JPS5925375A - 1,3-dialkyl-2-halogeno-imidazolinium halogenide - Google Patents
1,3-dialkyl-2-halogeno-imidazolinium halogenideInfo
- Publication number
- JPS5925375A JPS5925375A JP13302582A JP13302582A JPS5925375A JP S5925375 A JPS5925375 A JP S5925375A JP 13302582 A JP13302582 A JP 13302582A JP 13302582 A JP13302582 A JP 13302582A JP S5925375 A JPS5925375 A JP S5925375A
- Authority
- JP
- Japan
- Prior art keywords
- dialkyl
- imidazolinium
- halogeno
- formula
- halogenide
- 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
Landscapes
- Compositions Of Macromolecular Compounds (AREA)
Abstract
Description
【発明の詳細な説明】
本発明は新規な１．３−ジアルキル−２−ハロゲノ−イ
ミダゾリニウム・ハレゲニド、（式中、Ｒ１及びＲ２は
低級アルキル基’ｌ Ｘはハロゲン原子を示す）
従来、アルシールとカルボン酸とからエステルを製造す
る方法としては種々の方法が知られており、その一つに
は縮汀剤全団用する方法があり、その縮合剤としても多
くのものにはエステル化反応によって得られるものが多
いことから、本発明者は、エステル化反応について鋭意
研究を行っていたところ、上記一般式（１）で表わされ
る化合物がエステル化反応の縮合剤として潰れているこ
とを見出し、不発明全完成した。DETAILED DESCRIPTION OF THE INVENTION The present invention provides a novel 1,3-dialkyl-2-halogeno-imidazolinium halegenide (wherein R1 and R2 are lower alkyl groups and X represents a halogen atom), Various methods are known for producing esters from Alsil and carboxylic acid, one of which is to use all the condensing agents; Since there are many products that can be obtained by the reaction, the present inventor conducted intensive research on the esterification reaction and discovered that the compound represented by the above general formula (1) can be used as a condensing agent for the esterification reaction. Heading, non-invention complete.
本発明化合物（１）は、例えば入手容易な溶剤として知
られている次の一般式（ＩＩ）（式中、ＲＩ及びＲ１は
前記した意味を有する）で表わされる１、３−ジアルキ
ル−２−イミダゾリジノンにハロゲン化剤全反応せしめ
ることにより製造される。The compound (1) of the present invention is, for example, a 1,3-dialkyl-2- It is produced by fully reacting imidazolidinone with a halogenating agent.
ここで使用されるハロゲン化剤としては、オキザリルク
ロライド、三ハロゲン化リン、五ハロゲン化リン、オキ
シハロゲン化リン、ホスゲン、トリクロロメチルクロロ
ホルメート等が挙げられる。反応は１，３−ジアルキル
−２−イミダゾリジノン又はハロゲン化剤の何れか一方
全四塩化炭素等の適当な溶媒にとかしておき、これに曲
方を少量ずつ添加し、更に室温ないし７０℃で数時χ間
〜士数時間反応させることによ゛つて行われる。Examples of the halogenating agent used here include oxalyl chloride, phosphorus trihalide, phosphorus pentahalide, phosphorus oxyhalide, phosgene, trichloromethyl chloroformate, and the like. The reaction is carried out by dissolving either the 1,3-dialkyl-2-imidazolidinone or the halogenating agent in a suitable solvent such as all-carbon tetrachloride, adding the compound little by little, and then heating at room temperature to 70°C. This is carried out by allowing the reaction to take place for several to several hours.
斯クシて得られる１、３−ジアルキル−２−ハロゲノ−
イミダゾリニウム・ハロゲニドは単離することもできる
が、単離することなく、その反応液？エステル化反応に
使用することもできる。1,3-dialkyl-2-halogeno- thus obtained
Imidazolinium halogenide can be isolated, but what about its reaction solution without isolation? It can also be used in esterification reactions.
