JPH058703B2 - - Google Patents
Info
- Publication number
- JPH058703B2 JPH058703B2 JP60052543A JP5254385A JPH058703B2 JP H058703 B2 JPH058703 B2 JP H058703B2 JP 60052543 A JP60052543 A JP 60052543A JP 5254385 A JP5254385 A JP 5254385A JP H058703 B2 JPH058703 B2 JP H058703B2
- Authority
- JP
- Japan
- Prior art keywords
- phthalimide
- cyclohexylthio
- organic solvent
- layer
- solution
- 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 - Fee Related
Links
- UEZWYKZHXASYJN-UHFFFAOYSA-N cyclohexylthiophthalimide Chemical compound O=C1C2=CC=CC=C2C(=O)N1SC1CCCCC1 UEZWYKZHXASYJN-UHFFFAOYSA-N 0.000 claims description 17
- 239000003960 organic solvent Substances 0.000 claims description 17
- 150000001412 amines Chemical class 0.000 claims description 10
- XRFDWTWFFLOKAV-UHFFFAOYSA-N cyclohexyl thiohypochlorite Chemical compound ClSC1CCCCC1 XRFDWTWFFLOKAV-UHFFFAOYSA-N 0.000 claims description 9
- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 claims description 8
- 239000003513 alkali Substances 0.000 claims description 7
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 5
- 239000011707 mineral Substances 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- ZZKZVYKAXYQGTK-UHFFFAOYSA-N 4-cyclohexylsulfanylisoindole-1,3-dione Chemical compound O=C1NC(=O)C2=C1C=CC=C2SC1CCCCC1 ZZKZVYKAXYQGTK-UHFFFAOYSA-N 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- 239000000243 solution Substances 0.000 description 13
- 239000013078 crystal Substances 0.000 description 11
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 239000007864 aqueous solution Substances 0.000 description 9
- 239000007787 solid Substances 0.000 description 8
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 8
- 238000000034 method Methods 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- 229910052801 chlorine Inorganic materials 0.000 description 4
- 238000004811 liquid chromatography Methods 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- ODHAQPXNQDBHSH-UHFFFAOYSA-N Dicyclohexyl disulfide Chemical compound C1CCCCC1SSC1CCCCC1 ODHAQPXNQDBHSH-UHFFFAOYSA-N 0.000 description 3
- 235000010755 mineral Nutrition 0.000 description 3
- 235000011121 sodium hydroxide Nutrition 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000007810 chemical reaction solvent Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- CMKBCTPCXZNQKX-UHFFFAOYSA-N cyclohexanethiol Chemical compound SC1CCCCC1 CMKBCTPCXZNQKX-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 239000003518 caustics Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 150000003949 imides Chemical class 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 229920003052 natural elastomer Polymers 0.000 description 1
- 229920001194 natural rubber Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 229920003051 synthetic elastomer Polymers 0.000 description 1
- 239000005061 synthetic rubber Substances 0.000 description 1
- 150000003512 tertiary amines Chemical group 0.000 description 1
- 238000004073 vulcanization Methods 0.000 description 1
Landscapes
- Indole Compounds (AREA)
Description
【発明の詳細な説明】
＜産業上の利用分野＞
本発明は高純度Ｎ−（シクロヘキシルチオ）−フ
タルイミドの製法に関する。Ｎ−（シクロヘキシ
ルチオ）−フタルイミドは天然ゴムまたは合成ゴ
ムの早期加硫抑制剤として極めて有用な化合物で
ある。DETAILED DESCRIPTION OF THE INVENTION <Industrial Application Field> The present invention relates to a method for producing highly pure N-(cyclohexylthio)-phthalimide. N-(cyclohexylthio)-phthalimide is a very useful compound as an early vulcanization inhibitor for natural or synthetic rubber.
＜従来の技術＞
Ｎ−（シクロヘキシルチオ）−フタルイミドはフ
タルイミドとシクロヘキシルスルフエニルクロラ
イドとを有機溶媒中で反応（イミド反応）させて
製造するのが一般的であり、この時生成する塩化
水素をトラツプするために有機アミンを反応系中
に共存させる方法（特公昭47−6499号公報、およ
び特公昭49−22940号公報）がしられている。<Prior art> N-(cyclohexylthio)-phthalimide is generally produced by reacting phthalimide and cyclohexylsulfenyl chloride in an organic solvent (imide reaction), and the hydrogen chloride produced at this time is A method of coexisting an organic amine in the reaction system for trapping is known (Japanese Patent Publication No. 47-6499 and Japanese Patent Publication No. 49-22940).
