JPH0532629A - Production of highly pure methyl carbamate - Google Patents
Production of highly pure methyl carbamateInfo
- Publication number
- JPH0532629A JPH0532629A JP21047291A JP21047291A JPH0532629A JP H0532629 A JPH0532629 A JP H0532629A JP 21047291 A JP21047291 A JP 21047291A JP 21047291 A JP21047291 A JP 21047291A JP H0532629 A JPH0532629 A JP H0532629A
- Authority
- JP
- Japan
- Prior art keywords
- naphthyl
- tetrahydro
- methoxy
- pyridyl
- methylthiocarbamate
- 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.)
- Granted
Links
Landscapes
- Pyridine Compounds (AREA)
Abstract
Description
【０００１】[0001]
【産業上の利用分野】本発明は純度９９．９％以上のＯ
−（５，６，７，８−テトラヒドロ−２−ナフチル）Ｎ
−（６−メトキシ−２−ピリジル）−Ｎ−メチルチオカ
−バメイトの簡便な製造法に関する。本発明の製造方法
により製造することができるＯ−（５，６，７，８−テ
トラヒドロ−２−ナフチル）Ｎ−（６−メトキシ−２−
ピリジル）−Ｎ−メチルチオカーバメイトは、医薬品と
して有用な化合物である。BACKGROUND OF THE INVENTION The present invention relates to O having a purity of 99.9% or more.
-(5,6,7,8-tetrahydro-2-naphthyl) N
The present invention relates to a simple method for producing-(6-methoxy-2-pyridyl) -N-methylthiocarbamate. O- (5,6,7,8-tetrahydro-2-naphthyl) N- (6-methoxy-2- that can be produced by the production method of the present invention.
Pyridyl) -N-methylthiocarbamate is a compound useful as a medicine.
【０００２】[0002]
【従来の技術】Ｏ−（５，６，７，８−テトラヒドロ−
２−ナフチル）Ｎ−（６−メトキシ−２−ピリジル）Ｎ
−メチルチオカーバメイトは、Ｏ−（５，６，７，８−
テトラヒドロ−２−ナフチル）−クロロチオホルメイト
と２−メトキシ−６−メチルアミノピリジンを脱ハロゲ
ン化水素剤存在下で反応させ、得られた粗製物は、エタ
ノール、イソプロピルアルコール等のＣ1 〜Ｃ3 のアル
コールを用いて洗浄後、水洗し、Ｃ1 〜Ｃ3 のアルコー
ル及びｎ−ヘキサンンから活性炭を用い再結晶すること
により該チオカーバメイトを精製できることは公知であ
る。2. Description of the Related Art O- (5,6,7,8-tetrahydro-
2-naphthyl) N- (6-methoxy-2-pyridyl) N
-Methylthiocarbamate is O- (5,6,7,8-
Tetrahydro-2-naphthyl) -chlorothioformate and 2-methoxy-6-methylaminopyridine are reacted in the presence of a dehydrohalogenating agent, and the obtained crude product is C 1 -C such as ethanol or isopropyl alcohol. after washing with 3 alcohol, washed with water, it is known that can purify the thio carbamate by recrystallization using activated carbon from alcohol and n- Hekisan'n of C 1 -C 3.
【０００３】[0003]
【本発明が解決しようとする課題】しかし、この方法で
得られた該カーバメイトの純度は、通常、純度は９９．
７％程度であり、それ以上の純度の該チオカーバメイト
を得るためにはＣ1 〜Ｃ3 のアルコール又はｎ−ヘキサ
ン等の炭化水素を用い、再度、再結晶を繰り返さなけれ
ばならない。従って、粗製Ｏ−（５，６，７，８−テト
ラヒドロ−２−ナフチル）Ｎ−（６−メトキシ−２−ピ
リジル）−Ｎ−メチルチオカーバメイトからの簡便な純
度９９．９％以上の高純度チオカーバメイトの製造方法
が望まれている。However, the purity of the carbamate obtained by this method is usually 99.
In order to obtain the thiocarbamate having a purity of about 7% or more, a C 1 -C 3 alcohol or a hydrocarbon such as n-hexane must be used and recrystallization must be repeated. Therefore, a simple high purity thiol of 99.9% or more from crude O- (5,6,7,8-tetrahydro-2-naphthyl) N- (6-methoxy-2-pyridyl) -N-methylthiocarbamate was obtained. A method for producing carbamate is desired.
