JPH0224824B2 - - Google Patents
Info
- Publication number
- JPH0224824B2 JPH0224824B2 JP1438181A JP1438181A JPH0224824B2 JP H0224824 B2 JPH0224824 B2 JP H0224824B2 JP 1438181 A JP1438181 A JP 1438181A JP 1438181 A JP1438181 A JP 1438181A JP H0224824 B2 JPH0224824 B2 JP H0224824B2
- Authority
- JP
- Japan
- Prior art keywords
- oxazolidones
- reaction
- lower alkyl
- alkyl
- group
- 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.)
- Expired
Links
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 15
- WDGCBNTXZHJTHJ-UHFFFAOYSA-N 2h-1,3-oxazol-2-id-4-one Chemical class O=C1CO[C-]=N1 WDGCBNTXZHJTHJ-UHFFFAOYSA-N 0.000 claims description 12
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 7
- 239000002904 solvent Substances 0.000 claims description 7
- 239000002202 Polyethylene glycol Substances 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 229920001223 polyethylene glycol Polymers 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 238000007126 N-alkylation reaction Methods 0.000 claims description 4
- 150000005215 alkyl ethers Chemical class 0.000 claims description 4
- 150000001350 alkyl halides Chemical class 0.000 claims description 4
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 claims description 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 description 21
- IZXIZTKNFFYFOF-UHFFFAOYSA-N 2-Oxazolidone Chemical compound O=C1NCCO1 IZXIZTKNFFYFOF-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 6
- 239000006227 byproduct Substances 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- VWIIJDNADIEEDB-UHFFFAOYSA-N 3-methyl-1,3-oxazolidin-2-one Chemical compound CN1CCOC1=O VWIIJDNADIEEDB-UHFFFAOYSA-N 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 3
- 229940050176 methyl chloride Drugs 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 150000001351 alkyl iodides Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 150000001649 bromium compounds Chemical class 0.000 description 1
- 150000004650 carbonic acid diesters Chemical class 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- NEHMKBQYUWJMIP-NJFSPNSNSA-N chloro(114C)methane Chemical compound [14CH3]Cl NEHMKBQYUWJMIP-NJFSPNSNSA-N 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000011437 continuous method Methods 0.000 description 1
- 238000006704 dehydrohalogenation reaction Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 150000004694 iodide salts Chemical class 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- -1 lithium or sodium Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000007069 methylation reaction Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000001766 physiological effect Effects 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
Landscapes
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Description
本発明はＮ−アルキル−２−オキサゾリドン類
の製造法に関し、更に詳しくは水酸化ナトリウム
又は水酸化カリウム存在下、ポリエチレングリコ
ールジ低級アルキルエーテル溶媒中にてハロゲン
化低級アルキルにより２−オキサゾリドン類を高
選択的、高収率にＮ−アルキル化し、工業的に有
利にＮ−アルキル−２−オキサゾリドン類を製造
する方法に関する。
Ｎ−アルキル−２−オキサゾリドンは、非プロ
トン性極性溶媒として、又大きな誘電率を持つこ
とから種々の用途を持ち、その誘導体には生理活
性を有するものもあり、最近注目される有用な化
合物群である。
Ｎ−アルキル−２−オキサゾリドン類の合成法
として、Ｎ−アルキルエタノールアミン誘導体に
炭酸ジエステルを反応せしめるホーマイヤ法が従
来から知られているが、２−オキサゾリドン類の
Ｎ−アルキル化は未確立の合成経路であつた。文
献中の２−オキサゾリドン類のＮ−アルキル化
は、まずアミン基の水素をリチウム、ナトリウム
等のアルカリ金属で金属化した後、ヨウ化アルキ
ルでアルキル化する方法で、工業的に利用するに
は２段反応で効率が悪く、高価なうえに危険性を
伴うアルカリ金属を用いる割には収率が低い等の
問題点のある製造法である（実許公開、昭52−
7959）。
本発明者らは、かかる問題点を克服すべく鋭意
研究し、アルカリ金属水酸化物による、２−オキ
サゾリドン類とハロゲン化低級アルキルの脱ハロ
ゲン化水素反応においては、溶媒としてポリエチ
レングリコールジ低級アルキルエーテルを使用す
ることにより本反応が高選択的、高収率で進行す
ることを発見し、本発明に至つた。
本発明の２−オキサゾリドン類は、一般式
（式中R1〜R4は水素原子又は炭素数１〜10の
直鎖又は側鎖を有するアルキル基、炭素数１から
４のアルキル基を有する又は有しないアリール基
又はアラルキル基のいずれかを示し、R1〜R4は
同種又は異種でも良い）で示される化合物であ
る。
本発明の水酸化ナトリウム及び又は水酸化カリ
ウムは、溶解することなく固型物のまま反応に供
すればよく、その量は自由であるが、高反応率を
実現せしめるためには、２−オキサゾリドン類に
対し当量以上が必要である。経済性を加味しての
好ましい範囲は２−オキサゾリドン類に対し、モ
