JPH04169575A - Production of 6-imino-1,3,5-trisubstituted-1,3,5-perhydrotriazine-2,4-dithione derivative - Google Patents
Production of 6-imino-1,3,5-trisubstituted-1,3,5-perhydrotriazine-2,4-dithione derivativeInfo
- Publication number
- JPH04169575A JPH04169575A JP29300790A JP29300790A JPH04169575A JP H04169575 A JPH04169575 A JP H04169575A JP 29300790 A JP29300790 A JP 29300790A JP 29300790 A JP29300790 A JP 29300790A JP H04169575 A JPH04169575 A JP H04169575A
- Authority
- JP
- Japan
- Prior art keywords
- perhydrotriazine
- dithione
- compound
- formula
- imino
- 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.)
- Granted
Links
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- -1 isothiocyanic acid ester Chemical class 0.000 claims abstract description 6
- 239000002798 polar solvent Substances 0.000 claims abstract description 6
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 5
- 125000003118 aryl group Chemical group 0.000 claims abstract description 5
- 239000000126 substance Substances 0.000 claims 1
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 abstract description 24
- 150000001875 compounds Chemical class 0.000 abstract description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 10
- 239000002904 solvent Substances 0.000 abstract description 3
- 239000003054 catalyst Substances 0.000 abstract description 2
- 239000011541 reaction mixture Substances 0.000 abstract description 2
- 239000011347 resin Substances 0.000 abstract description 2
- 229920005989 resin Polymers 0.000 abstract description 2
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 abstract 2
- 239000003607 modifier Substances 0.000 abstract 1
- 238000000746 purification Methods 0.000 abstract 1
- 238000005292 vacuum distillation Methods 0.000 abstract 1
- LGDSHSYDSCRFAB-UHFFFAOYSA-N Methyl isothiocyanate Chemical compound CN=C=S LGDSHSYDSCRFAB-UHFFFAOYSA-N 0.000 description 22
- 238000006243 chemical reaction Methods 0.000 description 12
- 239000004809 Teflon Substances 0.000 description 6
- 229920006362 Teflon® Polymers 0.000 description 6
- DCAYPVUWAIABOU-UHFFFAOYSA-N hexadecane Chemical compound CCCCCCCCCCCCCCCC DCAYPVUWAIABOU-UHFFFAOYSA-N 0.000 description 6
- 239000013638 trimer Substances 0.000 description 6
- QKFJKGMPGYROCL-UHFFFAOYSA-N phenyl isothiocyanate Chemical compound S=C=NC1=CC=CC=C1 QKFJKGMPGYROCL-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 239000002808 molecular sieve Substances 0.000 description 3
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 3
- 230000003595 spectral effect Effects 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 229940117953 phenylisothiocyanate Drugs 0.000 description 2
- 230000001766 physiological effect Effects 0.000 description 2
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 2
- AHDSRXYHVZECER-UHFFFAOYSA-N 2,4,6-tris[(dimethylamino)methyl]phenol Chemical compound CN(C)CC1=CC(CN(C)C)=C(O)C(CN(C)C)=C1 AHDSRXYHVZECER-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 150000007973 cyanuric acids Chemical class 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 125000001841 imino group Chemical group [H]N=* 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 239000012970 tertiary amine catalyst Substances 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
Abstract
Description
【発明の詳細な説明】
［産業上の利用分野］
本発明は、６−イミツー１，３．５−）−り置換−１，
３，５−パーヒドロトリアジン−２，４−ジチオン誘導
体の製造方法に関するもので、より詳細にはこれらの化
合物を、イソチオシアン酸エステルを塩基の存在下、極
性溶媒中で高圧をかけて反応させることにより簡単かつ
収率よく構造する方法に関するものである。Detailed Description of the Invention [Industrial Field of Application] The present invention provides 6-imitsu-1,3.5-)-substituted-1,
It relates to a method for producing 3,5-perhydrotriazine-2,4-dithione derivatives, and more specifically, it involves reacting these compounds with isothiocyanate esters in the presence of a base in a polar solvent under high pressure. The present invention relates to a method for constructing a structure more simply and with high yield.