一方、この反応の原料であるシクロヘキシルス
ルフエニルクロライドの製法としてはいくつかの
方法が報告されているが、シクロヘキシルチオー
ルまたはジシクロヘキシルジスルフイドを有機溶
媒中で塩素と反応させる方法が一般的である。 On the other hand, several methods have been reported for producing cyclohexylsulfenyl chloride, which is the raw material for this reaction, but the most common method is to react cyclohexylthiol or dicyclohexyl disulfide with chlorine in an organic solvent. .
またシクロヘキシルスルフエニルクロライドは
非常に不安定であり、有機溶媒中で速やかに分解
する。（J.Org.Chem.34.51〜55（1969）に記載のJ.
E.Kerwoodらの研究）。 Furthermore, cyclohexylsulfenyl chloride is very unstable and rapidly decomposes in organic solvents. (J.Org.Chem.34.51-55 (1969))
E. Kerwood et al.).
従つて、上記公知例に従つてシクロヘキシルス
ルフエニルクロライドとフタルイミドからＮ−
（シクロヘキシルチオ）−フタルイミドを製造する
場合、有機溶媒中でシクロヘキシルチオールまた
はジシクロヘキシルジスルフイドと塩素を反応さ
せて得た反応液を精製することなくそのままフタ
ルイミドと混合するのが工業的に有利な方法であ
る。 Therefore, according to the above-mentioned known example, N-
When producing (cyclohexylthio)-phthalimide, an industrially advantageous method is to react the reaction solution obtained by reacting cyclohexylthiol or dicyclohexyl disulfide with chlorine in an organic solvent and mix it with phthalimide as it is without purifying it. It is.
＜発明が解決しようとする問題点＞
本発明者らは有機溶媒中でジシクロヘキシルジ
スルフイドと塩素とを反応させて得た反応液とフ
タルイミドとを有機アミンの共存下で反応させＮ
−（シクロヘキシルチオ）−フタルイミドの合成を
試みたが、Ｎ−（シクロヘキシルチオ）−フタルイ
ミドの品質が悪く製品規格にほど遠い製品しか得
られなかつた。<Problems to be Solved by the Invention> The present inventors reacted a reaction solution obtained by reacting dicyclohexyl disulfide with chlorine in an organic solvent with phthalimide in the coexistence of an organic amine.
An attempt was made to synthesize -(cyclohexylthio)-phthalimide, but the quality of N-(cyclohexylthio)-phthalimide was poor and the product could only be obtained which did not meet the product specifications.
従つて本発明の課題は、高純度のＮ−（シクロ
ヘキシルチオ）−フタルイミドを工業的に有利に
製造する方法を提供することにある。 Therefore, an object of the present invention is to provide an industrially advantageous method for producing highly pure N-(cyclohexylthio)-phthalimide.
＜問題点を解決するための手段および作用＞
本発明の上記課題は有機アミンと有機溶媒の存
在下にフタルイミドとシクロヘキシルスルフエニ
ルクロライドとを反応させ、次いで生成反応液中
の有機アミンを鉱酸で中和させて鉱酸塩として水
層に移行せしめ、残る有機溶媒層にアルカリ水溶
液を混合させた後有機溶媒層と水層に分液し、次
いで該有機溶媒層からＮ−（シクロヘキシルチオ）
−フタルイミドを晶析させることを特徴とする高
純度Ｎ−（シクロヘキシルチオ）−フタルイミドの
製法により達成された。<Means and effects for solving the problems> The above-mentioned problem of the present invention is to react phthalimide and cyclohexylsulfenyl chloride in the presence of an organic amine and an organic solvent, and then to remove the organic amine in the reaction solution with a mineral acid. The remaining organic solvent layer is mixed with an alkaline aqueous solution, separated into an organic solvent layer and an aqueous layer, and then N-(cyclohexylthio) is neutralized from the organic solvent layer.
This was achieved by a method for producing highly pure N-(cyclohexylthio)-phthalimide, which is characterized by crystallizing -phthalimide.
