JPS6067471A - Tetrahydro-3-methyl-5-isopropyl-4h-1,3,5-oxadiazin-4-one - Google Patents
Tetrahydro-3-methyl-5-isopropyl-4h-1,3,5-oxadiazin-4-oneInfo
- Publication number
- JPS6067471A JPS6067471A JP58175832A JP17583283A JPS6067471A JP S6067471 A JPS6067471 A JP S6067471A JP 58175832 A JP58175832 A JP 58175832A JP 17583283 A JP17583283 A JP 17583283A JP S6067471 A JPS6067471 A JP S6067471A
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- compound
- isopropylurea
- formula
- tetrahydro
- 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
- SEEGKYBTVVQFER-UHFFFAOYSA-N 3-methyl-5-propan-2-yl-1,3,5-oxadiazinan-4-one Chemical compound CC(C)N1COCN(C)C1=O SEEGKYBTVVQFER-UHFFFAOYSA-N 0.000 title claims description 3
- 150000001875 compounds Chemical class 0.000 abstract description 18
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 abstract description 17
- YLFYUSNPIHLTBP-UHFFFAOYSA-N 1-methyl-3-propan-2-ylurea Chemical compound CNC(=O)NC(C)C YLFYUSNPIHLTBP-UHFFFAOYSA-N 0.000 abstract description 8
- 239000002904 solvent Substances 0.000 abstract description 7
- 239000005486 organic electrolyte Substances 0.000 abstract description 4
- 239000007788 liquid Substances 0.000 abstract description 3
- 239000012530 fluid Substances 0.000 abstract description 2
- 239000000463 material Substances 0.000 abstract description 2
- 238000007086 side reaction Methods 0.000 abstract description 2
- 230000001747 exhibiting effect Effects 0.000 abstract 1
- 239000012429 reaction media Substances 0.000 abstract 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 150000005063 oxadiazines Chemical class 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000004202 carbamide Substances 0.000 description 3
- 239000012024 dehydrating agents Substances 0.000 description 3
- 230000018044 dehydration Effects 0.000 description 3
- 238000006297 dehydration reaction Methods 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 229930040373 Paraformaldehyde Natural products 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 229920002866 paraformaldehyde Polymers 0.000 description 2
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000004566 IR spectroscopy Methods 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000010533 azeotropic distillation Methods 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000012159 carrier gas Substances 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- JKWMSGQKBLHBQQ-UHFFFAOYSA-N diboron trioxide Chemical compound O=BOB=O JKWMSGQKBLHBQQ-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 239000008098 formaldehyde solution Substances 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 230000010287 polarization Effects 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- -1 urea compound Chemical class 0.000 description 1
- 210000002700 urine Anatomy 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Landscapes
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
Abstract
Description
【発明の詳細な説明】
本発明は新規なオキサジアジン誘導体およびその製法に
関する。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to novel oxadiazine derivatives and methods for their production.
従来オキサジアジン誘導体は染色助剤等に有用であり、
種々の化合物が知られているが、２個のＮ−置換基がそ
れぞれ異なったアルキル基を有し、かつそのＮ−置換ア
ルキル基の少なくとも一個が分岐鎖を有する化合物は知
られていない。Conventionally, oxadiazine derivatives are useful as dyeing aids, etc.
Various compounds are known, but no compound is known in which two N-substituted groups have different alkyl groups and at least one of the N-substituted alkyl groups has a branched chain.
本発明者らは種々のオキサジアジン誘導体の製法および
生成物の物性を検討するうち、２個のＮ−置換基がそれ
ぞれ興なったアルキル基を有し、かつそのＮ−置換アル
キル基の少なくとも一個か分岐鎖を有する化合物、就中
、テトラヒドロ−３−メチル−５−イソプロピル−４Ｈ
−１，３，５−オキサジアジン−４−オンが常温で液状
であり、高い誘電率を有することから有機電解液、高速
インキシェツト用媒体およびある特定電圧範囲において
残留分極を示すためその分野での用途等に有用であるこ
とを見出した。The present inventors investigated various methods for producing oxadiazine derivatives and the physical properties of the products, and found that two N-substituents each have an alkyl group, and at least one of the Compounds with branched chains, especially tetrahydro-3-methyl-5-isopropyl-4H
-1,3,5-Oxadiazin-4-one is liquid at room temperature and has a high dielectric constant, so it is used as an organic electrolyte, a medium for high-speed inkjet, and because it exhibits residual polarization in a certain voltage range, it is used in those fields. We have found that it is useful for
即ち、本発明は式：
で示される化合物、即ちテトラヒドロ−３−メチル−５
−イソプロピル−４８−−１，３，５−オキサジアジン
−４−オンおよびその製法を提供する。That is, the present invention provides a compound represented by the formula: Tetrahydro-3-methyl-5
-isopropyl-48--1,3,5-oxadiazin-4-one and a method for producing the same.