類似の構造を持つ１，３．５−パーヒドロトリアジン−
２，４，６−トリオン誘導体及びトリチオン誘導体が種
々の生理活性を示すことが知られており、本化合物は活
性なイミノ基を更に含んでいるため高い生理活性を示す
ことが期待される６また本化合物は加水分解により容易
に１．３．５−パーヒドロトリアジン−２，４−ジチオ
ン−６−オン誘導体に変換できるが、この化合物はイソ
シアヌル酸誘導体と類似の化合物であることから樹脂の
改質剤としての用途も期待できる。1,3,5-perhydrotriazine- with a similar structure
It is known that 2,4,6-trione derivatives and trithione derivatives exhibit various physiological activities, and this compound is expected to exhibit high physiological activity because it further contains an active imino group. This compound can be easily converted into a 1.3.5-perhydrotriazine-2,4-dithion-6-one derivative by hydrolysis, but since this compound is similar to isocyanuric acid derivatives, it can be used to modify resins. It is also expected to be used as a quality agent.
［従来技術］
このように６−イミノ−１，３，５−トリ置換−１，３
，５−パーヒドロトリアジン−２，４−ジチオン誘導体
は有用な化合物であり、チオ尿素からの合成法（Ｂｕｌ
ｌ 、 Ｃｈｅｍ 、Ｓｏ’ｃ 、 Ｊｐｎ 、 、
５９ 、３６９３（１９８６））などが知られているが
、ブチルリチウムを使うなど実際的ではなかった。[Prior art] In this way, 6-imino-1,3,5-tri-substituted-1,3
,5-perhydrotriazine-2,4-dithione derivatives are useful compounds and have been developed using a synthetic method from thiourea (Bul
l, Chem, So'c, Jpn, ,
59, 3693 (1986)), but it was not practical to use butyllithium.
［発明が解決しようとする問題点コ
従って、本発明の目的は６−イミツー１，３゜５−トリ
置換−１，３，５−パーヒドロトリアジン−２，４−ジ
チオン誘導体の効率的な製造方法を開発することである
。[Problems to be Solved by the Invention] Therefore, the purpose of the present invention is to efficiently produce 6-imi2-1,3゜5-trisubstituted-1,3,5-perhydrotriazine-2,4-dithione derivatives. The goal is to develop methods.
［問題点を解決するための手段］
本発明者らは、高圧条件下、極性溶媒中でイソチオシア
ン酸エステルを塩基と微量の水分の存在・ 下に反応さ
せることにより６−イミツー１，３゜５−トリ置換−１
，３，５−パーヒドロトリアジン−２，４−ジチオンの
誘導体を高収率で製造で；漬ることを見いだし、本発明
を完成するに至った。[Means for Solving the Problems] The present inventors prepared 6-imitsu 1,3゜5 by reacting an isothiocyanate ester with a base in a polar solvent under high pressure conditions in the presence of a trace amount of water. -Tri substitution-1
, 3,5-perhydrotriazine-2,4-dithione derivatives can be produced in high yields, leading to the completion of the present invention.
すなわち本発明は、−数式（Ｉ）ＲＮＣ５（式中、Ｒは
アルキル基又はアリール基を示す。）で表わされるイソ
チオシアン酸エステルを塩基の存在下、極性溶媒中で高
圧をかけて反応することを特徴とする一般式（ＩＩ）
！
（式中、Ｒはアルキル基又はアリール基を示す。）で表
わされる６−イミノ−１，３，５−トリ置換−１，３，
５−パーヒドロトリアジン−２，４−ジチオン誘導体の
製造方法を提供するものである。That is, the present invention involves reacting an isothiocyanate ester represented by the formula (I) RNC5 (wherein R represents an alkyl group or an aryl group) in a polar solvent under high pressure in the presence of a base. Featured general formula (II)! (In the formula, R represents an alkyl group or an aryl group.) 6-imino-1,3,5-trisubstituted-1,3,
A method for producing a 5-perhydrotriazine-2,4-dithione derivative is provided.
