JPH0613469B2 - 5-Amino-2-chlorobenzenethiol and process for producing the same - Google Patents
5-Amino-2-chlorobenzenethiol and process for producing the sameInfo
- Publication number
- JPH0613469B2 JPH0613469B2 JP365785A JP365785A JPH0613469B2 JP H0613469 B2 JPH0613469 B2 JP H0613469B2 JP 365785 A JP365785 A JP 365785A JP 365785 A JP365785 A JP 365785A JP H0613469 B2 JPH0613469 B2 JP H0613469B2
- Authority
- JP
- Japan
- Prior art keywords
- chlorobenzenethiol
- amino
- producing
- same
- compound
- 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
Landscapes
- Indole 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】 本発明は、５−アミノ−２−クロロベンゼンチオール
（以下、本発明化合物と記す。）およびその製造法に関
するものである。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to 5-amino-2-chlorobenzenethiol (hereinafter referred to as the compound of the present invention) and a method for producing the same.
本発明化合物を、一般式 Ｘ−CH2COOH 〔Ｉ〕 〔式中、Ｘは塩素原子、臭素原子または沃素原子を表わ
す。〕 で示されるハロ酢酸と反応させ、次いで３，４，５，６
−テトラヒドロフタル酸無水物と反応させた後、一般式 Ｒ−ＯＨ 〔II〕 〔式中、Ｒは低級アルキル基、低級ハロアルキル基また
は低級シクロアルキル基を表わす。〕 で示されるアルコール類と反応させることによって製造
することができる一般式 〔式中、Ｒは前記と同じ意味を表わす。〕 で示されるテトラヒドロフタルイミド誘導体は、ダイ
ズ、トウモロコシ、コムギ、イネ等の主要作物に対して
問題となる薬害を示さず、且つ、多くの雑草に対して充
分な除草効力を有する（特開昭６０−５４３６２号）。The compound of the present invention is represented by the general formula X-CH 2 COOH [I] [wherein, X represents a chlorine atom, a bromine atom or an iodine atom. ] It is made to react with haloacetic acid represented by
-After reacting with tetrahydrophthalic anhydride, it has the general formula R-OH [II] [wherein R represents a lower alkyl group, a lower haloalkyl group or a lower cycloalkyl group. ] A general formula which can be produced by reacting with an alcohol represented by [In the formula, R represents the same meaning as described above. ] The tetrahydrophthalimide derivative represented by the following does not show a harmful phytotoxicity to major crops such as soybean, corn, wheat and rice, and has a sufficient herbicidal effect against many weeds (Japanese Patent Laid-Open No. Sho 60-60). -54362).
本発明化合物は、標準的には２−クロロ−５−ニトロベ
ンゼンスルホニルクロリドと、これに対して６〜２０当
量、好ましくは６〜１２当量の塩化第一錫、亜鉛等の金
属還元剤とを溶媒中、４０℃〜１０５℃、好ましくは８
０℃〜１０５℃で、瞬時〜１０時間反応させることによ
って製造することができる。The compound of the present invention typically comprises 2-chloro-5-nitrobenzenesulfonyl chloride as a solvent and 6 to 20 equivalents, preferably 6 to 12 equivalents, of a metal reducing agent such as stannous chloride or zinc. Medium, 40 ° C to 105 ° C, preferably 8
It can be produced by reacting at 0 ° C to 105 ° C for an instant to 10 hours.
溶媒としては、塩化第一錫の場合は塩酸、亜鉛の場合は
塩酸もしくは希硫酸があげられる。Examples of the solvent include hydrochloric acid in the case of stannous chloride and hydrochloric acid or diluted sulfuric acid in the case of zinc.
反応終了後の反応液は、必要に応じ、濃塩酸等の酸を加
え、生じた結晶を別する等の通常の後処理を行い、必
要ならば、クロマトグラフィー、再結晶等の操作によ
り、精製することによって、目的の本発明化合物を得る
ことができる。After completion of the reaction, the reaction solution is subjected to usual post-treatment such as adding an acid such as concentrated hydrochloric acid and separating the generated crystals, if necessary, and purified by a procedure such as chromatography and recrystallization. By doing so, the desired compound of the present invention can be obtained.