【０００４】[0004]
【課題を解決するための手段】本発明の目的は高純度の
Ｏ−（５，６，７，８−テトラヒドロ−２−ナフチル）
Ｎ−（６−メトキシ−２−ピリジル）−Ｎ−メチルチオ
カーバメイトを簡便に得ることである。The object of the present invention is to provide highly pure O- (5,6,7,8-tetrahydro-2-naphthyl).
The purpose is to obtain N- (6-methoxy-2-pyridyl) -N-methylthiocarbamate easily.
【０００５】本発明者らは、粗製Ｏ−（５，６，７，８
−テトラヒドロ−２−ナフチル）Ｎ−（６−メトキシ−
２−ピリジル）−Ｎ−メチルチオカーバメイトから簡便
に高純度の該チオカーバメイトを得る方法について鋭意
検討した結果、粗製Ｏ−（５，６，７，８−テトラヒド
ロ−２−ナフチル）Ｎ−（６−メトキシ−２−ピリジ
ル）−Ｎ−メチルチオカーバメイトを含水率２０〜７０
％に調製し活性炭を加えてＣ1 〜Ｃ3 のアルコールから
再結晶することにより高純度Ｏ−（５，６，７，８−テ
トラヒドロ−２−ナフチル）Ｎ−（６−メトキシ−２−
ピリジル）−Ｎ−メチルチオカーバメイトを製造できる
ことを見出し本発明を完成した。The present inventors have found that crude O- (5,6,7,8
-Tetrahydro-2-naphthyl) N- (6-methoxy-
As a result of diligent studies on a method for easily obtaining high-purity thiocarbamate from 2-pyridyl) -N-methylthiocarbamate, crude O- (5,6,7,8-tetrahydro-2-naphthyl) N- (6- Methoxy-2-pyridyl) -N-methylthiocarbamate having a water content of 20 to 70
% O- (5,6,7,8-tetrahydro-2-naphthyl) N- (6-methoxy-2-) was prepared by recrystallization from C 1 -C 3 alcohol by adding activated carbon.
The present invention has been completed by finding that pyridyl) -N-methylthiocarbamate can be produced.
【０００６】即ち本発明は、Ｏ−（５，６，７，８−テ
トラヒドロ−２−ナフチル）−クロロチオホルメイトと
２−メトキシ−６−メチルアミノピリジンを脱ハロゲン
化水素剤存在下、含水イソプロピルアルコール溶媒中で
縮合して得られた粗製Ｏ−（５，６，７，８−テトラヒ
ドロ−２−ナフチル）Ｎ−（６−メトキシ−２−ピリジ
ル）−Ｎ−メチルチオカーバメイトをＣ1 〜Ｃ3 アルコ
ールおよび水を用いて洗浄後、該チオカーバメイトの含
水率を２０〜７０％に調製し活性炭を加えてＣ 1 〜Ｃ3
アルコールで再結晶することにより高純度Ｏ−（５，
６，７，８−テトラヒドロ−２−ナフチル）Ｎ−（６−
メトキシ−２−ピリジル）−Ｎ−メチルチオカーバメイ
トの製造方法を提供するものである。That is, the present invention is directed to O- (5,6,7,8-te
With trahydro-2-naphthyl) -chlorothioformate
Dehalogenation of 2-methoxy-6-methylaminopyridine
In a hydrous isopropyl alcohol solvent in the presence of a hydrogenating agent
Crude O- (5,6,7,8-tetrahyde obtained by condensation
Doro-2-naphthyl) N- (6-methoxy-2-pyridy
) -N-methylthiocarbamate to C1~ C3Arco
And thiocarbamate after washing with water and water.
Adjust the water rate to 20-70% and add activated carbon to add C 1~ C3
High purity O- (5,
6,7,8-Tetrahydro-2-naphthyl) N- (6-
Methoxy-2-pyridyl) -N-methylthiocarbamei
The present invention provides a method for manufacturing a grate.
【０００７】[0007]
【作用】以下、本発明について詳細に説明する。The present invention will be described in detail below.