次に本発明における目的化合物（ｎ）の生成経路を塩基
としてトリエチルアミンを用いたインチオシアン酸メチ
ルの反応を例にとれば、式（ＩＩＩ）本発明の反応は、
通常ＤＭＦなどの極性溶媒中、第三級アミン触媒の存在
下、微量の水分を添加して（市販溶媒中に含まれる量で
可）高圧条件下で行われる。例えば、トリエチルアミン
、Ｎ−メチルモルホリン、ピリジン等が触媒として用い
られた。圧力は高圧はど好ましいが、一般には１０００
〜１２０００ｋｇ／ａｄ（７）範Ｈ’ｔ’選択すｔＬル
。Next, if we take as an example the reaction of methyl inthiocyanate using triethylamine as a base, the reaction of formula (III) of the present invention is as follows:
It is usually carried out in a polar solvent such as DMF in the presence of a tertiary amine catalyst under high pressure conditions with the addition of a trace amount of water (an amount contained in a commercially available solvent is acceptable). For example, triethylamine, N-methylmorpholine, pyridine, etc. were used as catalysts. High pressure is preferable, but generally 1000
~12000kg/ad (7) Range H't' Select tL.
反応温度は特に制約されないが、副反応の進行を抑制す
る意味では、室温〜１００℃の温度の採用が好ましい０
反応時間は圧力、温度等に左右されるが、通常１〜５０
時間で十分である。The reaction temperature is not particularly limited, but in order to suppress the progress of side reactions, it is preferable to use a temperature between room temperature and 100°C.
The reaction time depends on pressure, temperature, etc., but is usually 1 to 50 minutes.
Time is enough.
反応混合物から溶媒を留去した後、減圧蒸留とカラムク
ロマトグラフィーにより本発明の目的化合物が純度よく
得られる。かくして得られた目的葎金物は、ＩＲ，ＮＭ
Ｒ，ＭＳを分析することによりその構造を確認できる。After distilling off the solvent from the reaction mixture, the target compound of the present invention can be obtained with high purity by distillation under reduced pressure and column chromatography. The objective hardware thus obtained is IR, NM.
The structure can be confirmed by analyzing R, MS.
［発明の効果コ
本発明方法によれば、６−イミノ−１，３，５−トリ置
換−１，３，５−パーヒドロトリアジン−２，４−ジチ
オン誘導体を高収率かつ効率的に製造することができる
。[Effects of the Invention] According to the method of the present invention, 6-imino-1,3,5-trisubstituted-1,3,5-perhydrotriazine-2,4-dithione derivatives can be produced efficiently in high yield. can do.
［実施例］ 以下、実施例に基づき、本発明を更に詳細に説明する。[Example] Hereinafter, the present invention will be explained in more detail based on Examples.
実施例１
テフロンチューブにイソチオシアン酸メチル０゜３７ｇ
、トリエチルアミン０．０５ｇ及び市販の特級ＤＭＦ３
ｍｌを封入し、８０００ｋｇ／ａｄに加圧して、４０℃
で２０時間反応した。常圧に戻し、減圧蒸留後、シリカ
ゲルを用いたカラムクロマトグラフィー（ベンゼン：酢
エチ ９：１）により６−メチルイミノ−１，３，５−
トリメチル−１゜３．５−パーヒドロトリアジン−２，
４−ジチオンを単離し、収率７４％を得た。Example 1 0°37g of methyl isothiocyanate in a Teflon tube
, triethylamine 0.05g and commercially available special grade DMF3
ml, pressurized to 8000 kg/ad, and heated at 40°C.
The reaction was carried out for 20 hours. After returning to normal pressure and distilling under reduced pressure, 6-methylimino-1,3,5-
Trimethyl-1゜3.5-perhydrotriazine-2,
4-dithione was isolated with a yield of 74%.
