JPH0449542B2 - - Google Patents
Info
- Publication number
- JPH0449542B2 JPH0449542B2 JP7440385A JP7440385A JPH0449542B2 JP H0449542 B2 JPH0449542 B2 JP H0449542B2 JP 7440385 A JP7440385 A JP 7440385A JP 7440385 A JP7440385 A JP 7440385A JP H0449542 B2 JPH0449542 B2 JP H0449542B2
- Authority
- JP
- Japan
- Prior art keywords
- pyridylamines
- sulfite
- aromatic amines
- reaction
- pyridylthiocarbamoyl
- 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
- 150000004982 aromatic amines Chemical class 0.000 claims description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- RYFZYYUIAZYQLC-UHFFFAOYSA-N perchloromethyl mercaptan Chemical compound ClSC(Cl)(Cl)Cl RYFZYYUIAZYQLC-UHFFFAOYSA-N 0.000 claims description 7
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 6
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 claims description 5
- 239000003153 chemical reaction reagent Substances 0.000 claims description 5
- 238000006704 dehydrohalogenation reaction Methods 0.000 claims description 5
- 239000003960 organic solvent Substances 0.000 claims description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 description 12
- 238000004458 analytical method Methods 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 150000001805 chlorine compounds Chemical class 0.000 description 6
- -1 Alkali metal hydrogen sulfites Chemical class 0.000 description 5
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 238000000921 elemental analysis Methods 0.000 description 4
- 230000000704 physical effect Effects 0.000 description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
- GXHQLRBOZRJHPZ-UHFFFAOYSA-N 6-methoxy-n-methylpyridin-2-amine Chemical compound CNC1=CC=CC(OC)=N1 GXHQLRBOZRJHPZ-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- ZWZVWGITAAIFPS-UHFFFAOYSA-N thiophosgene Chemical compound ClC(Cl)=S ZWZVWGITAAIFPS-UHFFFAOYSA-N 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-aminopyridine Chemical compound NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- OJGMBLNIHDZDGS-UHFFFAOYSA-N N-Ethylaniline Chemical compound CCNC1=CC=CC=C1 OJGMBLNIHDZDGS-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 2
- 238000000862 absorption spectrum Methods 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- OYPDOAZYDUMORG-UHFFFAOYSA-N n-methylcarbamothioyl chloride Chemical compound CNC(Cl)=S OYPDOAZYDUMORG-UHFFFAOYSA-N 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 2
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 2
- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 1
- PQUCIEFHOVEZAU-UHFFFAOYSA-N Diammonium sulfite Chemical compound [NH4+].[NH4+].[O-]S([O-])=O PQUCIEFHOVEZAU-UHFFFAOYSA-N 0.000 description 1
- AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methylaniline Chemical compound CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 230000002159 abnormal effect Effects 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- 229910001516 alkali metal iodide Inorganic materials 0.000 description 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