本発明に従えば、有機アミンの存在下有機溶媒
中でフタルイミドとシクロヘキシルスルフエニル
クロライドから得られるＮ−（シクロヘキシルチ
オ）−フタルイミドの反応液中の有機アミンを鉱
酸で中和し、鉱酸塩として水層へ回収し、一方有
機溶媒層にアルカリ水溶液を加えて混合し、未反
応のフタルイミドや不純物をアルカリ水溶液中に
移行せしめ、有機溶媒層から目的物Ｎ−（シクロ
ヘキシルチオ）−フタルイミドを晶析することに
より、高純度のＮ−（シクロヘキシルチオ）−フタ
ルイミドが取得されるのである。 According to the present invention, the organic amine in the reaction solution of N-(cyclohexylthio)-phthalimide obtained from phthalimide and cyclohexylsulfenyl chloride in an organic solvent in the presence of an organic amine is neutralized with a mineral acid. It is recovered as a salt into the aqueous layer, and on the other hand, an aqueous alkali solution is added to the organic solvent layer and mixed to transfer unreacted phthalimide and impurities into the aqueous alkali solution, and the target product N-(cyclohexylthio)-phthalimide is removed from the organic solvent layer. By crystallizing, highly pure N-(cyclohexylthio)-phthalimide is obtained.
本発明においてアルカリ水溶液としてはアルカ
リ金属水酸化物の水溶液が好ましく用いられ、そ
の濃度は通常0.1重量％〜40重量％で好ましくは
１重量％〜５重量％である。 In the present invention, an aqueous solution of an alkali metal hydroxide is preferably used as the aqueous alkali solution, and its concentration is usually 0.1% to 40% by weight, preferably 1% to 5% by weight.
アルカリ水溶液の混合量は、アルカリ化合物の
量として、イミド化反応に使用したシクロヘキシ
ルスルフエニルクロライド１モルに対して通常
0.01モルから0.20で好ましくは0.05モルから0.15
モルである。 The amount of alkali aqueous solution mixed is usually the amount of alkali compound per mole of cyclohexylsulfenyl chloride used in the imidization reaction.
0.01 mol to 0.20, preferably 0.05 mol to 0.15
It is a mole.
本発明においてアルカリ水溶液の混合時の温度
は高温すぎるとアルカリ水溶液により目的物であ
るＮ−（シクロヘキシルチオ）−フタルイミドが分
解してしまう恐れがあるので室温付近が好まし
い。 In the present invention, the temperature at which the alkaline aqueous solution is mixed is preferably around room temperature because if the alkali aqueous solution is too high, the target product, N-(cyclohexylthio)-phthalimide, may be decomposed by the alkaline aqueous solution.
本発明で使用する有機アミンは特に限定するも
のではないが、反応溶媒に溶ける３級アミンで好
ましくはトリエチルアミンである。有機アミンを
除去するために使用する鉱酸は反応溶媒と反応し
ないものであれば特に限定するものではないが好
ましくは塩酸および硫酸である。 The organic amine used in the present invention is not particularly limited, but is a tertiary amine that is soluble in the reaction solvent, and is preferably triethylamine. The mineral acid used to remove the organic amine is not particularly limited as long as it does not react with the reaction solvent, but hydrochloric acid and sulfuric acid are preferred.
本発明において使用される有機溶媒はＮ−（シ
クロヘキシルチオ）−フタルイミドをよく溶かし
塩素に対して安定なもので例えば四塩化炭素が好
ましく使用される。 The organic solvent used in the present invention is one that dissolves N-(cyclohexylthio)-phthalimide well and is stable against chlorine, such as carbon tetrachloride.
以下、実施例によつて本発明をさらに具体的に
説明する。 Hereinafter, the present invention will be explained in more detail with reference to Examples.
＜実施例＞
実施例 １
かきまぜ機、温度計、滴下ロートを備えたガラ
ス製四つ口フラスコの中に純度98％のフタルイミ
ド30.0g（0.2モル）と純度99％以上の四塩化炭素
200gとそして純度99％以上のトリエチルアミン
26.3gを入れ室温下でかきまぜた。<Example> Example 1 30.0 g (0.2 mol) of phthalimide with a purity of 98% and carbon tetrachloride with a purity of 99% or more in a four-necked glass flask equipped with a stirrer, a thermometer, and a dropping funnel.
200g and more than 99% purity triethylamine
Add 26.3g and stir at room temperature.
この中へ四塩化炭素を溶媒としたシクロヘキシ
ルスルフエニルクロライドの溶液200g（0.2モルの
シクロヘキシルスルフエニルクロライドが溶解し
ている）を定量ポンプにより１時間で供給した。 200 g of a solution of cyclohexylsulfenyl chloride (0.2 mol of cyclohexylsulfenyl chloride dissolved therein) using carbon tetrachloride as a solvent was fed into the solution over 1 hour using a metering pump.
供給終了後も30分間、室温下でかきまぜを継続
した。３％の塩酸水溶液72.9gを滴下ロートより
徐々に添加し過剰分のトリエチルアミンを中和し
た。 Stirring was continued at room temperature for 30 minutes after the end of the supply. 72.9 g of a 3% aqueous hydrochloric acid solution was gradually added from the dropping funnel to neutralize the excess triethylamine.
