JPH0148902B2 - - Google Patents
Info
- Publication number
- JPH0148902B2 JPH0148902B2 JP12594181A JP12594181A JPH0148902B2 JP H0148902 B2 JPH0148902 B2 JP H0148902B2 JP 12594181 A JP12594181 A JP 12594181A JP 12594181 A JP12594181 A JP 12594181A JP H0148902 B2 JPH0148902 B2 JP H0148902B2
- Authority
- JP
- Japan
- Prior art keywords
- solvent
- chlorophenyl
- reaction
- deoxidizing agent
- amino
- 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
- 239000002904 solvent Substances 0.000 claims description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 12
- JJWKPURADFRFRB-UHFFFAOYSA-N carbonyl sulfide Chemical compound O=C=S JJWKPURADFRFRB-UHFFFAOYSA-N 0.000 claims description 12
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical group [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims description 8
- 239000003795 chemical substances by application Substances 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 7
- -1 (4-chlorophenyl)-2-thiazolidone Chemical compound 0.000 claims description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 230000000895 acaricidal effect Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- TYRGSDXYMNTMML-UHFFFAOYSA-N propyl hydrogen sulfate Chemical compound CCCOS(O)(=O)=O TYRGSDXYMNTMML-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000011282 treatment Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Landscapes
- Thiazole And Isothizaole Compounds (AREA)
Description
【発明の詳細な説明】
本発明はトランス―４―メチル―５―（４―ク
ロロフエニル）―２―チアゾリドン（）の新規
な製造方法に関し、詳しくはエリスロ２―アミノ
―１―（４―クロロフエニル）―プロピル硫酸
（）を溶媒中脱酸剤の存在下、硫化カルボニル
と反応させることを特徴とする製造方法である。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a new method for producing trans-4-methyl-5-(4-chlorophenyl)-2-thiazolidone (2), and more specifically, erythro-2-amino-1-(4-chlorophenyl). - This is a production method characterized by reacting propyl sulfate () with carbonyl sulfide in a solvent in the presence of a deoxidizing agent.
本発明に係る上記化合物（）は優れた殺ダニ
作用を有するトランス―５―（４―クロロフエニ
ル）―３―シクロヘキシルカルバモイル―４―メ
チル―２―チアゾリドンの製造用中間体として有
用な化合物であり文献未記載の新規化合物であ
る。 The above compound () according to the present invention is a compound useful as an intermediate for the production of trans-5-(4-chlorophenyl)-3-cyclohexylcarbamoyl-4-methyl-2-thiazolidone, which has excellent acaricidal activity, and is a reference This is a new, undescribed compound.
本発明方法の実施にあたつては、化合物（）
と、脱酸剤を、溶媒に溶かし、撹拌しながら硫化
カルボニルを吹き込んで反応させる。溶媒として
は化合物（）及び脱酸剤を溶解するものなら何
でもよく例えば水、メタノール、エタノール、テ
トラヒドロフラン、等が使用でき、脱酸剤として
はナトリウムメトキシド、ナトリウムエトキシ
ド、トリエチルアミンカ性ソーダ、等の塩基が使
用できるが、溶媒としてメタノール、脱酸剤とし
てナトリウムメトキシドを用いるのが好ましい。
反応は、室温から溶媒の沸点で１〜10時間行われ
る。反応終了後は溶媒留去、抽出洗浄等通常の後
処理を行つて目的物を得る。 In carrying out the method of the present invention, the compound ()
Then, the deoxidizing agent is dissolved in a solvent, and carbonyl sulfide is blown into the solution while stirring to cause a reaction. Any solvent can be used as long as it dissolves the compound () and the deoxidizing agent, such as water, methanol, ethanol, tetrahydrofuran, etc. As the deoxidizing agent, sodium methoxide, sodium ethoxide, triethylamine caustic soda, etc. can be used. It is preferable to use methanol as the solvent and sodium methoxide as the deoxidizing agent.
The reaction is carried out at room temperature to the boiling point of the solvent for 1 to 10 hours. After the reaction is completed, usual post-treatments such as solvent distillation, extraction and washing are performed to obtain the desired product.
構造はIR，NMR，MASS等のスペクトル測定
結果から決定した。 The structure was determined from spectral measurements such as IR, NMR, and MASS.
原料化合物（）はエリスロ―２―アミノ―１
―（４―クロロフエニル）プロパノールを硫酸と
反応させて製造することができる。 Raw material compound () is erythro-2-amino-1
-(4-chlorophenyl)propanol can be produced by reacting with sulfuric acid.
次に実施例を挙げて本発明の製造法について更
に詳しく説明する。 Next, the manufacturing method of the present invention will be explained in more detail with reference to Examples.