なお、原料化合物である２−クロロ−５−ニトロベンゼ
ンスルホニルクロリドは、Ｐ．Ｆｉｓｃｈｅｒ，Ｃｈｅ
ｍ． Ｂｅｒ．，２４ ３１９４（１８９１）に記載さ
れている公知化合物である。In addition, 2-chloro-5-nitrobenzenesulfonyl chloride, which is a raw material compound, was prepared as described in P. Fischer, Che
m. Ber. , 24 3194 (1891).
次に本発明化合物の製造例を示す。Next, production examples of the compound of the present invention will be shown.
製造例 無水塩化第一錫１６１ｇを濃塩酸１６０mlに溶かし、０
℃で徐々に２−クロロ−５−ニトロベンゼンスルホニル
クロリド３４ｇを加えた。その後、昇温し、１００℃で
１５分間加熱した。反応混合物が冷えてから濃塩酸２４
０mlを加え、析出した結晶を取した。この結晶を重曹
水で中和し、酢酸エチルで抽出した。抽出液を乾燥、濃
縮し、５−アミノ−２−クロロベンゼンチオール２１ｇ
を得た。NMR(CDCl3+D6-DMSO)δppm4.0(3H,br.s,NH 2,SH)
6.3〜6.7(2H,m)、6.8〜7.1(1H,m) 核磁気共鳴スペクトル−図１に示す通り。Production Example 161 g of anhydrous stannous chloride was dissolved in 160 ml of concentrated hydrochloric acid,
34 g of 2-chloro-5-nitrobenzenesulphonyl chloride was slowly added at 0 ° C. After that, the temperature was raised and heated at 100 ° C. for 15 minutes. After the reaction mixture has cooled, concentrated hydrochloric acid 24
0 ml was added and the precipitated crystals were collected. The crystals were neutralized with aqueous sodium hydrogen carbonate and extracted with ethyl acetate. The extract is dried and concentrated to give 21 g of 5-amino-2-chlorobenzenethiol.
Got NMR (CDCl 3 + D 6 -DMSO ) δppm4.0 (3H, br.s, N H 2, S H)
6.3-6.7 (2H, m), 6.8-7.1 (1H, m) Nuclear magnetic resonance spectrum-as shown in FIG.
図１は製造例で得られた５−アミノ−２−クロロベンゼ
ンチオールの核磁気共鳴スペクトルである。 図１中、横軸はケミカルシフトを、縦軸は共鳴強度を表
わす。FIG. 1 is a nuclear magnetic resonance spectrum of 5-amino-2-chlorobenzenethiol obtained in Production Example. In FIG. 1, the horizontal axis represents the chemical shift and the vertical axis represents the resonance intensity.
Claims (2)
ル。1. 5-Amino-2-chlorobenzenethiol.
ルクロリドと金属還元剤とを反応させることを特徴とす
る５−アミノ−２−クロロベンゼンチオールの製造法。2. A method for producing 5-amino-2-chlorobenzenethiol, which comprises reacting 2-chloro-5-nitrobenzenesulfonyl chloride with a metal reducing agent.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP365785A JPH0613469B2 (en) | 1985-01-11 | 1985-01-11 | 5-Amino-2-chlorobenzenethiol and process for producing the same |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP365785A JPH0613469B2 (en) | 1985-01-11 | 1985-01-11 | 5-Amino-2-chlorobenzenethiol and process for producing the same |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS61161256A JPS61161256A (en) | 1986-07-21 |
| JPH0613469B2 true JPH0613469B2 (en) | 1994-02-23 |
Family
ID=11563535
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP365785A Expired - Lifetime JPH0613469B2 (en) | 1985-01-11 | 1985-01-11 | 5-Amino-2-chlorobenzenethiol and process for producing the same |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0613469B2 (en) |
-
1985
- 1985-01-11 JP JP365785A patent/JPH0613469B2/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| JPS61161256A (en) | 1986-07-21 |
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