内液を分液ロートに移液した上層と下層を分離
した。下層を四つ口フラスコに移液し、その中へ
２％苛性ソーダ水溶液50gを入れ室温下で１時間
かきまぜた。内液を分液ロートに移液し上層と下
層を分離した。下層を２等分し一方の液からロー
タリーエバポレータで四塩化炭素を留去させたあ
と室温5Torr.以下の真空乾燥器で一夜乾燥し固
形物25.0gを得た。固形物の融点は89〜90℃でＮ
−（シクロヘキシルチオ）−フタルイミドの純度は
液体クロマトグラフイで分析した結果95.8％であ
つた。 The internal solution was transferred to a separating funnel and separated into an upper layer and a lower layer. The lower layer was transferred to a four-necked flask, and 50 g of a 2% aqueous sodium hydroxide solution was added thereto, followed by stirring at room temperature for 1 hour. The internal solution was transferred to a separating funnel to separate the upper and lower layers. The lower layer was divided into two equal parts, carbon tetrachloride was distilled off from one liquid using a rotary evaporator, and the mixture was dried overnight in a vacuum dryer at room temperature of 5 Torr or less to obtain 25.0 g of a solid. The melting point of solids is N at 89-90℃
The purity of -(cyclohexylthio)-phthalimide was 95.8% as analyzed by liquid chromatography.
もう一方の液をロータリエバポレータで濃縮し
Ｎ−（シクロヘキシルチオ）−フタルイミドの結晶
を析出させた。 The other liquid was concentrated using a rotary evaporator to precipitate crystals of N-(cyclohexylthio)-phthalimide.
この結晶を過鐘で分離したあと、室温、
5Torr.以下の真空乾燥器で一夜乾燥し結晶14.6g
を得た。結晶の融点は93〜94℃でＮ−（シクロヘ
キシルチオ）−フタルイミドの液体クロマトグラ
フイによる純度は99.7％であつた。 After separating these crystals using a filter, the crystals were separated at room temperature.
Dry overnight in a vacuum dryer at 5 Torr or less to obtain 14.6 g of crystals.
I got it. The melting point of the crystals was 93-94°C, and the purity of N-(cyclohexylthio)-phthalimide by liquid chromatography was 99.7%.
実施例 ２
実施例１の苛性ソーダ水溶液を苛性カリ水溶液
に代えた以外は実施例１と同じ方法で行なつた。Example 2 The same method as in Example 1 was carried out except that the caustic soda aqueous solution in Example 1 was replaced with a caustic potassium aqueous solution.
その結果、濃縮固形物24.9g、晶析結晶14.6gを
得た。融点は濃縮固形物で89〜90℃、晶析結晶で
93〜94℃であつた。 As a result, 24.9 g of concentrated solid matter and 14.6 g of crystallized crystals were obtained. The melting point is 89-90℃ for concentrated solids, and for crystallized crystals.
The temperature was 93-94℃.
Ｎ−（シクロヘキシルチオ）−フタルイミドの液
体クロマトグラフイによる純度は濃縮固形物で
95.6％、晶析結晶で99.6％であつた。 The purity of N-(cyclohexylthio)-phthalimide by liquid chromatography is determined by the concentration of solid matter.
It was 95.6%, and 99.6% in crystallized crystals.
比較例
実施例１の苛性ソーダ水溶液処理を行なわなか
つた以外は実施例１と同じ方法で行なつた。Comparative Example The same method as in Example 1 was carried out except that the caustic soda aqueous solution treatment in Example 1 was not performed.
その結果、濃縮固形物26.0g、晶析結晶14.7gを
得た。融点は濃縮固形物で88〜89℃、晶析結晶で
91〜92℃であつた。 As a result, 26.0 g of concentrated solid matter and 14.7 g of crystallized crystals were obtained. The melting point is 88-89℃ for concentrated solids, and for crystallized crystals.
The temperature was 91-92℃.
Ｎ−（シクロヘキシルチオ）−フタルイミドの液
体クロマトグラフイによる純度は濃縮固形物で
92.3％、晶析結晶で97.2％であつた。 The purity of N-(cyclohexylthio)-phthalimide by liquid chromatography is determined by the concentration of solid matter.
It was 92.3%, and 97.2% in crystallized crystals.