この化合物のスペクトルデータは文献の報告（Ｂｕｌｌ
、Ｃｈｅｍ、Ｓｏｃ、Ｊｐｎ、 、５９，３６９３（１
９８６）） と一致した。Spectral data for this compound are reported in the literature (Bull
, Chem, Soc, Jpn, , 59,3693 (1
986)).
ＩＲ：１６７９ｃｍ−１ ＮＭＲ： ３．９３ （ｓ、３Ｈ，ＣＨ，）。IR: 1679cm-1 NMR: 3.93 (s, 3H, CH,).
３、６２ （ｓ 、６Ｈ９２ＣＨ３） 。3, 62 (s, 6H92CH3).
３．２７ （ｓ、３Ｈ２ＣＨ３）
ＭＳ ：２１６
また、同様の反応を封管中で行なうと目的物はまったく
得られなかった。3.27 (s, 3H2CH3) MS: 216 Furthermore, when the same reaction was carried out in a sealed tube, the target product was not obtained at all.
実施例２
実施例１と同様にテフロンチューブにイソチオシアン酸
メチル０．３７ｇ、トリエチルアミン０゜０５ｇ、モリ
キュラーシーブにより乾燥したＤＭＦ３ｍｌ及び純水５
μｌを封入し、８０００ｋｇ／ｄに加圧して、４０”Ｃ
で２０時間反応した。ヘキサデカン０．１ｇを内部標準
として加えたＧＬＣ分析では、６−メチルイミノ−１，
３，５−トリメチル−１，３，５−パーヒドロトリアジ
ン−２゜４−ジチオン５３％とイソチオシアン酸メチル
の三量体７％が得られた。Example 2 In the same manner as in Example 1, 0.37 g of methyl isothiocyanate, 0.05 g of triethylamine, 3 ml of DMF dried with a molecular sieve, and 5 ml of pure water were placed in a Teflon tube.
μl was sealed, pressurized to 8000 kg/d, and 40”C
The reaction was carried out for 20 hours. In GLC analysis using 0.1 g of hexadecane as an internal standard, 6-methylimino-1,
53% of 3,5-trimethyl-1,3,5-perhydrotriazine-2°4-dithione and 7% of a trimer of methyl isothiocyanate were obtained.
この反応を純水を加えずに行なうと６−メチルイミノ−
１，３，５−）−ツメチル−１，３，５−パーヒドロト
リアジン−２，４−ジチオン４％とイソチオシアン酸メ
チルの三量体２８％が得られ、微量の水分の効果が認め
られた。If this reaction is carried out without adding pure water, 6-methylimino-
4% of 1,3,5-)-tumethyl-1,3,5-perhydrotriazine-2,4-dithione and 28% of a trimer of methyl isothiocyanate were obtained, and the effect of a small amount of water was observed. .
実施例３
実施例１と同様にテフロンチューブにイソチオシアン酸
メチル０．３７ｇ、トリエチルアミン０゜０５ｇ、モリ
キュラーシーブにより乾燥したＤＭＦ ３ ｍ ｌ及び
純水１０μｌを封入し、８０００ｋｇ／ｄに加圧して、
４０℃で２０時間反応した。ヘキサデカン０６１ｇを内
部標準として加えたＧＬＣ分析では、６−メチルイミノ
−１，３，５−トリメチル−１，３，５−パーヒドロト
リアジン−２，４−ジチオン３１％とイソチオシアン酸
メチルの三量体１５％が得られた。Example 3 In the same manner as in Example 1, 0.37 g of methyl isothiocyanate, 0.05 g of triethylamine, 3 ml of DMF dried with a molecular sieve, and 10 μl of pure water were sealed in a Teflon tube, and the tube was pressurized to 8000 kg/d.