本発明化合物（１）’に使用してエステル化反応を行う
には、アルコール（１）、カルボン９ＷＪ、１．３−ジ
アルキル−２−ハロゲノ−イミダゾリニウム・ハロゲ二
ド（１）の各１モルとピリジン、トリエチルアミン、ト
リブチルアミン等の塩基（Ｖ）２モルを混オロして室温
で反応させればよく、このとき反応は次式に従って進行
して、好収率でエステル（ロ）を与える。In order to carry out the esterification reaction using the compound (1)' of the present invention, each of alcohol (1), carvone 9WJ, and 1,3-dialkyl-2-halogeno-imidazolinium halogenide (1) is used. mol and 2 moles of a base (V) such as pyridine, triethylamine, tributylamine, etc. may be mixed together and reacted at room temperature. At this time, the reaction proceeds according to the following formula to give the ester (B) in a good yield. .
（１） （Ｖ） （１）
（Ｖ）（ＶＤ （Ｉ］）
（式中、Ｒ１はアルコール残基、Ｒ６はカルボン酸残基
、Ｂは塩基を示し、Ｒ１，Ｒ，及びＸは前記した意味を
有するＪ
次に実施例及び参考例を挙げて説明する。(1) (V) (1)
(V) (VD (I)) (In the formula, R1 is an alcohol residue, R6 is a carboxylic acid residue, B is a base, and R1, R, and X have the meanings described above.J) Next, Examples and This will be explained using a reference example.
実施例１゜
オキザリルクロライド２５２を四塩化炭素５１ ａｔに
静かし、これに１′、３−ジメチル−２−イミダゾリジ
ノン２６．９１に２０分を要して滴下し、更ｅこ６０℃
で５時間加熱して反応させた。反応液を室温筐で冷却１
２、析出した結晶ゲ戸取Ｌ 、四塩化炭素、Ｄ−ヘキサ
ノで順次洗浄後乾燥（７て１，３−ジメチル−２−クロ
ロ−イミダゾリニウム・クロライド２３１（収率６９チ
）を得た。Example 1 Oxalyl chloride 252 was stirred in 51 atm of carbon tetrachloride, added dropwise to 1',3-dimethyl-2-imidazolidinone 26.91 over 20 minutes, and further heated at 60°C.
The mixture was heated for 5 hours to react. Cool the reaction solution in a room temperature cabinet 1
2. The precipitated crystals were washed with L, carbon tetrachloride, and D-hexano in sequence and dried (1,3-dimethyl-2-chloro-imidazolinium chloride 231 (yield 69) was obtained in step 7). .
工Ｒ（ＫＢｒｌａｎ’ ： １６３０，１５４０，１
４１５，１３４０．１３００゜１２３０．１１４０．９
６０
ＩＱＭＲ（δ、ｐｐｍＸＣＤＣＩＩ ） ：３．３４
ｔ ｓ、６’Ｈ、−ＣＨ３Ｘ ２ ）４．３７ （ｓ、
４Ｈ，−ＯＨ，ＯＨ，−１参考例１゜
ε−グアニジノカプロン酸・メタンスルホン酸塩３０．
１ｒ、ｐ−ヒドロキシ安息香酸エチル２０．４Ｆ、ジク
ロルメタン１０（ｌｌｊの混合物中に、１．３−ジメチ
ル−２−クロロ−イミダゾリニウム・クロライド１８．
９ｒｉ加え、次いでピリジン１７．７ｆ全５分間で滴下
した。これを更に一夜攪拌］〜、析出した結晶を炉取し
、クロロホルムで洗浄した。涙液及び洗液を合し、減圧
下溶媒を留去し、水を加えて希釈した後、飽和炭酸水素
す） ＩＪウム水水酸液１５１中に攪拌下加えた。析出
晶を戸数し、水、アセトンで順次洗浄後乾燥して、Ｃ−
グアニジノカプロン酸・ｐ−エトキシカルボニルフェニ
ルエステルの炭酸塩２ｓ、２ｙ（収率６５．９％ｌ全得
た。Engineering R (KBrlan': 1630, 1540, 1
415,1340.1300゜1230.1140.9
60 IQMR (δ, ppmXCDCII): 3.34
t s, 6'H, -CH3X 2 )4.37 (s,
4H, -OH,OH, -1 Reference example 1゜ε-guanidinocaproic acid methanesulfonate 30.