一般的なオキサジアジン類の製造方法はＪ 、 Ｏｒｇ
。A general method for producing oxadiazines is described by J. Org.
.
Ｃｈｅｍ、２８．．１８７’６〜７（１９６３）、Ｂｕ
ｌｌ、 Ｃｂｅｍ、 Ｓｏｃ、 Ｊａｐａｎ １１ 、
２４８〜’２６１（１９３６）、Ｊ 、 Ｏｒｇ、Ｃｈ
ｅｍ、 ２９． ２７７７〜８（１９６４） 等に記載
されている。しかしながら従来のジアルキル尿素とパラ
ホルムアルデヒドを脱水縮合する反応（Ｊ、Ｏｒｇ、
Ｃｈｅｍ、 ２９．２７７７〜８ （１９６４））では
未反応のジアルキル尿素が残存したりジアルキル尿素の
ジメチロール化物が残存する。また反応か完全に行なわ
れなかったために生ずる種々の副生物等が生成し、これ
は蒸溜等の通常の精製手段で分離除去することは困難で
ある。また前述の有機電解質として使用するにはかなり
の高純度の化合物が要請される。Chem, 28. ．． 187'6-7 (1963), Bu
ll, Cbem, Soc, Japan 11,
248-'261 (1936), J, Org, Ch.
em, 29. 2777-8 (1964), etc. However, the conventional dehydration condensation reaction of dialkylurea and paraformaldehyde (J, Org,
Chem, 29.2777-8 (1964)), unreacted dialkylurea or dimethylolated dialkylurea remains. In addition, various by-products are generated due to incomplete reaction, and these are difficult to separate and remove by ordinary purification means such as distillation. Further, use as the above-mentioned organic electrolyte requires a compound of considerably high purity.
本発明者らは上記の問題を解決するためジアルキル尿素
（本発明では１−メチル−３−イソプロピル尿素を用い
た）とパラホルムアルデヒドとを、酸触媒の存在下に反
応させてジメチロール化を完結させ、次いでベンゼン等
の溶剤を用いて水分を共沸により除去し、その後、更に
脱水剤を加えて脱水し、ジメチロール化尿素を完全に脱
水環化させることにより、高純度のオキサジアジン誘導
体を得ることに成功した。In order to solve the above problem, the present inventors completed dimethylolation by reacting dialkylurea (1-methyl-3-isopropylurea was used in the present invention) and paraformaldehyde in the presence of an acid catalyst. Next, water is removed azeotropically using a solvent such as benzene, and then a dehydrating agent is added for dehydration to completely dehydrate and cyclize the dimethylolated urea, thereby obtaining a highly pure oxadiazine derivative. Successful.
即ち、本発明は１−メチル−３−イソプロピル尿素とホ
ルムアルデヒドを反応させて、１−メチル−３−イソプ
ロピル尿素のジメチロール化物を得、これを脱水環化さ
せることを特徴とする式：で示されるテトラヒドロ−３
−メチル−５−インプロピル−４Ｈ−１，３，５−オキ
サジアジン−４−オンの製法を提供する。That is, the present invention is characterized by reacting 1-methyl-3-isopropylurea with formaldehyde to obtain a dimethylolated product of 1-methyl-3-isopropylurea, and cyclizing this by dehydration. Tetrahydro-3
-Methyl-5-inpropyl-4H-1,3,5-oxadiazin-4-one is provided.
