JPS5835991B2 - N-substituted bisanilinodisulfide derivative and method for producing the derivative - Google Patents
N-substituted bisanilinodisulfide derivative and method for producing the derivativeInfo
- Publication number
- JPS5835991B2 JPS5835991B2 JP8407280A JP8407280A JPS5835991B2 JP S5835991 B2 JPS5835991 B2 JP S5835991B2 JP 8407280 A JP8407280 A JP 8407280A JP 8407280 A JP8407280 A JP 8407280A JP S5835991 B2 JPS5835991 B2 JP S5835991B2
- Authority
- JP
- Japan
- Prior art keywords
- derivative
- bisanilinodisulfide
- substituted
- disulfide
- bis
- 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
Landscapes
- Compositions Of Macromolecular Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Description
【発明の詳細な説明】
この発明は、新規な化学構造を有するＮ−置換ビスアニ
リノジスルフィド誘導体及びその誘導体＊＊の製造方法
に関する。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to an N-substituted bisanilinodisulfide derivative having a novel chemical structure and a method for producing the derivative**.
この発明に係る新規なＮ−置換ビスアニリノジスルフィ
ド誘導体は、農園芸用殺菌剤、種々の農薬中間体、ゴム
用添加剤及びその中間体並びに種種の工業用薬剤の中間
体として有用な化合物である。The novel N-substituted bisanilinodisulfide derivatives according to the present invention are useful compounds as agricultural and horticultural fungicides, various agricultural chemical intermediates, rubber additives and their intermediates, and various industrial drug intermediates. be.
この発明の要旨は、
■、一般式
〔ただし、式中のＲは炭素数１〜４のアルキル基２５※
で示される２
・２′
ビスアニリノジスルフィ
ド※
〔ただし、式中のＲは炭素数１〜４のアルキル基を表す
。The gist of this invention is as follows: (1) General formula [However, R in the formula is a 2-2' bisanilinodisulfide* represented by an alkyl group having 1 to 4 carbon atoms 25* [However, R in the formula is a carbon number Represents 1 to 4 alkyl groups.
〕で示されるＮ−置換ビスアニリノジスルフィド誘導体
の製造方法である。] is a method for producing an N-substituted bisanilinodisulfide derivative.
この発明の構成要素を具体的に述べる。The components of this invention will be specifically described.
この発明に係るＮ−置換ビスアニリノジスルフィド誘導
体の代表的なものは、２・２−ビス（メトキシカルボニ
ルチオウレイドフェニル）ジスルフィド、２・２−ビス
（エトキシカルボニルチオウレイドフェニル）ジスルフ
ィド、２・２−ビス＊＊（イソプロポキシカルボニルチ
オウレイドフェニル）ジスルフィド、２・２′−ビス（
ブトキシカルボニルチオウレイドフェニル）ジスルフィ
ドであるが、この発明においてはこれらに限定されるも
のではない。Representative examples of the N-substituted bisanilinodisulfide derivatives according to the present invention include 2,2-bis(methoxycarbonylthioureidophenyl)disulfide, 2,2-bis(ethoxycarbonylthioureidophenyl)disulfide, and 2,2-bis(methoxycarbonylthioureidophenyl)disulfide. -bis**(isopropoxycarbonylthioureidophenyl)disulfide, 2,2'-bis(
butoxycarbonylthioureidophenyl) disulfide, but the present invention is not limited thereto.
この発明に係るＮ−置換ビスアニリノジスルフィド誘導
体は、２・２−ビスアニリノジスルフィドとイソチオシ
アナトギ酸アルキル類とから、下記の反応式に従って製
造される。The N-substituted bisanilinodisulfide derivative according to the present invention is produced from 2,2-bisanilinodisulfide and an alkyl isothiocyanatoformate according to the reaction formula below.
〔ただし、式中、Ｒは炭素数１〜４のアルキル基を表わ
す。[However, in the formula, R represents an alkyl group having 1 to 4 carbon atoms.
〕こノ発明に係るＮ−置換ビスアニリノジスルフィド誘
導体は、新規化合物であって、下記の製造方法に準拠し
て造られる。] The N-substituted bisanilinodisulfide derivative according to the present invention is a new compound, and is produced according to the production method described below.