The reaction was carried out at 40°C for 20 hours. GLC analysis using 061 g of hexadecane as an internal standard revealed that 31% of 6-methylimino-1,3,5-trimethyl-1,3,5-perhydrotriazine-2,4-dithione and 15% of the trimer of methyl isothiocyanate %was gotten.
この反応を純水を加えずに行なうと６−メチルイミノ−
１，３，５−トリメチル−１，３，５−パーヒドロトリ
アジン−２，４−ジチオンはほとんど得られず、イソチ
オシアン酸メチルの三量体８７％が得られ、微量の水分
の効果が認められた。If this reaction is carried out without adding pure water, 6-methylimino-
Almost no 1,3,5-trimethyl-1,3,5-perhydrotriazine-2,4-dithione was obtained, and 87% of the trimer of methyl isothiocyanate was obtained, and the effect of a small amount of water was observed. Ta.
実施例４
実施例１と同様にテフロンチューブにイソチオシアン酸
メチル０．３７ｇ、トリブチルアミン０゜０９ｇ、モリ
キュラーシーブにより乾燥したＤＭＦ３ｍｌ及び純水１
ｏμｌを封入し、８０００ｋｇ／ｄに加圧して、４０℃
で２０時間反応した。ヘキサデカン０．１ｇを内部標準
として加えたＧＬＣ分析では、６−メチルイミノ−１，
３，５−トリメチル−１，３，５−パーヒドロトリアジ
ン−２，４−ジチオン５９％とイソチオシアン酸メチル
の三量体１８％が得られた。Example 4 In the same manner as in Example 1, 0.37 g of methyl isothiocyanate, 0.09 g of tributylamine, 3 ml of DMF dried with a molecular sieve, and 1 ml of pure water were placed in a Teflon tube.
oμl was sealed, pressurized to 8000 kg/d, and heated at 40°C.
The reaction was carried out for 20 hours. In GLC analysis using 0.1 g of hexadecane as an internal standard, 6-methylimino-1,
59% of 3,5-trimethyl-1,3,5-perhydrotriazine-2,4-dithione and 18% of a trimer of methyl isothiocyanate were obtained.
実施例５
テフロンチューブにイソチオシアン酸メチル０゜４４ｇ
、トリエチルアミン０．０５ｇ及び市販の特級ＤＭＦ３
ｍｌを封入し、１２０００ｋｇ／ａ＃に加圧して、４０
℃で２０時間反応した。常圧に戻し、減圧蒸留後、シリ
カゲルを用いたカラムクロマトグラフィー（ベンゼン：
酢エチ ９：１）に９１す６−エチルイミノ−１，３，
５−トリエチル−１，３，５−パーヒドロトリアジン−
２，４−ジチオン３７％とイソチオシアン酸メチルの三
量体１１％を単離した。Example 5 0°44g of methyl isothiocyanate in a Teflon tube
, triethylamine 0.05g and commercially available special grade DMF3
ml, pressurized to 12000 kg/a#, 40
The reaction was carried out at ℃ for 20 hours. After returning to normal pressure and distilling under reduced pressure, column chromatography using silica gel (benzene:
ethyl acetate 9:1) to 91su6-ethylimino-1,3,
5-Triethyl-1,3,5-perhydrotriazine-
37% of 2,4-dithione and 11% of methyl isothiocyanate trimer were isolated.
この化合物のスペクトルデータを下記に示す。The spectral data of this compound is shown below.
ＩＲ：１６６８ｃｍ−１
ＮＭＲ： ４．８３ （ｑｕａｌ、 ２Ｈ，ＣＨ２）
。IR: 1668 cm-1 NMR: 4.83 (qual, 2H, CH2)
.
４．３７ （ｑｕａｌ、４Ｈ，２ＣＨ２）。4.37 (qual, 4H, 2CH2).