ル比で1.0〜3.0であり特に1.1〜1.7が好ましい。
本発明のハロゲン化低級アルキルは、メチル、
エチル、ｎ−プロピル、ｎ−ブチルの各ヨウ化
物、臭化物、塩化物であり、液又は気体の状態で
反応に供すれば良く、その量は自由であるが、高
反応率を実現せしめるためには２−オキサゾリド
ン類に対し当量以上が必要である。経済性を加味
しての好ましい範囲は、２−オキサゾリドン類に
対し、モル比で1.0〜2.0であり、特に1.05〜1.5で
ある。
本発明において溶媒として使用するポリエチレ
ングリコールジ低級アルキルエーテルは２種以上
の混合物でも使用できる。低級アルキル基とし
て、炭素数１〜４の直鎖のものが好ましく、特に
ポリエチレングリコールジメチルエーテルが優れ
ている。高反応率を実現せしめるためには反応条
件下で２−オキサゾリドン類を完全に溶解させる
必要があり、溶媒量として、重量比にて２−オキ
サゾリドン類の６倍量が必要である。経済性を加
味しての溶媒量は６倍から20倍であり、特に７倍
から15倍が好ましい。
反応温度は20℃から150℃までの範囲で任意に
選ぶことができるが特に30〜100℃が好ましい。
反応は大気圧下で行ないうるが、加圧下で行なう
ことが好ましい。本発明の方法を工業的に実施す
る場合、十分な原料接触が可能であれば回分式又
は連続式のいずれも採用することができる。又、
反応後に生成物を分離するに当り、通常一般の分
離操作を適用することができる。例えば、Ｎ−メ
チル−２−オキサゾリドンでは反応終了後、反応
混合物から遠心分離又はフイルター過により副
生塩を除去し、引き続き分離された液を蒸留精
製することにより、目的とするＮ−メチル−２−
オキサゾリドンを容易に得ることができる。
以下本発明を実施例によつて説明する。
実施例 １
吹き込み管、温度計、圧力計、仕込口をそなえ
た1000ml電磁回転撹拌式オートクレーブに、２−
オキサゾリドン40ｇ（0.47モル）、水酸化ナトリ
ウム28ｇ（0.7モル）およびジエチレングリコー
ルジメチルエーテル400ｇを仕込み、35℃にて３
時間かけて塩化メチル24ｇ（0.48モル）をガス状
で導入反応せしめた。塩化メチル導入後95℃まで
昇温し４時間反応させた。反応液から副生塩を
別、液をガスクロマトグラフイーにて分析し
た。Ｎ−メチル−２−オキサゾリドンの収率は
99.9％であつた。
比較例 １
実施例１のジエチレングリコールジメチルエー
テルの代りにトルエン400ｇを仕込み、実施例１
と同様に反応せしめた。塩化メチルは5.5ｇ
（0.11モル）しか導入できなかつた。反応液から
副生塩を別すると目的物は副生塩中に分離され
た。ブチルアルコールにて抽出し抽出液をガスク
ロマトグラフイにて分析した。Ｎ−メチル−２−
オキサゾリドンの収率は22％であつた。
実施例１と較べ、ジエチレングリコールジメチ
ルエーテルの効果が大きいことが明らかである。
比較例 ２
実施例１の装置に２−オキサゾリドン40ｇ、金
属ナトリウム10.6ｇ（0.46モル）、トルエン400ｇ
を仕込み、100℃まで昇温反応後冷却し生成した
水素をパージした後、実施例１と同様に反応せし
めた。塩化メチルは5.7ｇしか導入できず、比較
例１と同様に処理し、分析した。Ｎ−メチル−２
−オキサゾリドンの収率は23％であつた。
実施例 ２〜４
実施例１と同様に、表−１に示す原料にて反応
を行なつた。
The present invention relates to a method for producing N-alkyl-2-oxazolidones, and more specifically, the present invention relates to a method for producing N-alkyl-2-oxazolidones, and more specifically to a method for producing 2-oxazolidones with a lower alkyl halide in a polyethylene glycol di-lower alkyl ether solvent in the presence of sodium hydroxide or potassium hydroxide. The present invention relates to a method for producing N-alkyl-2-oxazolidones in an industrially advantageous manner through selective, high-yield N-alkylation. N-alkyl-2-oxazolidones have various uses as aprotic polar solvents and have a large dielectric constant, and some of their derivatives have physiological activity, making them a useful group of compounds that have recently attracted attention. It is. As a method for synthesizing N-alkyl-2-oxazolidones, the Hohmeyer method, in which an N-alkylethanolamine derivative is reacted with a carbonic acid diester, has been known for a long time, but N-alkylation of 2-oxazolidones is an unestablished synthetic method. It was hot on the route. The N-alkylation of 2-oxazolidones in the literature is a method in which the hydrogen of the amine group is first metallized with an alkali metal such as lithium or sodium, and then alkylated with alkyl iodide. This production method has problems such as low efficiency due to the two-stage reaction, low yield considering the use of expensive and dangerous alkali metals (Jitsugoku Publication, 1972-
7959). The present inventors have conducted intensive research to overcome such problems, and have found that polyethylene glycol di-lower alkyl ether is used as a solvent in the dehydrohalogenation reaction of 2-oxazolidones and lower alkyl halides using an alkali metal hydroxide. The present inventors have discovered that this reaction can proceed with high selectivity and high yield by using this method, leading to the present invention. The 2-oxazolidones of the present invention have the general formula (In the formula, R 1 to R 4 represent either a hydrogen atom or an alkyl group having a linear or side chain having 1 to 10 carbon atoms, an aryl group having or not having an alkyl group having 1 to 4 carbon atoms, or an aralkyl group) and R 1 to R 4 may be the same or different. The sodium hydroxide and/or potassium hydroxide of the present invention may be used in the reaction as a solid without being dissolved, and the amount can be freely determined, but in order to achieve a high reaction rate, 2-oxazolidone An equivalent amount or more is required for the class. Taking economic efficiency into account, the preferred range is 1.0 to 3.0 in terms of molar ratio to the 2-oxazolidones, with 1.1 to 1.7 being particularly preferred. The halogenated lower alkyl of the present invention includes methyl,
