JPH0739402B2 - Method for producing aminotriazine derivative - Google Patents
Method for producing aminotriazine derivativeInfo
- Publication number
- JPH0739402B2 JPH0739402B2 JP63052227A JP5222788A JPH0739402B2 JP H0739402 B2 JPH0739402 B2 JP H0739402B2 JP 63052227 A JP63052227 A JP 63052227A JP 5222788 A JP5222788 A JP 5222788A JP H0739402 B2 JPH0739402 B2 JP H0739402B2
- Authority
- JP
- Japan
- Prior art keywords
- reaction
- formamide
- disubstituted
- producing
- amino
- 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 - Lifetime
Links
Description
【発明の詳細な説明】 〔技術分野〕 本発明は無置換または一置換ホルムアミドと二置換シア
ナミドとの反応によりアミノ−1,3,5−トリアジン化合
物を製造する方法に関するものである。Description: TECHNICAL FIELD The present invention relates to a method for producing an amino-1,3,5-triazine compound by reacting an unsubstituted or monosubstituted formamide with a disubstituted cyanamide.
アミノ−1,3,5−トリアジン化合物の合成は、メラミン
などの場合を除き、通常塩化シアヌルとアミン類を原料
として合成されることが知られている。このようにして
得られたアミノ−1,3,5−トリアジン化合物は農薬、医
薬、染料などに多く使用されている。It is known that the amino-1,3,5-triazine compound is usually synthesized using cyanuric chloride and amines as raw materials, except for the case of melamine. The amino-1,3,5-triazine compound thus obtained is widely used for agricultural chemicals, pharmaceuticals, dyes and the like.
しかし、この反応においては、原料の塩化シアヌルが吸
湿して脱塩酸分解を生じ易く、またアミン類との置換反
応によっても塩酸が生成し、反応の後処理を必要である
上、2,4,6位に入るアミノ基が同一でない場合には、反
応条件を変え、異なったアミンを使用して逐次置換を行
うため、多数の工程を必要とするという欠点があった。However, in this reaction, cyanuric chloride as a raw material absorbs moisture and easily undergoes dehydrochlorination decomposition, and hydrochloric acid is also generated by the substitution reaction with amines, and after-treatment of the reaction is required, and 2,4, If the amino groups at the 6-positions are not the same, the reaction conditions are changed, and different amines are used to perform sequential substitution, which has the drawback of requiring a large number of steps.
本発明は、アミノ−1,3,5−トリアジン化合物の合成に
見られる前記欠点を有しない新反応を提供するものであ
る。The present invention provides a new reaction which does not have the above-mentioned drawbacks found in the synthesis of amino-1,3,5-triazine compounds.
本発明者等は、アミノ−1,3,5−トリアジン化合物に関
して、比較的簡単な構造を有し、安価であり、且つ安定
な化合物を原料とし、前記欠点を有しない合成法につい
て種々検討した結果、ホルムアミドと二置換シアナミド
とを1000kg/cm2〜9000kg/cm2の圧力下で反応させると、
その２位にホルムアミドのアミノ基、4,6位にシアナミ
ドの二置換アミノ基を有する1,3,5−トリアジン化合物
が収率良く得られることを見出した。The present inventors have made various studies on amino-1,3,5-triazine compounds, which have relatively simple structures, are inexpensive, and are stable compounds, and have various synthetic methods that do not have the above-mentioned drawbacks. a result, when the reaction of formamide with disubstituted cyanamide under a pressure of 1000kg / cm 2 ~9000kg / cm 2 ,
It was found that a 1,3,5-triazine compound having a formamide amino group at the 2-position and a cyanamide disubstituted amino group at the 4- and 6-positions can be obtained in good yield.
すなわち、本発明においては、ホルムアミド１分子と二
置換シアナミド３分子からアミノ−1,3,5−トリアジン
１分子と、二置換シアナミドの二置換アミノ基を有する
二置換ホルムアミド１分子とが生成する。この副生する
二置換シアナミドは、固体生成物のアミノ−1,3,5−ト
リアジンの量が増加する反応終了時に溶媒として作用す
るため、特に反応系に溶媒を添加しないですむという利
点であるばかりでなく、この様な二置換ホルムアミドを
目的物とする新合成法としても有用である。 That is, in the present invention, 1 molecule of amino-1,3,5-triazine and 1 molecule of disubstituted formamide having a disubstituted amino group of disubstituted cyanamide are produced from 1 molecule of formamide and 3 molecules of disubstituted cyanamide. This by-produced di-substituted cyanamide acts as a solvent at the end of the reaction when the amount of amino-1,3,5-triazine of the solid product increases, and is particularly advantageous in that no solvent is added to the reaction system. Not only is it useful as a new synthetic method for such disubstituted formamide.
本発明において使用するホルムアミドは、無置換のホル
ムアミドの他、Ｎ−フェニルホルムアミド、Ｎ−ベンジ
ルホルムアミド、Ｎ−メチルホルムアミドなどの一置換
ホルムアミドを用いることができる。一方、二置換シア
ナミドとしては、ジメチルシアナミド、ジエチルシアナ
ミドなどの他１−ピペリジンカルボニトリル、１−ピロ
ジンカルボニトリル、１−モリホリンカルボニトリルな
どの環状シアナミドが含まれる。The formamide used in the present invention may be an unsubstituted formamide or a monosubstituted formamide such as N-phenylformamide, N-benzylformamide or N-methylformamide. On the other hand, examples of the disubstituted cyanamide include dimethylcyanamide, diethylcyanamide, and other cyclic cyanamides such as 1-piperidinecarbonitrile, 1-pyrazinecarbonitrile, and 1-morpholinecarbonitrile.