３、４３ （ｑｕａｌ、 ２Ｈ，ＣＨ２）１、 １−１
． ７５
（ｍ、１２Ｈｔ ４ＣＨ３）＋
実施例６
テフロンチューブにイソチオシアン酸フェニル０．６８
ｇ、トリエチルアミン０．０５ｇ及び市販の特級ＤＭＦ
３ｍｌを封入し、１２０００ｋｇ／ｄに加圧して、４０
℃で２０時間反応した。常圧に戻した後、ＤＭＦ及び未
反応のイソチオシアン酸フェニルを減圧蒸留後、２０ｍ
１のエタノールを加え加熱還流した。冷却後、沈澱物を
ろ過乾燥することにより６−フエニルイミツー１．３．
５−トリフェニル−１，３，５−パーヒドロトリアジン
−２，４−ジチオン４１％を単離した。3, 43 (qual, 2H, CH2) 1, 1-1
．． 75 (m, 12Ht 4CH3)+ Example 6 Phenyl isothiocyanate 0.68 in Teflon tube
g, triethylamine 0.05 g and commercially available special grade DMF
3 ml was sealed, pressurized to 12,000 kg/d, and
The reaction was carried out at ℃ for 20 hours. After returning to normal pressure, DMF and unreacted phenyl isothiocyanate were distilled under reduced pressure.
1 of ethanol was added and heated to reflux. After cooling, the precipitate was filtered and dried to obtain 6-phenyl imizate 1.3.
41% of 5-triphenyl-1,3,5-perhydrotriazine-2,4-dithione was isolated.
この化合物のスペクトルデータを下記に示す。The spectral data of this compound is shown below.
ＩＲ：１６８２ｃａ＋−１ ＮＭＲニア、３３−７．５３ （ｍ、５Ｈ，ＣＧＨ５）。IR: 1682ca+-1 NMR near, 33-7.53 (m, 5H, CGH5).
７．２２ （ｓ、１０Ｈ，２Ｃ−Ｈｓ） 。7.22 (s, 10H, 2C-Hs).
６．５８−６．８５ （ｍ ｙ ５ Ｈｙ Ｃｓ Ｈｓ ） ＭＳ ：４６４6.58-6.85 (m y 5 Hy Cs Hs) MS: 464
Claims (1)
わされるイソチオシアン酸エステルを塩基の存在下、 極性溶媒中で高圧をかけて反応することを特徴とする一
般式（II） ▲数式、化学式、表等があります▼ （式中、Ｒはアルキル基又はアリール基を示す。）で表
わされる６−イミノ−１，３，５−トリ置換−１，３，
５−パ−ヒドロトリアジン−２，４−ジチオン誘導体の
製造方法。(1) It is characterized by reacting an isothiocyanate ester represented by the general formula (I) RNCS (in the formula, R represents an alkyl group or an aryl group) in a polar solvent under high pressure in the presence of a base. General formula (II) ▲ Numerical formulas, chemical formulas, tables, etc. are available ▼ (In the formula, R represents an alkyl group or an aryl group.) 6-imino-1,3,5-trisubstituted-1,3 ，
A method for producing a 5-perhydrotriazine-2,4-dithione derivative.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP29300790A JPH04169575A (en) | 1990-10-30 | 1990-10-30 | Production of 6-imino-1,3,5-trisubstituted-1,3,5-perhydrotriazine-2,4-dithione derivative |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP29300790A JPH04169575A (en) | 1990-10-30 | 1990-10-30 | Production of 6-imino-1,3,5-trisubstituted-1,3,5-perhydrotriazine-2,4-dithione derivative |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH04169575A true JPH04169575A (en) | 1992-06-17 |
| JPH0579670B2 JPH0579670B2 (en) | 1993-11-04 |
Family
ID=17789272
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP29300790A Granted JPH04169575A (en) | 1990-10-30 | 1990-10-30 | Production of 6-imino-1,3,5-trisubstituted-1,3,5-perhydrotriazine-2,4-dithione derivative |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH04169575A (en) |
-
1990
- 1990-10-30 JP JP29300790A patent/JPH04169575A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0579670B2 (en) | 1993-11-04 |
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