【０００８】粗製Ｏ−（５，６，７，８−テトラヒドロ
−２−ナフチル）Ｎ−（６−メトキシ−２−ピリジル）
−Ｎ−メチルチオカーバメイトは、Ｏ−（５，６，７，
８−テトラヒドロ−２−ナフチル）−クロロチオホルメ
イトと２−メトキシ−６−メチルアミノピリジンとを脱
ハロゲン化水素剤存在下、イソプロピルアルコールと水
との混合溶媒系中、縮合することにより得ることができ
る。この粗製Ｏ−（５，６，７，８−テトラヒドロ−２
−ナフチル）Ｎ−（６−メトキシ−２−ピリジル）−Ｎ
−メチルチオカーバメイトをろ過などにより分離した後
に、更にＣ1 〜Ｃ3 アルコールおよび水を用いて洗浄
後、該チオカーバメイトの含水率を２０〜７０％に調製
し活性炭を加えてＣ1 〜Ｃ3 アルコールで再結晶するこ
とにより純度９９．９％以上の目的物を得る。Crude O- (5,6,7,8-tetrahydro-2-naphthyl) N- (6-methoxy-2-pyridyl)
-N-methylthiocarbamate is O- (5,6,7,
Obtained by condensing 8-tetrahydro-2-naphthyl) -chlorothioformate and 2-methoxy-6-methylaminopyridine in the presence of a dehydrohalogenating agent in a mixed solvent system of isopropyl alcohol and water. You can This crude O- (5,6,7,8-tetrahydro-2
-Naphthyl) N- (6-methoxy-2-pyridyl) -N
- methylthio Carver mate after separation by such as filtration, further C 1 -C 3 alcohol and washed with water, the thio carbamate C 1 with addition of active charcoal was prepared water content 20 to 70% of the -C 3 alcohol The desired product having a purity of 99.9% or more is obtained by recrystallization from.
【０００９】粗製Ｏ−（５，６，７，８−テトラヒドロ
−２−ナフチル）Ｎ−（６−メトキシ−２−ピリジル）
−Ｎ−メチルチオカーバメイトの含水率は２０〜７０％
（重量％）、更に好ましくは、３８〜５０％程度であ
る。含水率が７０％を越えた場合は含水粗製該チオカー
バメイトを再結晶溶媒に熱時溶解することが困難にな
り、多量の再結晶溶媒が必要になる。又、含水率２０％
未満では純度が９９．９％未満になり、目的の高純度チ
オカーバメイトを得ることは困難である。Crude O- (5,6,7,8-tetrahydro-2-naphthyl) N- (6-methoxy-2-pyridyl)
-N-methylthiocarbamate has a water content of 20 to 70%
(Wt%), more preferably about 38 to 50%. If the water content exceeds 70%, it becomes difficult to dissolve the water-containing crude thiocarbamate in the recrystallization solvent under heat, and a large amount of recrystallization solvent is required. Also, the water content is 20%
If it is less than 9, the purity will be less than 99.9%, and it is difficult to obtain the desired high-purity thiocarbamate.
【００１０】再結晶に用いるＣ1 〜Ｃ3 のアルコールと
してはメタノール、エタノール、ｎ−プロピルアルコー
ル、イソプロピルアルコールが挙げられる。アルコール
の量は含水粗製Ｏ−（５，６，７，８−テトラヒドロ−
２−ナフチル）Ｎ−（６−メトキシ−２−ピリジル）−
Ｎ−メチルチオカーバメイトの２．３倍量から９倍量、
好ましくは３．５倍量から４．５倍量程度である。The C 1 -C 3 alcohol used for recrystallization includes methanol, ethanol, n-propyl alcohol and isopropyl alcohol. The amount of alcohol is water-containing crude O- (5,6,7,8-tetrahydro-
2-naphthyl) N- (6-methoxy-2-pyridyl)-
2.3 to 9 times the amount of N-methylthiocarbamate,
The amount is preferably about 3.5 times to about 4.5 times.
【００１１】又、再結晶に用いる活性炭の量は、粗製Ｏ
−（５，６，７，８−テトラヒドロ−２−ナフチル）Ｎ
−（６−メトキシ−２−ピリジル）−Ｎ−メチルチオカ
ーバメイトに対して０．５〜５％（重量％）程度であ
る。Further, the amount of activated carbon used for recrystallization is the crude O
-(5,6,7,8-tetrahydro-2-naphthyl) N
It is about 0.5 to 5% (% by weight) with respect to-(6-methoxy-2-pyridyl) -N-methylthiocarbamate.