この発明に係る製造方法は、１モル当量の２・２′−ビ
スアニリノジスルフィドを所定量のアセトン・酢酸エチ
ル・アセトニトリルのごとき不活性極性溶媒中に溶解せ
しめ、その溶液を１０℃以下の温度に保ち、その中に、
２モル当量のインチオシアナトギ酸アルキル類を所定量
の同種溶媒に溶解した溶液を約１時間かげて滴下する。The production method according to the present invention involves dissolving 1 molar equivalent of 2,2'-bisanilinodisulfide in a predetermined amount of an inert polar solvent such as acetone, ethyl acetate, or acetonitrile, and maintaining the solution at a temperature of 10°C or less. and within it,
A solution of 2 molar equivalents of alkyl inthiocyanatoformate dissolved in a predetermined amount of the same solvent is added dropwise over about 1 hour.
滴下終了後、反応温度Ｏ〜８０℃好ましくは１０〜５０
℃にて３〜４時間かくはんしながら反応せしめる。After completion of the dropwise addition, the reaction temperature is 0 to 80°C, preferably 10 to 50°C.
The reaction is allowed to proceed at a temperature of 3 to 4 hours with stirring.
反応終了後冷却して結晶を析出せしめ、生成した結晶を
吸引１過し、所定量の水で洗浄後乾燥して目的物である
この発明のＮ−置換ビスアニリノジスルフィド誘導体を
得るのである。After the reaction is completed, the reaction mixture is cooled to precipitate crystals, and the resulting crystals are filtered under suction, washed with a predetermined amount of water, and dried to obtain the target product, the N-substituted bisanilinodisulfide derivative of the present invention.
次に、実施例によってこの発明を具体的に説明するが、
この発明は、これらに記載された事項に限定されるもの
ではない。Next, this invention will be specifically explained with reference to Examples.
This invention is not limited to the matters described above.
実施例 １
２・２−ビス（メトキシカルボニルチオウレイドフェニ
ル）ジスルフィドの製造
２・２′−ビスアニリノジスルフィド１２．．４ｆを酢
酸エチル２００ＴＬｌに溶解する。Example 1 Preparation of 2,2-bis(methoxycarbonylthioureidophenyl)disulfide 2,2'-bisanilinodisulfide12. ．． 4f is dissolved in 200 TLl of ethyl acetate.
この溶液を１０℃以下の温度に保ち、その中に、イソチ
オシアナトギ酸メチル１２．３ｆを酢酸エチル５０１ｒ
Ｌｌに溶解した溶液を１時間かげて滴下する。This solution was kept at a temperature below 10°C, and 12.3f of methyl isothiocyanatoformate was added to 501r of ethyl acetate.
A solution dissolved in Ll is added dropwise over a period of 1 hour.
滴下終了後３０℃に昇温しで同温度で３時間かくはんし
ながら反応を行う。After completion of the dropwise addition, the temperature was raised to 30°C, and the reaction was carried out at the same temperature for 3 hours while stirring.
反応終了後冷却して結晶を析出せしめ、その析出の完了
をまって結晶を吸引濾過し、水１００ｒｒＬｌで洗浄し
た後、乾燥して目的物の２・２′−ビス（メトキシカル
ボニルチオウレイドフェニル）ジスルフィドを得た。After completion of the reaction, it is cooled to precipitate crystals, and after waiting for the completion of the precipitation, the crystals are suction-filtered, washed with 100 rrL of water, and dried to obtain the target product, 2,2'-bis(methoxycarbonylthioureidophenyl). Obtained disulfide.
収量２１．５Ｓ’（収率８９．２％）。Yield 21.5S' (yield 89.2%).
このものの特性値及び同定値は下記のとおりである。The characteristic values and identification values of this product are as follows.