１−メチル−３−イソプロピル尿素とホルムアルデヒド
の反応は１−メチル−３−イソプロピル尿素を通常ホル
ムアルデヒド水溶液、例えば３５％水溶液に溶解し、酸
性触媒、例えば塩酸、硫酸、リン酸、パラトルエンスル
ホン酸ｌ及び／あるいはこれらの酸性塩等を加え、室温
で１〜３時間攪拌することにより行うう。この反応によ
り１−メチル−３−イソプロピル尿素のジメチロール化
物か得られる。ホルムアルデヒドは１−メチル−３−イ
ソプロピル尿素１モルに対し２モル以上、好ましくは２
．０５〜２．５モル用いる。酸性触媒は原料尿素化合物
の０．５重量％程度用いる。反応が完了した後、例えば
ベンゼン、トルエン、キシレン等共沸溶剤を反応系中に
存在する水を共沸により除去するに十分な量加え、加熱
共沸により、水分のほぼ全量を除去する。最後に反応を
完全にするためにジメチロール化物の共沸溶剤溶液に適
当な脱水剤、例えばＰ２Ｏ３、無水硼酸等をジメチロー
ル化物１００重量部に対し５〜１０重量部加え還流加熱
する。脱水剤は適当な手段、例えば沖過、遠心分離等に
より除去し、共沸溶剤を溜去することにより、本発明化
合物を得ることができる。The reaction between 1-methyl-3-isopropylurea and formaldehyde is carried out by dissolving 1-methyl-3-isopropylurea in an aqueous formaldehyde solution, such as a 35% aqueous solution, and using an acidic catalyst such as hydrochloric acid, sulfuric acid, phosphoric acid, or para-toluenesulfonic acid. and/or by adding these acid salts, etc., and stirring at room temperature for 1 to 3 hours. This reaction yields a dimethylolated product of 1-methyl-3-isopropylurea. Formaldehyde is used in an amount of 2 mol or more, preferably 2 mol or more per 1 mol of 1-methyl-3-isopropylurea.
．． 05 to 2.5 mol is used. The acidic catalyst is used in an amount of about 0.5% by weight of the raw material urea compound. After the reaction is completed, an azeotropic solvent such as benzene, toluene, or xylene is added in an amount sufficient to azeotropically remove the water present in the reaction system, and almost all of the water is removed by heating azeotropically. Finally, in order to complete the reaction, 5 to 10 parts by weight of a suitable dehydrating agent, such as P2O3, boric anhydride, etc., are added to the azeotropic solvent solution of the dimethylol compound per 100 parts by weight of the dimethylol compound and heated under reflux. The compound of the present invention can be obtained by removing the dehydrating agent by an appropriate means such as filtration or centrifugation, and distilling off the azeotropic solvent.
本発明化合物は水に可溶性の液状化合物であり、誘電率
の高い溶媒として、有機電解質、高速イン機能流体とし
て種々の分野に使用できる。The compound of the present invention is a liquid compound soluble in water, and can be used in various fields as a solvent with a high dielectric constant, as an organic electrolyte, and as a high-speed in-function fluid.
また本発明方法によれば副反応が少なく、簡単な操作で
純度の高い化合物を高収率で得ることができる。Furthermore, according to the method of the present invention, there are few side reactions, and a highly pure compound can be obtained in high yield with simple operations.
以下、実施例をあげて説明する。Examples will be described below.
実施例
１−メチル−３−イソプロピル尿ｉ１１６ｇ（１モル）
を３５％ホルマリン溶液１８８ｇ（２，２モル）に溶解
し、これに濃塩酸０．５ｍｌを添加し、室温で１時間攪
拌する。原料尿素の消失をＴ Ｌ ＣでＷｉＢＥ後、こ
れにベンゼン２００ｎｉｌ！を加え、ディーンスターク
の蒸溜器を付し、生成水分および原料ホルマリン溶液の
水分を共沸により糸夕目こ除去する。水分をほぼ除去し
た後、五酸化りん約２０ｇを添加し、１時間還流加熱し
、環化反応を完結させる。ＧＬＣによりジメチロール化
物の消失を６ｍｇ忍後、反応液を今加し、次いで五酸化
りんをρ過により除き、無水炭酸カリで中和する。更に
硫酸マグネシウムで乾燥し、ρ過後ベンゼンを、溜去＋
７−ｅ 初ｕｒｎ Ａ、こ０Ｑ ’／” ／ １Ｑ
ＹＪ＋ ％ Ｘｈ 八？、 ４ｍ Ｔｒ＋ｙした。収量
１４．５ ｇ （収率９１．８％）であった。Example 1 - Methyl-3-isopropyl urine i 116 g (1 mol)
was dissolved in 188 g (2.2 mol) of 35% formalin solution, 0.5 ml of concentrated hydrochloric acid was added thereto, and the mixture was stirred at room temperature for 1 hour. After WiBE with TLC to eliminate the raw material urea, add 200 nil of benzene to it! is added, and a Dean-Stark distiller is attached to remove the produced water and the water in the raw material formalin solution by azeotropic distillation. After almost all moisture has been removed, about 20 g of phosphorus pentoxide is added and heated under reflux for 1 hour to complete the cyclization reaction. After 6 mg of the dimethylol compound had disappeared by GLC, the reaction solution was added, and then phosphorus pentoxide was removed by filtration and neutralized with anhydrous potassium carbonate. Furthermore, it was dried with magnesium sulfate, and after passing ρ, the benzene was distilled off.
