JPH1059922A - Production of o-alkyl-n-cyanoimidate - Google Patents

Production of o-alkyl-n-cyanoimidate

Info

Publication number
JPH1059922A
JPH1059922A JP8235816A JP23581696A JPH1059922A JP H1059922 A JPH1059922 A JP H1059922A JP 8235816 A JP8235816 A JP 8235816A JP 23581696 A JP23581696 A JP 23581696A JP H1059922 A JPH1059922 A JP H1059922A
Authority
JP
Japan
Prior art keywords
reaction
acid
mol
alcohol
caim
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
Application number
JP8235816A
Other languages
Japanese (ja)
Other versions
JP3306312B2 (en
Inventor
Takehiko Yoshie
江 武 彦 吉
Shusuke Niizeki
タ 秀 典 新
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Nippon Carbide Industries Co Inc
Original Assignee
Nippon Carbide Industries Co Inc
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Nippon Carbide Industries Co Inc filed Critical Nippon Carbide Industries Co Inc
Priority to JP23581696A priority Critical patent/JP3306312B2/en
Publication of JPH1059922A publication Critical patent/JPH1059922A/en
Application granted granted Critical
Publication of JP3306312B2 publication Critical patent/JP3306312B2/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

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Classifications

    • YGENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02PCLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00Technologies relating to chemical industry
    • Y02P20/50Improvements relating to the production of bulk chemicals
    • Y02P20/52Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts

Landscapes

  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

PROBLEM TO BE SOLVED: To produce the subject compound which is useful as an intermediate for medicines or agrochemicals in high yield by reaction of a nitrile compound with an alcohol without isolation of its intermediate. SOLUTION: A compound bearing a nitrile group (acetonitrile) in an amount of 1 mole and an alcohol (methanol) in an amount of 0.7-5 moles (preferably 0.9-2 moles) are dissolved in a nonpolar solvent in the presence of an acid and subjected to the reaction between them. The acid used in this reaction is an inorganic acid such as hydrochloric acid and the amount of the acid is set to 0.7-5 moles per mole of the nitrile and the reaction temperature is -10-20 deg.C. In the reaction, the alcohol is sequentially added to 1 mole of the nitrile by 0.8-2 moles, preferably 0.9-1.5 mole and the reaction mixture is heated at 20-100 deg.C to effect the reaction. After completion of the reaction, the salt formed as a by-product is separated.

Description

【発明の詳細な説明】DETAILED DESCRIPTION OF THE INVENTION

【0001】[0001]

【発明の属する技術分野】本発明は医薬及び農薬中間体
として有用なO−アルキル−N−シアノイミデートの製
造法に関するものであり、詳しくは、ニトリル基を有す
る化合物とアルコールとを塩酸の存在下非極性溶媒中で
反応させ、次いで得られる反応液にアミノニトリルを加
え加熱することを特徴とするO−アルキル−N−シアノ
イミデートの製造方法に関するものである。
TECHNICAL FIELD The present invention relates to a process for producing O-alkyl-N-cyanoimidate useful as an intermediate for pharmaceuticals and agricultural chemicals, and more particularly, to a process for producing a compound having a nitrile group and an alcohol in the presence of hydrochloric acid. The present invention relates to a method for producing O-alkyl-N-cyanoimidate, comprising reacting in a lower nonpolar solvent, then adding aminonitrile to the resulting reaction solution and heating.

【0002】[0002]

【従来の技術】O−アルキル−N−シアノイミデートの
製造法については、従来いくつかの方法が知られてお
り、例えばチェコスロバキア国特許第 273050 号にはO
−メチルアセトイミド塩酸塩をメタノール中でシアナミ
ドと反応させ,O−メチル−N−シアノアセトイミデー
ト(以下CAIMと略称することがある)を製造する方法に
ついて提案されている。
2. Description of the Related Art Several methods for producing O-alkyl-N-cyanoimidates are known in the art. For example, Czechoslovak Patent No. 273050 discloses an O-alkyl-N-cyanoimidate.
A method for producing O-methyl-N-cyanoacetimidate (hereinafter sometimes abbreviated as CAIM) by reacting -methylacetimide hydrochloride with cyanamide in methanol has been proposed.

【0003】[0003]

【化1】 Embedded image

【0004】この提案においてはO−メチルアセトイミ
ド塩酸塩とシアナミドを無水メタノール中で反応させ、
濾過により副成した塩化アンモニウム結晶を分離した
後、ろ液をO−メチル−N−シアノアセトイミデート溶
液として次工程に使用している。
In this proposal, O-methylacetimide hydrochloride and cyanamide are reacted in anhydrous methanol,
After the by-product ammonium chloride crystals were separated by filtration, the filtrate was used in the next step as an O-methyl-N-cyanoacetimidate solution.