実施例 １
トランス―５―（４―クロロフエニル）―４―
メチル―２―チアゾリドン
エリスロ―２―アミノ―１―（４―クロロフエ
ニル）―プロピル硫酸２ｇをナトリウムメトキシ
ド0.9ｇとメタノール20mlの溶液に溶解し５℃に
て硫化カルボニルを過剰にふき込みそのまま、40
分撹拌を続けた。その後６時間加熱還流した。反
応終了後溶媒を留去し残渣をクロロホルムで抽出
し、水洗後、無水硫酸マグネシウムで乾燥し溶媒
を留去した。残渣をベンゼンにて再結晶して目的
物1.2ｇを得た。収率71％m.p.〔150〜152℃〕
実施例 ２
エタノール30mlに、金属ソーダ0.6ｇを加え、
ナトリウムエトキシドのエタノール溶液を調整
し、ここに、０〜５℃で２―アミノ―１―（４―
クロロフエニル）プロピル硫酸３ｇを加え、次
に、硫化カルボニルを過剰量ふき込んだ。その後
温度を50〜60℃にあげ５時間、反応させた。反応
終了後、溶媒を留去し残渣をクロロホルムに溶解
し、水洗した後、無水硫酸マグネシウムで乾燥し
て、溶媒を留去した。残渣をベンゼンにて再結晶
して目的物1.8ｇを得た。収率70％m.p.〔150〜152
℃〕
実施例 ３
エリスロ―２―アミノ―１―（４―クロロフエ
ニル）プロピル硫酸２ｇを水20mlに懸濁し、０〜
10℃にてトリエチルアミン1.7ｇを加え、次に硫
化カルボニルを反応溶液中に過剰量ふき込んだ。
次に、温度を40℃まで上げそのまま１時間反応さ
せた後、冷却し、析出した結晶を取した。この
結晶をクロロホルムに溶解し水洗した後無水硫酸
マグネシウムで乾燥し、溶媒を留去し、ベンゼン
により再結晶して目的物1.1ｇを得た。収率65％
m.p.〔150〜152℃〕。Example 1 Trans-5-(4-chlorophenyl)-4-
Methyl-2-thiazolidone Dissolve 2 g of erythro-2-amino-1-(4-chlorophenyl)-propyl sulfate in a solution of 0.9 g of sodium methoxide and 20 ml of methanol, and add excess carbonyl sulfide at 5°C.
Stirring was continued for several minutes. Thereafter, the mixture was heated under reflux for 6 hours. After the reaction was completed, the solvent was distilled off, and the residue was extracted with chloroform, washed with water, dried over anhydrous magnesium sulfate, and the solvent was distilled off. The residue was recrystallized from benzene to obtain 1.2 g of the desired product. Yield 71%mp [150-152℃] Example 2 Add 0.6g of metallic soda to 30ml of ethanol,
Prepare an ethanol solution of sodium ethoxide, and add 2-amino-1-(4-
3 g of (chlorophenyl)propyl sulfate was added, and then an excess amount of carbonyl sulfide was bubbled in. Thereafter, the temperature was raised to 50 to 60°C and the reaction was continued for 5 hours. After the reaction was completed, the solvent was distilled off, and the residue was dissolved in chloroform, washed with water, dried over anhydrous magnesium sulfate, and the solvent was distilled off. The residue was recrystallized from benzene to obtain 1.8 g of the desired product. Yield 70% mp [150-152
℃] Example 3 Suspend 2 g of erythro-2-amino-1-(4-chlorophenyl)propyl sulfate in 20 ml of water, and
1.7 g of triethylamine was added at 10°C, and then an excess amount of carbonyl sulfide was sprinkled into the reaction solution.
Next, the temperature was raised to 40°C, and the reaction was continued for 1 hour, then cooled and the precipitated crystals were collected. The crystals were dissolved in chloroform, washed with water, dried over anhydrous magnesium sulfate, the solvent was distilled off, and recrystallized from benzene to obtain 1.1 g of the desired product. Yield 65%
mp [150-152℃].
Claims (1)
エニル）―プロピル硫酸を、溶媒中脱酸剤の存在
下硫化カルボニルと反応させることを特徴とする
トランス―４―メチル―５―（４―クロロフエニ
ル）―２―チアゾリドンの製造方法。 ２ 溶媒がメタノールである特許請求の範囲第１
項記載の製造方法。 ３ 脱酸剤がナトリウムメトキシドである特許請
求の範囲第１又は第２項記載の製造方法。[Claims] 1. Trans-4-methyl-5, characterized in that erythro-2-amino-1-(4-chlorophenyl)-propyl sulfate is reacted with carbonyl sulfide in the presence of a deoxidizing agent in a solvent. - Method for producing (4-chlorophenyl)-2-thiazolidone. 2 Claim 1 in which the solvent is methanol
Manufacturing method described in section. 3. The manufacturing method according to claim 1 or 2, wherein the deoxidizing agent is sodium methoxide.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP12594181A JPS5829777A (en) | 1981-08-13 | 1981-08-13 | Preparation of trans-4-methyl-5-(4-chlorophenyl)-2- thiazolidone |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP12594181A JPS5829777A (en) | 1981-08-13 | 1981-08-13 | Preparation of trans-4-methyl-5-(4-chlorophenyl)-2- thiazolidone |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5829777A JPS5829777A (en) | 1983-02-22 |
| JPH0148902B2 true JPH0148902B2 (en) | 1989-10-20 |
Family
ID=14922755
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP12594181A Granted JPS5829777A (en) | 1981-08-13 | 1981-08-13 | Preparation of trans-4-methyl-5-(4-chlorophenyl)-2- thiazolidone |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5829777A (en) |
-
1981
- 1981-08-13 JP JP12594181A patent/JPS5829777A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5829777A (en) | 1983-02-22 |
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