In a mixture of 1r, ethyl p-hydroxybenzoate 20.4F, dichloromethane 10(llj), 1,3-dimethyl-2-chloro-imidazolinium chloride 18.
9ri was added, and then 17.7f of pyridine was added dropwise over a total of 5 minutes. This was further stirred overnight], and the precipitated crystals were collected in a furnace and washed with chloroform. The lachrymal fluid and washing fluid were combined, the solvent was distilled off under reduced pressure, water was added to dilute the mixture, and the mixture was added to saturated hydrogen carbonate solution 151 with stirring. Separate the precipitated crystals, wash them with water and acetone, and dry them to obtain C-
Carbonates of guanidinocaproic acid p-ethoxycarbonylphenyl ester 2s, 2y (yield 65.9%) were obtained.
以上 出願人 白鳥製薬株式会社 Ｃ−１ 弁理士 小 野 信 夫”、、’１ ［□′□ 、ｊ ′、１−；′・Ｌ）that's all Applicant: Shiratori Pharmaceutical Co., Ltd. C-1 Patent Attorney Nobuo Kono”,,’1 [□′□ ,j ′, 1-;′・L)
Claims (1)
ン原子金示す） で表わされる１、３−ジアルキル−２−ノ・ロゲノーイ
ミダゾリニウム・ノ・ロゲニド。 、？、１．３−ジメチルー２−クロロ−イミダゾリニウ
ム・クロライドである特ｌｆ′ｔｅｌ！求の範囲第１[Claims] 1. 1,3-dialkyl-2-logeno represented by the following general formula (1) (wherein R and R7 represent a lower alkyl group or a halogen atom) Imidazolinium norogenide. ,? , 1,3-dimethyl-2-chloro-imidazolinium chloride, lf'tel! Search range 1
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP13302582A JPS5925375A (en) | 1982-07-30 | 1982-07-30 | 1,3-dialkyl-2-halogeno-imidazolinium halogenide |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP13302582A JPS5925375A (en) | 1982-07-30 | 1982-07-30 | 1,3-dialkyl-2-halogeno-imidazolinium halogenide |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS5925375A true JPS5925375A (en) | 1984-02-09 |
Family
ID=15095033
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP13302582A Pending JPS5925375A (en) | 1982-07-30 | 1982-07-30 | 1,3-dialkyl-2-halogeno-imidazolinium halogenide |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5925375A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0751131A1 (en) * | 1995-06-20 | 1997-01-02 | MITSUI TOATSU CHEMICALS, Inc. | A process for preparing an acyl halide or sulfonyl halide |
| EP0895991A2 (en) * | 1997-08-06 | 1999-02-10 | Mitsui Chemicals, Inc. | Halogenating agent |
| US6127583A (en) * | 1998-04-07 | 2000-10-03 | Mitsui Chemicals, Inc. | Process for preparing acetylene derivative from a ketone compound |
-
1982
- 1982-07-30 JP JP13302582A patent/JPS5925375A/en active Pending
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0751131A1 (en) * | 1995-06-20 | 1997-01-02 | MITSUI TOATSU CHEMICALS, Inc. | A process for preparing an acyl halide or sulfonyl halide |
| EP0895991A2 (en) * | 1997-08-06 | 1999-02-10 | Mitsui Chemicals, Inc. | Halogenating agent |
| EP0895991A3 (en) * | 1997-08-06 | 2001-09-05 | Mitsui Chemicals, Inc. | Halogenating agent |
| US6329529B1 (en) | 1997-08-06 | 2001-12-11 | Mitsui Chemicals, Inc. | Nitrogen-based halogenating agents and process for preparing halogen-containing compounds |
| US6458990B1 (en) | 1997-08-06 | 2002-10-01 | Mitsui Chemicals, Inc. | Nitrogen-based halogenating agents and process for preparing halogen-containing compounds |
| US6632949B2 (en) | 1997-08-06 | 2003-10-14 | Mitsui Chemicals, Inc. | Halogenating agents |
| US6127583A (en) * | 1998-04-07 | 2000-10-03 | Mitsui Chemicals, Inc. | Process for preparing acetylene derivative from a ketone compound |
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