【００１２】本発明方法に使用する脱ハロゲン化水素剤
としては、アルカリ金属水酸化物、アルカリ土類金属水
酸化物、そして、アルカリ金属炭酸塩等の無機塩が挙げ
られるが、通常は、炭酸ナトリウム、炭酸カリウム等の
アルカリ金属炭酸塩を反応溶媒中に分散させて用いるこ
とができる。Examples of the dehydrohalogenating agent used in the method of the present invention include alkali metal hydroxides, alkaline earth metal hydroxides, and inorganic salts such as alkali metal carbonates. An alkali metal carbonate such as sodium or potassium carbonate can be used by dispersing it in a reaction solvent.
【００１３】この時、反応に用いる溶媒組成は、イソプ
ロピルアルコールと水のと重量混合比が、１００：０か
ら５０：５０の組成で使用できるが、好ましくは、９
５：５から６５：３５の組成が適当である。更に、溶媒
量は、Ｏ−（５，６，７，８−テトラヒドロ−２−ナフ
チル）−クロロチオホルメイト量の３倍から２０倍、好
ましくは、４倍から１０倍量である。At this time, the solvent composition used in the reaction may be such that the mixing ratio by weight of isopropyl alcohol and water is 100: 0 to 50:50, but preferably 9
A composition of 5: 5 to 65:35 is suitable. Further, the amount of the solvent is 3 to 20 times, preferably 4 to 10 times the amount of O- (5,6,7,8-tetrahydro-2-naphthyl) -chlorothioformate.
【００１４】また、洗浄に用いるＣ1 〜Ｃ3 のアルコー
ルとしてはメタノール、エタノール、ｎ−プロピルアル
コール、イソプロピルアルコールが挙げられるが、アル
コールの量は、Ｏ−（５，６，７，８−テトラヒドロ−
２−ナフチル）−クロロチオホルメイト量の２〜１０倍
量、好ましくは、３〜５倍量が適当である。Examples of the C 1 -C 3 alcohol used for washing include methanol, ethanol, n-propyl alcohol and isopropyl alcohol. The amount of alcohol is O- (5,6,7,8-tetrahydro). −
An amount of 2 to 10 times, preferably 3 to 5 times the amount of 2-naphthyl) -chlorothioformate is suitable.
【００１５】一方、洗浄に用いる水の量は、Ｏ−（５，
６，７，８−テトラヒドロ−２−ナフチル）−クロロチ
オホルメイト量の５倍から２０倍量、好ましくは１０〜
１５倍量が適当で、２回に分け、繰り返し洗浄を行った
ほうが効果的である。On the other hand, the amount of water used for cleaning is O- (5,
5 to 20 times the amount of 6,7,8-tetrahydro-2-naphthyl) -chlorothioformate, preferably 10 to
A 15-fold amount is suitable, and it is more effective to carry out repeated washing in two times.
【００１６】[0016]
【実施例】以下、本発明を実施例により具体的に説明す
るが、本発明はこれら実施例のみに限定されるものでは
ない。EXAMPLES The present invention will be specifically described below with reference to examples, but the present invention is not limited to these examples.
【００１７】実施例１ ２−メトキシ−６−メチルアミノピリジン１４．０ｇ
（０．１０ｍｏｌ）をイソプロピルアルコール７１ｇと
水３１ｇからなる混合溶媒に溶かして、炭酸ナトリウム
１０．６ｇ（０．１０ｍｏｌ）を懸濁させて、室温にて
攪拌しながら、Ｏ−（５，６，７，８−テトラヒドロ−
２−ナフチル）−クロロチオホルメイト２２．０ｇ
（０．１０ｍｏｌ）を約一時間かけて滴下した。滴下終
了後、更に十二時間、攪拌を継続した。反応終了後、ス
ラリー状の反応混合物をろ過し、更に遠心ろ過しながら
イソプロピルアルコール１０３．８ｇをかけて洗浄し、
次に固体を取り出し水１４０．０ｇに分散後、遠心ろ過
することにより水洗したが、この水洗の操作は二回繰り
返し、含水粗製Ｏ−（５，６，７，８−テトラヒドロ−
２−ナフチル）Ｎ−（６−メトキシ−２−ピリジル）−
Ｎ−メチルチオカーバメイト４６．８５ｇを得た。Example 1 14.0 g of 2-methoxy-6-methylaminopyridine
(0.10 mol) was dissolved in a mixed solvent consisting of 71 g of isopropyl alcohol and 31 g of water to suspend 10.6 g (0.10 mol) of sodium carbonate, and the mixture was stirred at room temperature while O- (5,6,6). 7,8-Tetrahydro-
2-naphthyl) -chlorothioformate 22.0 g
(0.10 mol) was added dropwise over about 1 hour. After completion of dropping, stirring was continued for 12 hours. After the completion of the reaction, the reaction mixture in the form of a slurry is filtered and further washed with 103.8 g of isopropyl alcohol while being centrifugally filtered.