- 150000003927 aminopyridines Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- ZETCGWYACBNPIH-UHFFFAOYSA-N azane;sulfurous acid Chemical compound N.OS(O)=O ZETCGWYACBNPIH-UHFFFAOYSA-N 0.000 description 1
- NBYQXBYMEUOBON-UHFFFAOYSA-N carbamothioyl chloride Chemical class NC(Cl)=S NBYQXBYMEUOBON-UHFFFAOYSA-N 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- ONJLWIHTFJQMQI-UHFFFAOYSA-N n-(6-methoxypyridin-2-yl)-n-methylcarbamothioyl chloride Chemical compound COC1=CC=CC(N(C)C(Cl)=S)=N1 ONJLWIHTFJQMQI-UHFFFAOYSA-N 0.000 description 1
- VSVGLMSXVIDZDG-UHFFFAOYSA-N n-methyl-n-phenylcarbamothioyl chloride Chemical compound ClC(=S)N(C)C1=CC=CC=C1 VSVGLMSXVIDZDG-UHFFFAOYSA-N 0.000 description 1
- SVEUVITYHIHZQE-UHFFFAOYSA-N n-methylpyridin-2-amine Chemical compound CNC1=CC=CC=N1 SVEUVITYHIHZQE-UHFFFAOYSA-N 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- BHAAPTBBJKJZER-UHFFFAOYSA-N p-anisidine Chemical compound COC1=CC=C(N)C=C1 BHAAPTBBJKJZER-UHFFFAOYSA-N 0.000 description 1
- DJEHXEMURTVAOE-UHFFFAOYSA-M potassium bisulfite Chemical compound [K+].OS([O-])=O DJEHXEMURTVAOE-UHFFFAOYSA-M 0.000 description 1
- 235000010259 potassium hydrogen sulphite Nutrition 0.000 description 1
- BHZRJJOHZFYXTO-UHFFFAOYSA-L potassium sulfite Chemical compound [K+].[K+].[O-]S([O-])=O BHZRJJOHZFYXTO-UHFFFAOYSA-L 0.000 description 1
- 235000019252 potassium sulphite Nutrition 0.000 description 1
- 150000003142 primary aromatic amines Chemical class 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 229940079827 sodium hydrogen sulfite Drugs 0.000 description 1
- 235000010265 sodium sulphite Nutrition 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical class [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
- 150000004992 toluidines Chemical class 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Landscapes
- Pyridine Compounds (AREA)
- 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〕
本発明はチオカルバモイル クロライド類の製
造法に関する。さらに詳しくはフエニル又はピリ
ジルチオカルバモイル クロライドに関する。
フエニル又はピリジルチオカルバモイル クロ
ライド類は医薬，農薬の中間体として非常に有用
である。
〔従来の技術〕
フエニル又はピリジルチオカルバモイル クロ
ライド類は、脱ハロゲン化水素試剤存在下で芳香
族アミンン類又はピリジルアミン類とチオホスゲ
ンの反応により製造できることは公知である。
〔発明が解決するための問題点〕
チオホスゲンは毒性が高いため、取り扱いは非
常に注意を要する。漏洩等の異常事態を考慮する
と大量の貯蔵又は移動は出来るだけ回避すること
が望ましい。
本発明の目的は大量のチオホスゲンの貯蔵又は
移動を回避し簡便にしかも、安全にフエニル又は
ピリジルチオカルバモイル クロライド類を製造
することにある。
〔発明が解決するための手段，作用〕
本発明者らは種々の試験をし鋭意検討した結
果、パークロルメチルメルカプタン，亜硫酸化
物，濃硫酸を有機溶媒存在下に反応させた後、芳
香族アミン類又はピリジルアミン類と脱ハロゲン
化水素試剤を添加することによりフエニル又はピ
リジルチオカルバモイル クロライド類を製造出
来ることを見い出し本発明を完成した。
次に本発明の実施方法について詳しく述べる。
パークロルメチルメルカプタン，亜硫酸化物，
濃硫酸を有機溶媒存在下に反応させる。
亜硫酸化物としては、亜硫酸水素ナトリウム，
亜硫酸水素カリウム等のアルカリ金属亜硫酸水素
化物、亜硫酸ナトリウム，亜硫酸カリウム等のア
ルカリ金属亜硫酸化物、亜硫酸水素アンモニウ
ム、亜硫酸アンモニウム等を用いることができ
る。
有機溶媒としては、クロロホルム，ジクロルメ
タン，四塩化炭素等の塩素化炭化水素、ベンゼ
ン，トルエン，キシレン等の芳香族炭化水素等が
挙げられる。パークロルメチルメルカプタン，亜
硫酸化物は芳香族アミン類又はピリジルアミン類
に対して等モル以上用いる。そして濃硫酸はパー
クロルメチルメルカプタンの約1/10倍モル以上用
いる。
さらに、反応を円滑に進めるために少量のアル
カリ金属ヨウ化物及びパークロルメチルメルカプ
タタンに対して約１倍モル以上の水を添加でき
る。
反応終了後、芳香族アミン類又はピリジルアミ
ン類と脱ハロゲン化水素試剤を添加する。
芳香族アミン類としては、例えばアニリン，ト
ルイジン，アニシジン等の一級芳香族アミン，Ｎ
−メチルアニリン，Ｎ−エチルアニリン等の二級
芳香族アミン等、またピリジルアミン類としては
例えば２−アミノピリジン，６−メトキシ−２−
アミノピリジン等の一級ピリジルアミン，２−メ
チルアミノピリジン，２−メトキシ−６−メチル
アミノピリジン等の２級ピリジルアミン等を用い
ることができる。
脱ハロゲン化水素試剤としては、アルカリ金属
