JPH0460468B2 - - Google Patents
Info
- Publication number
- JPH0460468B2 JPH0460468B2 JP8135585A JP8135585A JPH0460468B2 JP H0460468 B2 JPH0460468 B2 JP H0460468B2 JP 8135585 A JP8135585 A JP 8135585A JP 8135585 A JP8135585 A JP 8135585A JP H0460468 B2 JPH0460468 B2 JP H0460468B2
- Authority
- JP
- Japan
- Prior art keywords
- tetrahydro
- present
- disulfide
- naphthyloxythiocarbonyl
- 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
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
【発明の詳細な説明】 ［産業上の利用分野］ 本発明はジスルフイドに関する。[Detailed description of the invention] [Industrial application field] The present invention relates to disulfides.
本発明化合物であるビス（５，６，７，８−テ
トラヒドロ−２−ナフチルオキシチオカルボニ
ル）ジスフイドは医薬あるいは農薬などに用いる
ことのできる物質への中間体として有用である。 The compound of the present invention, bis(5,6,7,8-tetrahydro-2-naphthyloxythiocarbonyl) disulfide, is useful as an intermediate for substances that can be used in medicines or agricultural chemicals.
［従来の技術］
ビス（５，６，７，８−テトラヒドロ−２−ナ
フチルオキシチオカルボニル）ジスルフイドは文
献未記載の新規化合物である。[Prior Art] Bis(5,6,7,8-tetrahydro-2-naphthyloxythiocarbonyl) disulfide is a new compound that has not been described in any literature.
［発明が解決しようとする問題点］
本発明の目的は、医農薬中間体として有用な新
規化合物であるビス（５，６，７，８−テトラヒ
ドロ−２−ナフチルオキシチオカルボニル）ジス
ルフイドを得ることにある。[Problems to be Solved by the Invention] An object of the present invention is to obtain bis(5,6,7,8-tetrahydro-2-naphthyloxythiocarbonyl) disulfide, which is a new compound useful as a pharmaceutical and agricultural intermediate. It is in.
［問題点を解決するための手段および作用］
本発明者等は、鋭意研究を重ねた結果、本発明
化合物であるビス（５，６，７，８−テトラヒド
ロ−２−ナフチルオキシチオカルボニル）ジスル
フイドの合成に成功し、本発明を完成した。[Means and effects for solving the problems] As a result of intensive research, the present inventors have discovered that bis(5,6,7,8-tetrahydro-2-naphthyloxythiocarbonyl) disulfide, which is a compound of the present invention, has been developed. The present invention was completed by successfully synthesizing the following.
すなわち、本発明は式
で表わされるビス（５，６，７，８−テトラヒド
ロ−２−ナフチルオキシチオカルボニル）ジスル
フイド（以下、本発明化合物という）を提供する
ものである。 That is, the present invention is based on the formula The present invention provides bis(5,6,7,8-tetrahydro-2-naphthyloxythiocarbonyl) disulfide (hereinafter referred to as the compound of the present invention) represented by:
本発明化合物は、５，６，７，８−テトラヒド
ロ−２−ナフトールの金属塩又はアミン塩を二硫
化炭素と反応させキサントゲン酸塩とした後、該
キサントゲン酸塩を沃素等によるハロゲン酸化、
酸素酸化、電解酸化等の酸化法により酸化するこ
とにより合成することができる。 The compound of the present invention is produced by reacting a metal salt or amine salt of 5,6,7,8-tetrahydro-2-naphthol with carbon disulfide to form a xanthate, and then oxidizing the xanthate with halogen using iodine or the like.
It can be synthesized by oxidation using an oxidation method such as oxygen oxidation or electrolytic oxidation.
本反応は溶媒の存在下又は非存在下に実施する
ことができる。溶媒としては、水あるいはペンタ
ン、ヘキサン、ベンゼン、トルエン等の炭化水素
類、アセトン、メチルエチルケトン等のケトン
類、メタノール、エタノール、イソプロパノール
等のアルコール類、ジエチルエーテル、ジメトキ
シエタン、テトラヒドロフラン、ジオキサン等の
エーテル類、アセトニトリル、DMF、DMSO等
極性溶媒等を挙げることができる。 This reaction can be carried out in the presence or absence of a solvent. Examples of solvents include water or hydrocarbons such as pentane, hexane, benzene, and toluene, ketones such as acetone and methyl ethyl ketone, alcohols such as methanol, ethanol, and isopropanol, and ethers such as diethyl ether, dimethoxyethane, tetrahydrofuran, and dioxane. , acetonitrile, DMF, DMSO, and other polar solvents.
［実施例］
以下、本発明を実施例を挙げて詳しく説明す
る。[Example] Hereinafter, the present invention will be explained in detail by giving examples.