Next, the solid was taken out, dispersed in 140.0 g of water, and washed with water by centrifugal filtration. This washing operation was repeated twice, and the water-containing crude O- (5,6,7,8-tetrahydro-
2-naphthyl) N- (6-methoxy-2-pyridyl)-
46.85 g of N-methylthiocarbamate was obtained.
【００１８】得られた含水粗製チオカーバメイトをガス
クロマトグラフィー（検出器：ＦＩＤ、Ｓｈｉｍａｄｚ
ｕ ＧＣ−７Ａ、カラム：Ｓｉｌｉｃｏｎ ＯＶ−１０
１Ｃｈｒｏｍｏｓｏｒｂ ＷＡＷ ＤＭＣＳ ３．２ｍ
ｍｘ１．６ｍ、キャリアガス：Ｎ2 １ｋｇ／ｃｍ2 ）
で分析したところ含水率は３８．２％であり、含有され
る該チオカーバメイトの重量は２８．９５ｇ（クロロチ
オホルメイトからの収率９０．９％）であった。The obtained water-containing crude thiocarbamate was subjected to gas chromatography (detector: FID, Shimadz).
u GC-7A, column: Silicon OV-10
1Chromsorb WAW DMCS 3.2m
mx 1.6 m, carrier gas: N 2 1 kg / cm 2 )
The water content was 38.2%, and the weight of the thiocarbamate contained was 28.95 g (yield from chlorothioformate 90.9%).
【００１９】この含水粗製チオカーバメイトを１０．０
ｇ取り、４３．４ｇ（含有チオカーバメイトの重量に対
して７倍量）のイソプロピルアルコールに６５〜７０℃
で加熱溶解して、活性炭０．３１ｇ（該チオカーバメイ
トに対し５ｗ／ｗ％）を加えて更に加熱後、活性炭をろ
別した。ろ液を放冷後、析出した淡黄色結晶をろ取し、
乾燥して、精製Ｏ−（５，６，７，８−テトラヒドロ−
２−ナフチル）Ｎ−（６−メトキシ−２−ピリジル）−
Ｎ−メチルチオカーバメイト４．８６ｇ（クロロチオホ
ルメイトからの収率７１．３％）を得た。This water-containing crude thiocarbamate was added to 10.0
g to 43.4 g (7 times the amount of thiocarbamate contained) in isopropyl alcohol at 65-70 ° C
Was dissolved by heating in, and 0.31 g of activated carbon (5 w / w% with respect to the thiocarbamate) was added and further heated, and then the activated carbon was filtered off. After allowing the filtrate to cool, the precipitated pale yellow crystals were collected by filtration,
Dried and purified O- (5,6,7,8-tetrahydro-
2-naphthyl) N- (6-methoxy-2-pyridyl)-
4.86 g of N-methylthiocarbamate (71.3% yield from chlorothioformate) was obtained.
【００２０】得られた精製チオカーバメイトについて液
体クロマトグラフィー（検出器：ＵＶ−８０００、カラ
ム順相ＴＳＫｇｅｌ Ｓｉ−６０、４．６ｍｍ×２５ｃ
ｍ、溶離液：ｎ−ヘキサン／酢酸エチル／アセトニトリ
ル＝９８／２／０．３）により分析したところ、純度は
９９．９３％であった。また、一方、再結晶前の粗製チ
オカーバメイトの純度は、９９．３１％であった。The purified thiocarbamate thus obtained was subjected to liquid chromatography (detector: UV-8000, column normal phase TSKgel Si-60, 4.6 mm × 25c).
m, eluent: n-hexane / ethyl acetate / acetonitrile = 98/2 / 0.3), the purity was 99.93%. On the other hand, the purity of the crude thiocarbamate before recrystallization was 99.31%.