水酸化物，アルカリ土類金属水酸化物，アルカリ
金属炭酸塩等の無機塩基、トリエチルアミン，ピ
リジン，キノリン，イソキノリン等の有機塩基等
が挙げられるが、通常は、水酸化ナトリウム，水
酸化カリウム等のアルカリ金属水酸化物を水に溶
解して使用する。脱ハロゲン化水素試剤は添加前
に反応液より水層を除去すれば、芳香族アミン類
又はピリジルアミン類と約当量でよい。
反応温度は、通常約−10℃〜室温が選ばれ、反
応は24時間以内に完結させることができる。
〔発明の効果〕
パークロルメチルメルカプタン，亜硫酸化物及
び濃硫酸を有機溶媒存在下に反応させた後、芳香
族アミン類又はピリジルアミン類と脱ハロゲン化
水素試剤を添加することにより、簡便にしかも安
全にフエニル又はピリジルチオカルバモイル ク
ロライド類を製造できる。
次に実施例でもつて本発明を詳細に説明するが
本発明はこれら実施例のみに限定されるものでは
ない。
〔実施例〕
実施例 １
撹拌機、温度計，300mlの滴下漏斗を付した１
の３つ口フラスコにパークロルメチルメルカプ
タン135ｇ，亜硫酸水素ナトリウム250ｇ，四塩化
炭素200ml，水170ml、そしてヨウ化カリウム２ｇ
を取りフラスコを氷冷した。
次いで、上記溶液に濃硫酸40mlを添加し、10時
間撹拌した。フラスコ内の温度は、滴下時は０℃
以後は室温に保つた。
反応液より水層を除去し、残つた有機層に２−
メトキシ−６−メチルアミノピリジン100ｇと10
％水酸化ナトリウム水溶液300mlを滴下し、さら
に２時間撹拌した。
反応終了後、反応液より有機層を分取し、蒸留
によりＮ−（６−メトキシ−２−ピリジル）−Ｎ−
メチル−チオカルバモイル クロライド47ｇを得
た。Ｎ−（６−メトキシ−２−ピリジル）−Ｎ−メ
チルチオカルバモイル クロライドの収率は２−
メトキシ−６−メチルアミノピリジン基準で30％
であつた。
得られたＮ−（６−メトキシ−２−ピリジル）−
Ｎ−メチル−チオカルバモイル クロライドの物
性値は次のとおりであつた。
元素分析（％）
Ｃ Ｈ Ｎ Cl
分析値 44.37 4.06 12.73 16.22
計算値 44.34 4.18 12.92 16.36
Ｓ
分折値 15.03
計算値 14.80
赤外吸収スペクトル（NaCl：cm-1）
3000，2950，1610，1596，1570，1476，1420
実施例 ２〜４
実施例１と同一の反応装置に、表−１に示した
芳香族アミン類又はピリジルアミン類を取り表−
１の反応条件下で反応を行い実施例１と同様の処
理をし、フエニル又はピリジルチオカルバモイル
クロライド類を得た。
その結果を表−１に示す。
得られたＮ−４−（メチルフエニル）−チオカル
バモイル クロライドの物性値は次のとおりであ
つた。
元素分析（％）
Ｃ Ｈ Ｎ Cl
分析値 51.92 4.30 7.27 19.01
計算値 51.75 4.34 7.54 19.09
Ｓ
分折値 17.50
計算値 17.28
得られたＮ−メチル−Ｎ−フエニルチオカルバ
モイル クロライドの物性値は次のとおりであつ
た。
元素分析（％）
Ｃ Ｈ Ｎ Cl
分析値 51.57 4.37 7.62 18.93
計算値 51.75 4.34 7.54 19.09
Ｓ
分折値 17.51
計算値 17.28
赤外吸収スペクトル（NaCl：cm-1）
3020，2980，1600，1496，1380
得られたＮ−（２−ピリジル）−チオカルバモイ
ル クロライドの物性値は次のとおりであつた。
元素分析（％）
Ｃ Ｈ Ｎ Cl
分析値 41.62 3.09 16.51 19.62
計算値 41.75 2.91 16.23 20.54
Ｓ
分折値 19.16
計算値 18.57
【表】DETAILED DESCRIPTION OF THE INVENTION [Industrial Field of Application] The present invention relates to a method for producing thiocarbamoyl chlorides. More specifically, it relates to phenyl or pyridylthiocarbamoyl chloride. Phenyl or pyridylthiocarbamoyl chlorides are very useful as intermediates for pharmaceuticals and agricultural chemicals. [Prior Art] It is known that phenyl or pyridylthiocarbamoyl chlorides can be produced by reacting aromatic amines or pyridylamines with thiophosgene in the presence of a dehydrohalogenating agent. [Problems to be solved by the invention] Since thiophosgene is highly toxic, it must be handled with great care. Considering abnormal situations such as leakage, it is desirable to avoid storing or moving large quantities as much as possible. An object of the present invention is to avoid the storage or transfer of large amounts of thiophosgene and to easily and safely produce phenyl or pyridylthiocarbamoyl chlorides. [Means and effects for solving the invention] As a result of various tests and intensive studies, the present inventors found that after reacting perchloromethyl mercaptan, sulfite, and concentrated sulfuric acid in the presence of an organic solvent, aromatic amines The present invention was completed based on the discovery that phenyl or pyridylthiocarbamoyl chlorides can be produced by adding pyridylamines or pyridylamines and a dehydrohalogenating agent. Next, a method of implementing the present invention will be described in detail. Perchloromethyl mercaptan, sulfite,