These are iodides, bromides, and chlorides of ethyl, n-propyl, and n-butyl, and they can be used in the reaction in a liquid or gas state, and the amount can be freely determined, but in order to achieve a high reaction rate, is required in an amount equivalent to or more than the 2-oxazolidones. Taking economic efficiency into account, the preferred range is 1.0 to 2.0, particularly 1.05 to 1.5, in terms of molar ratio to the 2-oxazolidones. The polyethylene glycol di-lower alkyl ether used as a solvent in the present invention can also be used as a mixture of two or more. As the lower alkyl group, a linear one having 1 to 4 carbon atoms is preferable, and polyethylene glycol dimethyl ether is particularly excellent. In order to achieve a high reaction rate, it is necessary to completely dissolve the 2-oxazolidones under the reaction conditions, and the amount of solvent required is six times the amount of the 2-oxazolidones by weight. Taking economic efficiency into consideration, the amount of solvent is 6 to 20 times, preferably 7 to 15 times. The reaction temperature can be arbitrarily selected within the range of 20°C to 150°C, but 30 to 100°C is particularly preferred.
Although the reaction may be carried out under atmospheric pressure, it is preferable to carry out the reaction under elevated pressure. When the method of the present invention is carried out industrially, either a batch method or a continuous method can be employed as long as sufficient raw material contact is possible. or,
In separating the product after the reaction, common separation operations can be applied. For example, in the case of N-methyl-2-oxazolidone, after the reaction is completed, by-product salts are removed from the reaction mixture by centrifugation or filtering, and the separated liquid is subsequently purified by distillation to obtain the desired N-methyl-2-oxazolidone. −
Oxazolidone can be easily obtained. The present invention will be explained below with reference to Examples. Example 1 2-
40 g (0.47 mol) of oxazolidone, 28 g (0.7 mol) of sodium hydroxide and 400 g of diethylene glycol dimethyl ether were charged, and
24 g (0.48 mol) of methyl chloride was introduced in gaseous form over a period of time to cause a reaction. After the introduction of methyl chloride, the temperature was raised to 95°C and the reaction was carried out for 4 hours. By-product salts were separated from the reaction solution, and the solution was analyzed by gas chromatography. The yield of N-methyl-2-oxazolidone is
It was 99.9%. Comparative Example 1 400g of toluene was added in place of diethylene glycol dimethyl ether in Example 1, and Example 1
I reacted in the same way. Methyl chloride is 5.5g
(0.11 mol) could be introduced. When the by-product salt was separated from the reaction solution, the target product was separated into the by-product salt. It was extracted with butyl alcohol and the extract was analyzed by gas chromatography. N-methyl-2-
The yield of oxazolidone was 22%. Compared to Example 1, it is clear that the effect of diethylene glycol dimethyl ether is greater. Comparative Example 2 40 g of 2-oxazolidone, 10.6 g (0.46 mol) of sodium metal, and 400 g of toluene were added to the apparatus of Example 1.