【００２１】実施例２ 実施例１で得られた含水粗製Ｏ−（５，６，７，８−テ
トラヒドロ−２−ナフチル）Ｎ−（６−メトキシ−２−
ピリジル）−Ｎ−メチルチオカーバメイトをやはり１
０．０ｇ取り、５０℃で三時間乾燥した後、水を加えて
２０％含水粗製Ｏ−（５，６，７，８−テトラヒドロ−
２−ナフチル）Ｎ−（６−メトキシ−２−ピリジル）−
Ｎ−メチルチオカーバメイトを調製した。この含水粗製
該チオカーバメイトを実施例１と同様にイソプロピルア
ルコール４３．４ｇと活性炭０．３１ｇを用いて再結晶
したところ精製チオカーバメイトが４．８１ｇ（クロロ
チオホルメイトからの収率７０．５２％）得られた。得
られたチオカーバメイトの分析結果を表１に示した。Example 2 Water-containing crude O- (5,6,7,8-tetrahydro-2-naphthyl) N- (6-methoxy-2-) obtained in Example 1
Pyridyl) -N-methylthiocarbamate is also 1
After taking 0.0 g and drying at 50 ° C. for 3 hours, water was added to give 20% water-containing crude O- (5,6,7,8-tetrahydro-
2-naphthyl) N- (6-methoxy-2-pyridyl)-
N-methylthiocarbamate was prepared. This water-containing crude thiocarbamate was recrystallized in the same manner as in Example 1 using 43.4 g of isopropyl alcohol and 0.31 g of activated carbon to obtain 4.81 g of purified thiocarbamate (yield of 70.52% from chlorothioformate). ) Got it. Table 1 shows the analysis results of the obtained thiocarbamate.
【００２２】実施例３、４ 実施例１で得られた含水粗製チオカーバメイトを８．０
６ｇずつ取り、更に水を加えて含水率５０％で１０．０
ｇ及び含水率６７％で１５．１５ｇの含水粗製チオカー
バメイトを調製した。これらの含水チオカーバメイトを
実施例１と同様にイソプロピルアルコール３５．０ｇ
（含有チオカーバメイト重量に対して７倍量）から活性
炭０．２５ｇ（含有該チオカーバメイトに対して５ｗ／
ｗ％）を用いて再結晶を行ったところ、精製チオカーバ
メイトをそれぞれ４．２０ｇ（クロロチオホルメイトか
らの収率７６．３４％）及び４．２６ｇ（クロロチオホ
ルメイトからの収率７７．４５％）を得た。これらのチ
オカーバメイトの分析結果を表１に示した。Examples 3 and 4 The hydrous crude thiocarbamate obtained in Example 1 was 8.0.
Take 6g each and add more water to obtain a water content of 50% 10.0
g and 15.15 g of water-containing crude thiocarbamate with a water content of 67% was prepared. These hydrous thiocarbamates were treated with 35.0 g of isopropyl alcohol in the same manner as in Example 1.
(7 times the amount of the contained thiocarbamate) to 0.25 g of activated carbon (5w / based on the contained thiocarbamate)
Recrystallization was performed using 4.20 g (yield 76.34% from chlorothioformate) and 4.26 g (yield 77.34% from chlorothioformate) of purified thiocarbamate, respectively. 45%). The results of analysis of these thiocarbamates are shown in Table 1.
【００２３】比較例 実施例１で得られた含水粗製チオカーバメイト１０．０
ｇを減圧乾燥（５０℃、３時間）し、やはりイソプロピ
ルアルコール４３．４ｇから活性炭０．３１ｇを用いて
再結晶を行ったところ精製チオカーバメイト４．８５ｇ
（クロロチオホルメイトからの収率７１．１％）を得
た。得られたチオカーバメイトの分析結果を表１に示し
た。Comparative Example Hydrous crude thiocarbamate 10.0 obtained in Example 1
g was dried under reduced pressure (50 ° C., 3 hours) and again recrystallized from 43.4 g of isopropyl alcohol using 0.31 g of activated carbon to obtain 4.85 g of purified thiocarbamate.
(71.1% yield from chlorothioformate) was obtained. Table 1 shows the analysis results of the obtained thiocarbamate.