＜発明の効果＞
本発明によれば、アルカリ水溶液による処理お
よび晶析という極めて簡単な方法により99.5％以
上の高純度のＮ−（シクロヘキシルチオ）−フタル
イミドの取得が可能となつた。<Effects of the Invention> According to the present invention, it has become possible to obtain N-(cyclohexylthio)-phthalimide with a high purity of 99.5% or more by an extremely simple method of treatment with an aqueous alkaline solution and crystallization.
Claims (1)
ドとシクロヘキシルスルフエニルクロライドとを
反応させ、次いで生成反応液中の有機アミンを鉱
酸で中和させて鉱酸塩として水層に移行せしめ、
残る有機溶媒層にアルカリ水溶液を混合させた後
有機溶媒層と水層に分液し、次いで該有機溶媒層
からＮ−（シクロヘキシルチオ）−フタルイミドを
晶析させることを特徴とする高純度Ｎ−（シクロ
ヘキシルチオ）−フタルイミドの製法。1. React phthalimide and cyclohexylsulfenyl chloride in the presence of an organic amine and an organic solvent, then neutralize the organic amine in the reaction solution produced with a mineral acid and transfer it to the aqueous layer as a mineral salt;
High purity N- characterized in that the remaining organic solvent layer is mixed with an aqueous alkali solution, separated into an organic solvent layer and an aqueous layer, and then N-(cyclohexylthio)-phthalimide is crystallized from the organic solvent layer. (Cyclohexylthio)-phthalimide production method.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP60052543A JPS61212559A (en) | 1985-03-18 | 1985-03-18 | Production of high-purity n-(cyclohexylthio)-phthalimide |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP60052543A JPS61212559A (en) | 1985-03-18 | 1985-03-18 | Production of high-purity n-(cyclohexylthio)-phthalimide |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS61212559A JPS61212559A (en) | 1986-09-20 |
| JPH058703B2 true JPH058703B2 (en) | 1993-02-02 |
Family
ID=12917696
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP60052543A Granted JPS61212559A (en) | 1985-03-18 | 1985-03-18 | Production of high-purity n-(cyclohexylthio)-phthalimide |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS61212559A (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR100484384B1 (en) * | 2002-07-24 | 2005-04-20 | 금호타이어 주식회사 | The rubber composition with improvement of process |
-
1985
- 1985-03-18 JP JP60052543A patent/JPS61212559A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS61212559A (en) | 1986-09-20 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US5843923A (en) | Glucosamine sulfate potassium chloride and process of preparation thereof | |
| JP2941287B2 (en) | Process for producing trisodium salt of 2,4,6-trimercapto-S-triazine-9-hydrate | |
| JPH058703B2 (en) | ||
| JPS5829296B2 (en) | Method for producing monomethylhydrazine | |
| US4435576A (en) | Process for the production of 2-amino-4-methyl-benzothiazole | |
| US5382689A (en) | Process for preparation of bevantolol hydrochloride | |
| IL96018A (en) | Process for the preparation of captopril | |
| US5498798A (en) | 4-alkyl-3-chlorobenzenesulfinic acids, 4-alkyl-3-chlorobenzenesulfonylcarboxylic acids, 4-alkyl-3-chloroalkylsulfonylbenzenes and preparation thereof | |
| JPH08291135A (en) | Production of taurine analog | |
| JPH058704B2 (en) | ||
| JP4986343B2 (en) | Method for treating 1-chlorocarbonylpiperidine derivative hydrochloride | |
| KR890000288B1 (en) | Process for preparing guanidino thiazol derivatives | |
| JPH024766A (en) | Synthesis of arylsulfonyl alkylamide | |
| JPS62288102A (en) | Production of dicyanamide metal salt | |
| JPH08268995A (en) | Production of aminoalkylsulfonates | |
| JPH04261189A (en) | Production of tin trifluoromethanesulfonate | |
| EP1124803B1 (en) | Preparation of 3-chloromethylpyridine hydrochloride | |
| JPH10316646A (en) | Production of high-purity crystalline o-methyliso urea acetate and crystalline o-methylisourea acetate obtained by the same | |
| JPS5822140B2 (en) | Production method of β-chloroalanine | |
| JPS629522B2 (en) | ||
| KR100310936B1 (en) | A process for preparing N-(4-methylbenzenesulfonyl)-N'-(3-azabicyclo[3,3,0]octane)urea | |
| JPS6127961A (en) | Preparation of n-substituted phthalimide | |
| JPH0559027A (en) | Preparation of 2-mercaptobenzothiazole | |
| JPS6148818B2 (en) | ||
| SU1544771A1 (en) | Method of producing 1,4,4ъ-triaminodiphenylsulfide |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| LAPS | Cancellation because of no payment of annual fees |