本発明の反応は加圧下で行われ、高圧ほど望ましいが、
一般的には1000〜9000kg/cm2の範囲で選択される。また
反応温度は通常50〜250℃の範囲で選択される。本発明
においては特に反応促進剤を用いる必要はない。また、
溶媒も必要としないが、二置換ホルムアミドなどの反応
に不活性な化合物を溶媒として使用しても問題はない。Although the reaction of the present invention is carried out under pressure, higher pressures are more desirable,
Generally, it is selected in the range of 1000 to 9000 kg / cm 2 . The reaction temperature is usually selected in the range of 50 to 250 ° C. In the present invention, it is not necessary to use a reaction accelerator. Also,
No solvent is required, but there is no problem if a compound inert to the reaction such as disubstituted formamide is used as a solvent.
次に本発明を実施例によりさらに詳細に説明する。 Next, the present invention will be described in more detail with reference to Examples.
なお、各実施例中に示す部は重量部を表わし、また、収
率に関する％は二置換シアナミドに関する理論収率であ
る。In addition, the part shown in each Example represents a weight part, and% relating to the yield is the theoretical yield concerning the disubstituted cyanamide.
実施例１ 3.4部のホルムアミドと24.7部の１−ピペリジンカルボ
ニトリル（モル比1:3）とをモフロンカプセル中に封入
し、高圧反応管に収納して約3000kg/cm2に加圧した後、
反応管を外熱して内部温度を160℃に昇温し、さらに圧
力を加えて4000kg/cm2とし20時間保持した。20時間経過
後、反応管を常温近くまで冷却した上で圧力を常圧と
し、カプセルを取り出して開封した。内容物をイソプロ
ピルエーテルで洗い出し、結晶状の固体生成物を分離
し、メタノールまたはイソプロピルエーテルからの再結
晶により２−アミノ−4,6−ジ（１−ピペリジン）−1,
3,5−トリアジン11.7部（収率60％）が得られた。Example 1 3.4 parts of formamide and 24.7 parts of 1-piperidinecarbonitrile (molar ratio 1: 3) were encapsulated in a moflon capsule, housed in a high pressure reaction tube and pressurized to about 3000 kg / cm 2. ,
The reaction tube was externally heated to raise the internal temperature to 160 ° C., and further pressure was applied to 4000 kg / cm 2 and the temperature was maintained for 20 hours. After 20 hours, the reaction tube was cooled to near room temperature, the pressure was adjusted to normal pressure, and the capsule was taken out and opened. The contents were washed out with isopropyl ether, the crystalline solid product was separated and recrystallized from methanol or isopropyl ether to give 2-amino-4,6-di (1-piperidine) -1,
11.7 parts (yield 60%) of 3,5-triazine were obtained.
実施例２〜16 実施例１と同じ手法で、原料混合モル比1:3、反応圧力4
000kg/cm2、反応温度160℃、反応時間20時間の条件で下
記のホルムアミドと二置換シアナミドとの15種の組合せ
の反応を行い、得られた15種のアミノトリアジンの収率
を表示した。Examples 2 to 16 In the same manner as in Example 1, the raw material mixing molar ratio was 1: 3, and the reaction pressure was 4
The following 15 types of combinations of formamide and disubstituted cyanamide were carried out under the conditions of 000 kg / cm 2 , reaction temperature of 160 ° C., and reaction time of 20 hours, and the yields of 15 types of aminotriazine obtained were displayed.
Claims (1)
は水素原子である。）で表わされるホルムアミドと 一般式 （式中R2、R3はアルキル基であり、さらにR2とR3が結合
した環状構造を有するものを含む。）で表わされる二置
換シアナミドとを1000kg/cm2〜9000kg/cm2の高圧下で反
応させることを特徴とする 一般式 （式中R1、R2、R3は前記と同じ）で表わされる1,3,5−
トリアジンの製造方法。1. A formamide represented by the general formula HCONHR 1 (wherein R 1 is an alkyl group, an aryl group, an aralkyl group or a hydrogen atom) and the general formula (In the formula, R 2 and R 3 are alkyl groups, and further include those having a cyclic structure in which R 2 and R 3 are bonded.) With a disubstituted cyanamide of 1000 kg / cm 2 to 9000 kg / cm 2 . General formula characterized by reacting under high pressure (Wherein R 1 , R 2 and R 3 are the same as above), 1,3,5-
Method for producing triazine.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP63052227A JPH0739402B2 (en) | 1988-03-04 | 1988-03-04 | Method for producing aminotriazine derivative |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP63052227A JPH0739402B2 (en) | 1988-03-04 | 1988-03-04 | Method for producing aminotriazine derivative |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH01226879A JPH01226879A (en) | 1989-09-11 |
| JPH0739402B2 true JPH0739402B2 (en) | 1995-05-01 |
Family
ID=12908855
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP63052227A Expired - Lifetime JPH0739402B2 (en) | 1988-03-04 | 1988-03-04 | Method for producing aminotriazine derivative |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0739402B2 (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2197858B1 (en) * | 2007-08-31 | 2014-07-02 | HanAll Biopharma Co., Ltd. | 1,3,5-triazine-2,4,6-triamine compound or pharmaceutical acceptable salt thereof, and pharmaceutical composition comprising the same |
-
1988
- 1988-03-04 JP JP63052227A patent/JPH0739402B2/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| JPH01226879A (en) | 1989-09-11 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EXPY | Cancellation because of completion of term |