was charged, the temperature was raised to 100°C, the reaction was cooled and the generated hydrogen was purged, and then the reaction was carried out in the same manner as in Example 1. Only 5.7 g of methyl chloride could be introduced, and it was treated and analyzed in the same manner as in Comparative Example 1. N-methyl-2
-The yield of oxazolidone was 23%. Examples 2 to 4 In the same manner as in Example 1, reactions were carried out using the raw materials shown in Table 1.
【表】
ハロゲン化低級アルキルとして、炭素数１から
４の低級アルキル基のヨウ化物、臭化物又は塩化
物が使用でき、アルカリ金属水酸化物として水酸
化ナトリウムおよび又は水酸化カリウムが使用で
きることが分る。
実施例５及び６
実施例１と同様に表−２に示す原料にて反応を
行なつた。[Table] It can be seen that the iodide, bromide or chloride of a lower alkyl group having 1 to 4 carbon atoms can be used as the lower alkyl halide, and sodium hydroxide and/or potassium hydroxide can be used as the alkali metal hydroxide. . Examples 5 and 6 Reactions were carried out in the same manner as in Example 1 using the raw materials shown in Table 2.
【表】
２−オキサゾリドンの４，５位の誘導基にかか
わらず、良好なメチル化反応が進行していること
が分る。[Table] It can be seen that the methylation reaction proceeded favorably regardless of the inducing groups at the 4 and 5 positions of 2-oxazolidone.
Claims (1)
存在下、ハロゲン化低級アルキルにて、一般式 （式中、R1〜R4は水素原子、炭素数１から10
の直鎖又は側鎖を持つアルキル基、又は炭素数１
から４のアルキル基を有する又は有しないアリー
ル基又はアラルキル基のいずれかを示し、R1〜
R4は同種又は異種でも良い）で表わされる２−
オキサゾリドン類のＮ−アルキル化に際し、ポリ
エチレングリコールジ低級アルキルエーテルを溶
媒として用いることを特徴とするＮ−アルキル−
２−オキサゾリドン類の製造法。 ２ 溶媒がポリエチレングリコールジメチルエー
テルである特許請求の範囲第１項記載の方法。[Claims] 1. In the presence of sodium hydroxide and/or potassium hydroxide, at a lower alkyl halide, the general formula (In the formula, R 1 to R 4 are hydrogen atoms, carbon atoms 1 to 10
an alkyl group with a straight chain or side chain, or a carbon number of 1
represents either an aryl group or an aralkyl group with or without an alkyl group of 4, and R 1 to
R 4 may be of the same type or different types) 2-
N-alkyl-, characterized in that polyethylene glycol di-lower alkyl ether is used as a solvent during N-alkylation of oxazolidones.
Method for producing 2-oxazolidones. 2. The method according to claim 1, wherein the solvent is polyethylene glycol dimethyl ether.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1438181A JPS57130978A (en) | 1981-02-04 | 1981-02-04 | Preparation of n-alkyl-2-oxazolidone compound |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1438181A JPS57130978A (en) | 1981-02-04 | 1981-02-04 | Preparation of n-alkyl-2-oxazolidone compound |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS57130978A JPS57130978A (en) | 1982-08-13 |
| JPH0224824B2 true JPH0224824B2 (en) | 1990-05-30 |
Family
ID=11859460
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP1438181A Granted JPS57130978A (en) | 1981-02-04 | 1981-02-04 | Preparation of n-alkyl-2-oxazolidone compound |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS57130978A (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2023515360A (en) * | 2020-02-14 | 2023-04-13 | アンガス ケミカル カンパニー | Low toxicity NMP substitute and method for its preparation |
-
1981
- 1981-02-04 JP JP1438181A patent/JPS57130978A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS57130978A (en) | 1982-08-13 |
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