外 観 淡黄色結晶
融 点 ２２１℃（分解）
元素分析
Ｃ（％） Ｈ（％） Ｎ（％） Ｓ（％）実測値
４４．６０３．９０１１．６５２５．４０計算値 ４４
．８０３．７６１１−６１２６．５７実施例 ２
２・２−ビス（エトキシカルボニルチオウレイドフェニ
ル）ジスルフィドの製造
２・２′−ビスアニリノジスルフィド１２．４ｆ？を酢
酸エチル１８０７７１１に溶解する。Appearance Pale yellow crystal Melting point 221℃ (decomposition) Elemental analysis C (%) H (%) N (%) S (%) Actual value
44.603.9011.6525.40 Calculated value 44
．． 803.7611-6126.57 Example 2 Preparation of 2,2-bis(ethoxycarbonylthioureidophenyl)disulfide 2,2'-bisanilinodisulfide 12.4f? is dissolved in 1807711 ethyl acetate.
この溶液を１０℃以下の温度に保ち、その中に、インチ
オシアナトギ酸エチル１３．’ｌを酢酸エチル５０ｍＡ
に溶解した溶液を１時間かけて滴下する。This solution is kept at a temperature below 10° C. and contains 13.0% ethyl inthiocyanatoformate. 'l ethyl acetate 50mA
A solution dissolved in is added dropwise over 1 hour.
滴下終了後３０℃に昇温して同温度で３時間かくはんし
ながら反応を行う。After the dropwise addition is completed, the temperature is raised to 30°C, and the reaction is carried out at the same temperature for 3 hours while stirring.
次に実施例１と同様に処理して目的物の２・２′−ビス
（エトキシカルボニルチオウレイドフェニル）ジスルフ
ィドを得た。Next, the same treatment as in Example 1 was carried out to obtain the desired product, 2,2'-bis(ethoxycarbonylthiouridophenyl)disulfide.
収量２３、（１（収率９０．２％）。Yield 23, (1 (yield 90.2%).
このものの特性値及び同定値は下記のとおりである。The characteristic values and identification values of this product are as follows.
外 観 淡黄色結晶
融点Ｑｏ７．ｏ〜２０９．５℃
元素分析
Ｃ（％） Ｈ（％） Ｎ（％） Ｓ（％）実測値
４８．８８４．３４１１．１１２５．０５計算値 ４７
．０４４．３４１０．９７２５．１１実施例 ３
２・２′〜ビス（イソプロポキシカルボニルチオウレイ
ドフェニル）ジスルフィドの製造
２・２′−ビスアニリノジスルフィド１２．４ｆを酢酸
エチル１８０ｍ１に溶解する。Appearance Pale yellow crystal Melting point Qo7. o~209.5℃ Elemental analysis C (%) H (%) N (%) S (%) Actual value
48.884.3411.1125.05 Calculated value 47
．． 044.3410.9725.11 Example 3 Preparation of 2,2'-bis(isopropoxycarbonylthioureidophenyl) disulfide 12.4 f of 2,2'-bisanilinodisulfide are dissolved in 180 ml of ethyl acetate.
この溶液を１０℃以下の温度に保ち、その中に、インチ
オシアナトギ酸イソプロピル１５．２Ｐを酢酸エチル５
０ｒＩｌｌに溶解した溶液を１時間かげて滴下する。This solution is kept at a temperature below 10°C, and 15.2P of isopropyl inthiocyanatoformate is added to 5.2P of ethyl acetate.
A solution dissolved in 0rIll is added dropwise over a period of 1 hour.
滴下終了後５０℃に昇温しで同温度で４時間かくはんし
ながら反応を行う。After completion of the dropwise addition, the temperature was raised to 50°C, and the reaction was carried out at the same temperature for 4 hours while stirring.
次に実施例１と同様に処理して目的物の２・２′−ビス
（インプロポキシカルボニルチオウレイドフェニル）ジ
スルフィドを得た。Next, the product was treated in the same manner as in Example 1 to obtain the desired product, 2,2'-bis(impropoxycarbonylthiouridophenyl)disulfide.
収量２４．（１（収率８９．２％）。Yield 24. (1 (yield 89.2%).
このものの特性値及び同定値は下記のとおりである。The characteristic values and identification values of this product are as follows.