Concentrated sulfuric acid is reacted in the presence of an organic solvent. Sulfites include sodium hydrogen sulfite,
Alkali metal hydrogen sulfites such as potassium hydrogen sulfite, alkali metal sulfites such as sodium sulfite and potassium sulfite, ammonium hydrogen sulfite, ammonium sulfite, etc. can be used. Examples of the organic solvent include chlorinated hydrocarbons such as chloroform, dichloromethane, and carbon tetrachloride, and aromatic hydrocarbons such as benzene, toluene, and xylene. Perchlormethyl mercaptan and sulfite are used in an amount equal to or more than the same mole relative to aromatic amines or pyridylamines. Concentrated sulfuric acid is used at a mole greater than about 1/10 times that of perchloromethyl mercaptan. Furthermore, in order to proceed with the reaction smoothly, water can be added in an amount of about 1 mole or more relative to a small amount of alkali metal iodide and perchloromethyl mercaptatan. After the reaction is completed, aromatic amines or pyridylamines and a dehydrohalogenation reagent are added. Examples of aromatic amines include primary aromatic amines such as aniline, toluidine, and anisidine, N
- Secondary aromatic amines such as methylaniline, N-ethylaniline, etc., and pyridylamines such as 2-aminopyridine, 6-methoxy-2-
Primary pyridylamines such as aminopyridine, secondary pyridylamines such as 2-methylaminopyridine, 2-methoxy-6-methylaminopyridine, etc. can be used. Examples of dehydrohalogenation reagents include inorganic bases such as alkali metal hydroxides, alkaline earth metal hydroxides, and alkali metal carbonates, and organic bases such as triethylamine, pyridine, quinoline, and isoquinoline. , sodium hydroxide, potassium hydroxide, and other alkali metal hydroxides are used by dissolving them in water. The dehydrohalogenation reagent may be used in an amount approximately equivalent to that of the aromatic amines or pyridylamines, provided that the aqueous layer is removed from the reaction solution before addition. The reaction temperature is usually about -10°C to room temperature, and the reaction can be completed within 24 hours. [Effect of the invention] After reacting perchloromethyl mercaptan, sulfite and concentrated sulfuric acid in the presence of an organic solvent, aromatic amines or pyridyl amines and a dehydrohalogenation reagent are added to the reaction, which is simple and safe. phenyl or pyridylthiocarbamoyl chlorides can be produced. Next, the present invention will be explained in detail with reference to Examples, but the present invention is not limited to these Examples. [Example] Example 1 1 with a stirrer, thermometer, and 300 ml dropping funnel
In a three-necked flask, add 135 g of perchloromethyl mercaptan, 250 g of sodium bisulfite, 200 ml of carbon tetrachloride, 170 ml of water, and 2 g of potassium iodide.
and cooled the flask on ice. Next, 40 ml of concentrated sulfuric acid was added to the above solution and stirred for 10 hours. The temperature inside the flask is 0°C during dropping.