実施例 １
ビス（５，６，７，８−テトラヒドロ−２−ナ
フチルオキシチオカルボニル）ジスルフイド2.96
ｇの５，６，７，８−テトラヒドロ−２−ナフト
ールを1.98ｇの苛性カリ水溶液（60ml）に溶解し
た後、5.26ｇの酢酸タリウムを攪拌下室温で加
え、沈殿した５，６，７，８−テトラヒドロ−２
−ナフトールタリウム塩を20mlの二硫化炭素と
200mlのベンゼン中室温で一昼夜反応させ、生成
した対応するキサントゲン酸タリウム塩を別し
た。このキサントゲン酸タリウム塩を20mlのヘキ
サン中室温にて1.27ｇの沃素により酸化した。無
機物を溶液より別し、ヘキサンを減圧下留去し
た。得られた残渣をシリカゲルカラムクロマトグ
ラフイー（ベンゼン：ヘキサン＝１：４）にて精
製し、目的とするビス（５，６，７，８−テトラ
ヒドロ−２−ナフチルオキシチオカルボニル）ジ
スルフイド1.07ｇ（融点90℃−91℃）を得た。Example 1 Bis(5,6,7,8-tetrahydro-2-naphthyloxythiocarbonyl)disulfide 2.96
After dissolving 1.98 g of 5,6,7,8-tetrahydro-2-naphthol in 1.98 g of aqueous caustic potassium solution (60 ml), 5.26 g of thallium acetate was added at room temperature with stirring, and the precipitated 5,6,7,8 -tetrahydro-2
−Naphtholthallium salt with 20ml of carbon disulfide
The reaction was allowed to proceed overnight at room temperature in 200 ml of benzene, and the corresponding xanthate thallium salt produced was separated. The xanthate thallium salt was oxidized with 1.27 g of iodine in 20 ml of hexane at room temperature. Inorganics were separated from the solution, and hexane was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography (benzene:hexane = 1:4) to obtain 1.07 g of the target bis(5,6,7,8-tetrahydro-2-naphthyloxythiocarbonyl) disulfide ( (melting point 90°C-91°C) was obtained.
赤外吸収スペクトル（KBr，cm-1）
2920，1605，1490，
1220，1015
核磁気共鳴スペクトル（CDCl3，δ）
1.48−2.04（4H，ｍ）
2.41−2.98（4H，ｍ）
6.63−7.21（3H，ｍ）
元素分析（C22H22O2S2として
実測値 Ｃ；58.81
Ｈ；4.91
計算値 Ｃ；59.16
Ｈ；4.96
［発明の効果］
本発明に従えば、医農薬中間体として重要な新
規なビス（５，６，７，８−テトラヒドロ−２−
ナフチルオキシチオカルボニル）ジスルフイドが
得られる。 Infrared absorption spectrum (KBr, cm -1 ) 2920, 1605, 1490, 1220, 1015 Nuclear magnetic resonance spectrum (CDCl3, δ) 1.48−2.04 (4H, m) 2.41−2.98 (4H, m) 6.63−7.21 (3H , m) Elemental analysis (as C 22 H 22 O 2 S 2 Actual value C; 58.81 H; 4.91 Calculated value C; 59.16 H; 4.96 [Effects of the invention] According to the present invention, important novelties as medicinal and agricultural intermediates have been achieved. bis(5,6,7,8-tetrahydro-2-
Naphthyloxythiocarbonyl) disulfide is obtained.
本発明化合物を塩素、スルフリルクロライド等
を用いて塩素化分解することにより、医農薬中間
体として重要な０−５，６，７，８−テトラヒド
ロ−２−ナフチル クロロチオホルメートを得る
ことができる。 By chlorinating and decomposing the compound of the present invention using chlorine, sulfuryl chloride, etc., 0-5,6,7,8-tetrahydro-2-naphthyl chlorothioformate, which is important as a pharmaceutical and agricultural intermediate, can be obtained. .
Claims (1)
ラヒドロ−２−ナフチルオキシチオカルボニル）
ジスルフイド。1 Bis(5,6,7,8-tetrahydro-2-naphthyloxythiocarbonyl) represented by the formula
Disulfide.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP8135585A JPS61243061A (en) | 1985-04-18 | 1985-04-18 | Disulfide |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP8135585A JPS61243061A (en) | 1985-04-18 | 1985-04-18 | Disulfide |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS61243061A JPS61243061A (en) | 1986-10-29 |
| JPH0460468B2 true JPH0460468B2 (en) | 1992-09-28 |
Family
ID=13744044
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP8135585A Granted JPS61243061A (en) | 1985-04-18 | 1985-04-18 | Disulfide |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS61243061A (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103130693A (en) * | 2013-03-12 | 2013-06-05 | 兰州精细化工高新技术开发公司 | Method for synthesizing bis-iso-propyl xanthogenat by using hydrogen peroxide |
-
1985
- 1985-04-18 JP JP8135585A patent/JPS61243061A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS61243061A (en) | 1986-10-29 |
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