外 観 淡黄色結晶
融点１８８．５〜１９０．０℃
元素分析
Ｃ（％） Ｈ（％）Ｎ（％） Ｓ（％）実測値 ４
８．８０４．８２１０．５５２３．７６計算値 ４９．
０５４．８６１０．４０２３．８０実施例 ４
２・２′−ビス（ブトキシカルボニルチオウレイドフェ
ニル）ジスルフィドの製造
２・２′−ビスアニリノジスルフィド１２．４ノをアセ
トン１８０ｍ１に溶解する。Appearance Pale yellow crystal Melting point 188.5-190.0°C Elemental analysis C (%) H (%) N (%) S (%) Actual value 4
8.804.8210.5523.76 Calculated value 49.
054.8610.4023.80 Example 4 Preparation of 2,2'-bis(butoxycarbonylthioureidophenyl) disulfide 12.4 parts of 2,2'-bisanilinodisulfide are dissolved in 180 ml of acetone.
この溶液を５℃以下の温度に保ち、その中に、イソチオ
シアナトギ酸ブチル１６．７？をアセトン３０ｒｒＬｌ
に溶解した溶液を１時間かげて滴下する。This solution is kept at a temperature below 5°C and contains 16.7% butyl isothiocyanatoformate. acetone 30rrLl
Add the solution dissolved in water dropwise for 1 hour.
滴下終了後３０℃に昇温しで同温度で３時間かくはんし
ながら反応を行う。After completion of the dropwise addition, the temperature was raised to 30°C, and the reaction was carried out at the same temperature for 3 hours while stirring.
次に実施例１と同様に処理して目的物の２・２′−ビス
（ブトキシカルボニルチオウレイドフェニル）ジスルフ
ィドを得た。Next, the same treatment as in Example 1 was carried out to obtain the desired product, 2,2'-bis(butoxycarbonylthiouridophenyl)disulfide.
収量２３．Ｏｒ（収率８８．５％）。Yield 23. Or (yield 88.5%).
このものの特性値及び同定値は下記のとおりである。The characteristic values and identification values of this product are as follows.
外 観 淡黄色結晶 融点１５８．４〜１６１．２℃ 元素分析Appearance Pale yellow crystal Melting point 158.4-161.2℃ elemental analysis
Claims (1)
。 〕で示されるＮ−置換ビスアニリノジスルフィド誘導体
。 ２ 一般式 ％式％ 〔ただし、式中のＲは炭素数１〜４のアルキル基を表す
。 〕で示されるインチオシアナトギ酸アルキル類とを反応
せしめることを特徴とする 特許 〔ただし、式中のＲは炭素数１〜４のアルキル基を表す
。 〕で示されるＮ−置換ビスアニリノジスルフィド誘導体
の製造方法。[Claims] 1 General formula [However, R in the formula represents an alkyl group having 1 to 4 carbon atoms. ] N-substituted bisanilinodisulfide derivative. 2 General formula % formula % [However, R in the formula represents an alkyl group having 1 to 4 carbon atoms. [However, R in the formula represents an alkyl group having 1 to 4 carbon atoms. ] A method for producing an N-substituted bisanilinodisulfide derivative.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP8407280A JPS5835991B2 (en) | 1980-06-23 | 1980-06-23 | N-substituted bisanilinodisulfide derivative and method for producing the derivative |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP8407280A JPS5835991B2 (en) | 1980-06-23 | 1980-06-23 | N-substituted bisanilinodisulfide derivative and method for producing the derivative |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS579759A JPS579759A (en) | 1982-01-19 |
| JPS5835991B2 true JPS5835991B2 (en) | 1983-08-05 |
Family
ID=13820277
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP8407280A Expired JPS5835991B2 (en) | 1980-06-23 | 1980-06-23 | N-substituted bisanilinodisulfide derivative and method for producing the derivative |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5835991B2 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS59106238A (en) * | 1982-12-13 | 1984-06-19 | 株式会社 大里商店 | Press broken rice hull |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS60179466A (en) * | 1984-02-24 | 1985-09-13 | Toyo Alum Kk | Highly heat-resistant corrosion-resistant pigment composition |
| EP1368309B2 (en) | 2001-02-22 | 2014-10-01 | Anika Therapeutics Inc. | Thiol-modified hyaluronan |
-
1980
- 1980-06-23 JP JP8407280A patent/JPS5835991B2/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS59106238A (en) * | 1982-12-13 | 1984-06-19 | 株式会社 大里商店 | Press broken rice hull |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS579759A (en) | 1982-01-19 |
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