Thereafter, it was kept at room temperature. The aqueous layer was removed from the reaction solution, and 2-
Methoxy-6-methylaminopyridine 100g and 10
% aqueous sodium hydroxide solution was added dropwise, and the mixture was further stirred for 2 hours. After the reaction is completed, the organic layer is separated from the reaction solution and distilled to give N-(6-methoxy-2-pyridyl)-N-
47 g of methyl-thiocarbamoyl chloride was obtained. The yield of N-(6-methoxy-2-pyridyl)-N-methylthiocarbamoyl chloride is 2-
30% based on methoxy-6-methylaminopyridine
It was hot. The obtained N-(6-methoxy-2-pyridyl)-
The physical properties of N-methyl-thiocarbamoyl chloride were as follows. Elemental analysis (%) C H N Cl Analysis value 44.37 4.06 12.73 16.22 Calculated value 44.34 4.18 12.92 16.36 S Fractional value 15.03 Calculated value 14.80 Infrared absorption spectrum (NaCl: cm -1 ) 3000, 2950, 1610, 1596, 157 0, 1476, 1420 Examples 2 to 4 The aromatic amines or pyridylamines shown in Table 1 were placed in the same reaction apparatus as in Example 1.
The reaction was carried out under the reaction conditions of Example 1 and treated in the same manner as in Example 1 to obtain phenyl or pyridylthiocarbamoyl chlorides. The results are shown in Table-1. The physical properties of the obtained N-4-(methylphenyl)-thiocarbamoyl chloride were as follows. Elemental analysis (%) C H N Cl Analysis value 51.92 4.30 7.27 19.01 Calculated value 51.75 4.34 7.54 19.09 S Analysis value 17.50 Calculated value 17.28 The physical properties of the obtained N-methyl-N-phenylthiocarbamoyl chloride are as follows. It was hot. Elemental analysis (%) C H N Cl Analysis value 51.57 4.37 7.62 18.93 Calculated value 51.75 4.34 7.54 19.09 S Analysis value 17.51 Calculated value 17.28 Infrared absorption spectrum (NaCl: cm -1 ) 3020, 2980, 1600, 1496, 1380 profit The physical properties of the obtained N-(2-pyridyl)-thiocarbamoyl chloride were as follows. Elemental analysis (%) C H N Cl Analysis value 41.62 3.09 16.51 19.62 Calculated value 41.75 2.91 16.23 20.54 S Analysis value 19.16 Calculated value 18.57 [Table]
Claims (1)
物，濃硫酸を有機溶媒存在下に反応させた後、芳
香族アミン類又はピリジルアミン類と脱ハロゲン
化水素試剤を添加することを特徴とするフエニル
又はピリジルチオカルバモイル クロライド類の
製造法。1 Phenyl or pyridylthiocarbamoyl chloride characterized by reacting perchloromethyl mercaptan, sulfite, and concentrated sulfuric acid in the presence of an organic solvent, and then adding aromatic amines or pyridylamines and a dehydrohalogenation reagent. manufacturing method of types.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP7440385A JPS61233663A (en) | 1985-04-10 | 1985-04-10 | Production of thiocarbamoyl chloride |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP7440385A JPS61233663A (en) | 1985-04-10 | 1985-04-10 | Production of thiocarbamoyl chloride |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS61233663A JPS61233663A (en) | 1986-10-17 |
| JPH0449542B2 true JPH0449542B2 (en) | 1992-08-11 |
Family
ID=13546187
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP7440385A Granted JPS61233663A (en) | 1985-04-10 | 1985-04-10 | Production of thiocarbamoyl chloride |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS61233663A (en) |
-
1985
- 1985-04-10 JP JP7440385A patent/JPS61233663A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS61233663A (en) | 1986-10-17 |
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