【0005】しかしながら前記方法においては、副成す
る塩化アンモニウム結晶はメタノールに溶解してしま
い、濾液中に大量に混入して工業的な大スケールの反応
においては実施が困難であった。
[0005] However, in the above method, ammonium chloride crystals formed as by-products are dissolved in methanol and mixed in a large amount into the filtrate, making it difficult to carry out the reaction in an industrial large-scale reaction.

【0006】またO−メチル−N−シアノアセトイミデ
ートを単離する場合には、メタノール溶液から蒸留分離
しなければならず、大量の副生塩化アンモニウム存在下
の蒸留は蒸留工程の損失が多く、O−メチル−N−シア
ノアセトイミデートの単離収率は良くないものであっ
た。
When O-methyl-N-cyanoacetimidate is isolated, it must be separated by distillation from a methanol solution, and distillation in the presence of a large amount of by-product ammonium chloride causes a large loss in the distillation step. And the isolation yield of O-methyl-N-cyanoacetimidate was poor.

【0007】一方、ドイツ国特許公報 DE3815084 号に
は、オルト酢酸エステルとシアナミドをメタノール溶媒
中で反応させることにより、塩化アンモニウムの副成な
しにO−メチル−N−シアノアセトイミデートを製造す
る方法について提案されている。
On the other hand, German Patent Publication DE 3815084 discloses a process for producing O-methyl-N-cyanoacetimidate without reacting ammonium chloride by reacting orthoacetate and cyanamide in a methanol solvent. It has been proposed.

【0008】[0008]

【化2】 Embedded image

【0009】オルト酢酸エステルは特開昭52-125108
号、特開昭56-59730号等に記載されたように、O−メチ
ルアセトイミド塩のアルコーリシスによって製造される
ものであり、低沸点の引火性液体であって空気中の水分
との反応性も高く、工業的規模での取り扱いには厳重な
注意が必要とされる物質である。またO−メチルイミド
塩からオルト酢酸エステルを製造するという工程が別途
必要であって、O−メチル−N−シアノアセトイミデー
トを工業的規模で経済的に高収率で生産する方法として
は、充分なものではなかった。
Ortho acetic acid ester is disclosed in JP-A-52-125108.
As described in JP-A-56-59730, it is produced by alcoholysis of O-methylacetimide salt, is a low boiling flammable liquid, and reacts with moisture in the air. It is highly susceptible and requires strict care when handling on an industrial scale. In addition, a process of producing orthoacetic acid ester from an O-methylimide salt is separately required, which is a sufficient method for economically producing O-methyl-N-cyanoacetimidate on an industrial scale with a high yield. It was not something.

【0010】[0010]

【発明が解決しようとする課題】本発明の課題は、ニト
リル化合物とアルコールから、中間体を単離することな
しにO−アルキル−N−シアノイミデートを高収率で製
造する方法を提供することである。
An object of the present invention is to provide a method for producing O-alkyl-N-cyanoimidate in high yield from a nitrile compound and an alcohol without isolating an intermediate. That is.

【0011】[0011]

【課題を解決するための手段】本発明者等は上記課題を
解決するために、鋭意検討を重ねた結果、ニトリル基を
有する化合物とアルコールとを塩酸の存在下非極性溶媒
中で反応させ、次いで得られる反応液にシアナミドを加
え加熱することにより、中間体を単離する事なしにO−
アルキル−N−シアノイミデートを高収率で製造できる
ことを見出し、本発明を完成した。
Means for Solving the Problems The present inventors have conducted intensive studies in order to solve the above problems, and as a result, reacted a compound having a nitrile group with an alcohol in a nonpolar solvent in the presence of hydrochloric acid, Subsequently, by adding cyanamide to the obtained reaction solution and heating, O-
The present inventors have found that alkyl-N-cyanoimidate can be produced in high yield, and have completed the present invention.

【0012】以下に本発明を詳細に説明する。まずニト
リル基を有する化合物とアルコールとを非極性溶媒中で
酸接触により反応させる。ニトリル基を有する化合物と
しては 、たとえばアセトニトリル,ラクトニトリル等
の脂肪族鎖状アルキルニトリルがあげられる。
Hereinafter, the present invention will be described in detail. First, a compound having a nitrile group and an alcohol are reacted in a nonpolar solvent by acid contact. Examples of the compound having a nitrile group include aliphatic linear alkyl nitriles such as acetonitrile and lactonitrile.

【0013】[0013]

【化3】 Embedded image

【0014】アルコールとしては特に制限されないが、
メタノール、エタノール、プロパノール、ブタノール等
が好ましく、アルコールの使用量はニトリル基を有する
化合物1モルに対して 0.7〜5モル、好ましくは0.9〜2
モル、特に好ましくは1〜2モル使用する。
The alcohol is not particularly limited,
Methanol, ethanol, propanol, butanol and the like are preferred, and the amount of the alcohol used is 0.7 to 5 mol, preferably 0.9 to 2 mol, per mol of the compound having a nitrile group.
Mol, particularly preferably 1 to 2 mol.