7-e First urn A, this 0Q '/" / 1Q
YJ+ % Xh 8? , 4m Tr+y. The yield was 14.5 g (yield 91.8%).
生成物の物理特数を表−１に、ガスクロマトグラム、赤
外吸収スペクトルおよびＮＭＲのチャート（基準ＴＭＳ
、溶剤ＣＣＩ！４、濃度〜２０％）を゛ それぞれ第１
図、第２図および第３図に示す。The physical properties of the product are shown in Table 1, gas chromatogram, infrared absorption spectrum, and NMR chart (standard TMS
, Solvent CCI! 4. Concentration ~ 20%) respectively 1st
2 and 3.
ガスクロマトグラフィーの測定条件は以下の通りである
。The measurement conditions for gas chromatography are as follows.
検出器： ＦＩＤ
カラム： ステンレス製、長さ１ｍ、充填剤Ｅ−３Ｑ
キャリヤーガス 二 Ｎ２：０．８に９／ｃＪインジ工
クシヨン温度：２２０’Ｃ
展開温度 ： １６０℃
チャート送り速度 ： ５隔／分
表−１Detector: FID Column: Stainless steel, length 1m, packing material E-3Q, carrier gas 2N2: 9/cJ to 0.8 Injection temperature: 220'C Developing temperature: 160'C Chart feed rate: 5 intervals/ Table-1
第１図は本発明化合物のガスクロマトグラム、第２図は
本発明化合物の赤外分光分析チャート、第３図は本発明
化合物のＮＭＲチャート、をそれぞれ示す。
第１図
第３図
＋０．０ ９．０ ８．０ ７．０ ６．０ＭＳFIG. 1 shows a gas chromatogram of the compound of the present invention, FIG. 2 shows an infrared spectroscopy chart of the compound of the present invention, and FIG. 3 shows an NMR chart of the compound of the present invention. Figure 1 Figure 3 +0.0 9.0 8.0 7.0 6.0MS
Claims (1)
ル−４Ｈ−１，３，５−オキサジアジン−４−オン。Tetrahydro-3-methyl-5-isopropyl-4H-1,3,5-oxadiazin-4-one.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP58175832A JPS6067471A (en) | 1983-09-22 | 1983-09-22 | Tetrahydro-3-methyl-5-isopropyl-4h-1,3,5-oxadiazin-4-one |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP58175832A JPS6067471A (en) | 1983-09-22 | 1983-09-22 | Tetrahydro-3-methyl-5-isopropyl-4h-1,3,5-oxadiazin-4-one |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS6067471A true JPS6067471A (en) | 1985-04-17 |
Family
ID=16002993
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP58175832A Pending JPS6067471A (en) | 1983-09-22 | 1983-09-22 | Tetrahydro-3-methyl-5-isopropyl-4h-1,3,5-oxadiazin-4-one |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6067471A (en) |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5792064A (en) * | 1980-11-28 | 1982-06-08 | Fuji Photo Film Co Ltd | Aqueous ink for ink jet print |
-
1983
- 1983-09-22 JP JP58175832A patent/JPS6067471A/en active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5792064A (en) * | 1980-11-28 | 1982-06-08 | Fuji Photo Film Co Ltd | Aqueous ink for ink jet print |
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