【００２４】[0024]
【表１】 [Table 1]
【００２５】[0025]
【発明の効果】以上の説明で明らかなように、本発明製
造法に従えば、高純度のＯ−（５，６，７，８−テトラ
ヒドロ−２−ナフチル）Ｎ−（６−メトキシ−２−ピリ
ジル）−Ｎ−メチルチオカーバメイトを、純度９９．９
％５以上で得ることができる。As is apparent from the above description, according to the production method of the present invention, highly pure O- (5,6,7,8-tetrahydro-2-naphthyl) N- (6-methoxy-2) is obtained. -Pyridyl) -N-methylthiocarbamate with a purity of 99.9.
It can be obtained at% 5 or more.
Claims (1)
−ナフチル）−クロロチオホルメイトと２−メトキシ−
６−メチルアミノピリジンを脱ハロゲン化水素剤存在
下、含水イソプロピルアルコール溶媒中で縮合して得ら
れた粗製Ｏ−（５，６，７，８−テトラヒドロ−２−ナ
フチル）Ｎ−（６−メトキシ−２−ピリジル）−Ｎ−メ
チルチオカ−バメイトを、含水率２０〜７０％に調製
し、活性炭を加えてＣ1 〜Ｃ3 のアルコールから再結晶
することを特徴とする高純度Ｏ−（５，６，７，８−テ
トラヒドロ−２−ナフチル）Ｎ−（６−メトキシ−２−
ピリジル）−Ｎ−メチルチオカーバメイトの製造方法。Claims: 1. O- (5,6,7,8-tetrahydro-2
-Naphthyl) -chlorothioformate and 2-methoxy-
Crude O- (5,6,7,8-tetrahydro-2-naphthyl) N- (6-methoxy) obtained by condensing 6-methylaminopyridine in a hydrous isopropyl alcohol solvent in the presence of a dehydrohalogenating agent. 2-Pyridyl) -N-methylthiocarbamate was prepared to a water content of 20 to 70%, activated carbon was added, and recrystallized from a C 1 to C 3 alcohol to obtain high purity O- (5, 6,7,8-Tetrahydro-2-naphthyl) N- (6-methoxy-2-
Process for producing pyridyl) -N-methylthiocarbamate.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3210472A JP3030732B2 (en) | 1991-07-29 | 1991-07-29 | Method for producing high-purity methylthiocarbamate |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3210472A JP3030732B2 (en) | 1991-07-29 | 1991-07-29 | Method for producing high-purity methylthiocarbamate |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH0532629A true JPH0532629A (en) | 1993-02-09 |
| JP3030732B2 JP3030732B2 (en) | 2000-04-10 |
Family
ID=16589909
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP3210472A Expired - Fee Related JP3030732B2 (en) | 1991-07-29 | 1991-07-29 | Method for producing high-purity methylthiocarbamate |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP3030732B2 (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2005350447A (en) * | 2004-05-12 | 2005-12-22 | Tosoh Corp | O-(5,6,7,8-tetrahydro-2-naphthyl)-n-(6-methoxy-2-pyridyl)-n-methylthiocarbamate and method for producing the same |
| JP2006298832A (en) * | 2005-04-21 | 2006-11-02 | Tosoh Corp | High-purity o-(5,6,7,8-tetrahydro-2-naphthyl)-n-(6-methoxy-2-pyridyl)-n-methylthiocarbamate and its preparation method |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR101362299B1 (en) * | 2004-05-12 | 2014-02-12 | 토소가부시키가이샤 | O-(5, 6, 7, 8-tetrahydro-2-naphthyl)-n-(6-methoxy-2-pyridyl)-n-methyl thiocarbomate and producing process |
| KR102119750B1 (en) | 2018-11-26 | 2020-06-08 | 가톨릭대학교 산학협력단 | Clothing for breast examination |
-
1991
- 1991-07-29 JP JP3210472A patent/JP3030732B2/en not_active Expired - Fee Related
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2005350447A (en) * | 2004-05-12 | 2005-12-22 | Tosoh Corp | O-(5,6,7,8-tetrahydro-2-naphthyl)-n-(6-methoxy-2-pyridyl)-n-methylthiocarbamate and method for producing the same |
| JP2006298832A (en) * | 2005-04-21 | 2006-11-02 | Tosoh Corp | High-purity o-(5,6,7,8-tetrahydro-2-naphthyl)-n-(6-methoxy-2-pyridyl)-n-methylthiocarbamate and its preparation method |
Also Published As
| Publication number | Publication date |
|---|---|
| JP3030732B2 (en) | 2000-04-10 |
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