 (en) | 1994-11-03 |
| EP0639177A1 (en) | 1995-02-22 |
| AU4259493A (en) | 1993-11-29 |
| NO944238D0 (en) | 1994-11-07 |
| WO1993022278A1 (en) | 1993-11-11 |
| HU9401335D0 (en) | 1994-08-29 |
| NO944238L (en) | 1994-11-07 |
| HUT68198A (en) | 1995-05-29 |
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