【0015】前記ニトリル基を有する化合物とアルコー
ルとを、非極性溶媒中に溶解し、酸を逐次添加すること
により反応液を調整する。非極性溶媒としては、ニトリ
ル基を有する化合物およびアルコールと反応しない非極
性溶媒であれば特に限定されないが、ベンゼン,トルエ
ン,キシレン等の芳香族炭化水素類、ヘキサン,オクタ
ン,ドデカン等の脂肪族炭化水素類があげられるが、特
に大スケールの製造においては安全性、回収容易性、毒
性等の観点からトルエン,が特に好ましい。
The reaction solution is prepared by dissolving the compound having a nitrile group and an alcohol in a non-polar solvent and sequentially adding an acid. The non-polar solvent is not particularly limited as long as it is a non-polar solvent that does not react with a compound having a nitrile group or an alcohol, and aromatic hydrocarbons such as benzene, toluene, and xylene, and aliphatic hydrocarbons such as hexane, octane, and dodecane. Hydrogens may be mentioned, and toluene is particularly preferable from the viewpoints of safety, recoverability, toxicity and the like, particularly in large-scale production.

【0016】前記の酸としては、塩酸、臭化水素酸等の
無機酸が好ましく,取り扱い易さの点から無水塩酸ガス,
の使用が特に好ましく、酸はニトリル基を有する化合物
1モルに対して0.7〜5モル、好ましくは0.8〜2.5モル、
特に好ましくは0.9〜1.5モル使用するのが良く、前記の
酸の添加は-10℃〜20℃、好ましくは-5℃〜5℃以下で行
うのがよい。
The acid is preferably an inorganic acid such as hydrochloric acid or hydrobromic acid. From the viewpoint of easy handling, anhydrous hydrochloric acid gas,
Is particularly preferred, and the acid is used in an amount of 0.7 to 5 mol, preferably 0.8 to 2.5 mol, per 1 mol of the compound having a nitrile group.
It is particularly preferable to use 0.9 to 1.5 mol, and the addition of the acid is carried out at -10 ° C to 20 ° C, preferably at -5 ° C to 5 ° C or less.

【0017】前記の反応液にシアナミドを加え、引き続
きCAIM製造を行う。反応前に系内の酸を非水滴定等
で確認し、酸が過剰の場合は過剰分の酸を中和するた
め、水を副成しない塩基を添加する。pH調整用の塩基
としては、ナトリウムメチラート、ナトリウムエチラー
ト等を用いるのが好ましい。シアナミドの添加量はアセ
トニトリル1モルに対して 0.8〜2モル、好ましくは0.
9〜1.5モル、特に好ましくは0.9〜1.1モルである。
Cyanamide is added to the above reaction solution, and then CAIM is manufactured. Before the reaction, the acid in the system is checked by non-aqueous titration or the like. If the acid is excessive, a base that does not form water is added to neutralize the excess acid. As a base for adjusting pH, it is preferable to use sodium methylate, sodium ethylate and the like. The amount of cyanamide added is 0.8 to 2 mol, preferably 0.1 mol, per mol of acetonitrile.
It is 9 to 1.5 mol, particularly preferably 0.9 to 1.1 mol.

【0018】シアナミドの添加方法は特に制限されない
が、反応温度をコントロールするため、シアナミドアル
コール溶液として逐次添加するのが好ましい。シアナミ
ドを溶解する溶媒としては、工業的な実施容易性の点か
らアルコール類が好ましく、工業的規模での入手のしや
すさ、取り扱い易さから メタノール又はエタノールが
特に好ましい。
The method of adding cyanamide is not particularly limited, but it is preferable to sequentially add cyanamide alcohol as a solution to control the reaction temperature. As a solvent for dissolving cyanamide, alcohols are preferable from the viewpoint of industrial easiness, and methanol or ethanol is particularly preferable from the viewpoint of easy availability on an industrial scale and ease of handling.

【0019】反応液を20℃〜100℃ 好ましくは30℃〜5
0℃に保ちながらシアナミド溶液を添加する。反応温度
が30℃以上であれば、添加後すみやかに反応を進行させ
ることができ、反応温度が50℃以下であればシアナミド
がほとんど分解せずに反応させることができる。
The reaction solution is kept at 20 ° C. to 100 ° C., preferably 30 ° C.
Add the cyanamide solution while maintaining at 0 ° C. When the reaction temperature is 30 ° C. or higher, the reaction can proceed immediately after the addition, and when the reaction temperature is 50 ° C. or lower, the reaction can be carried out with almost no decomposition of cyanamide.

【0020】反応終了後、副成塩を分離する。分離手段
は特に制限されないが、本溶媒組成においては、溶液中
の副成塩の分散性が良いため、工業的規模においても、
容易に副成塩を分離することができる。副成塩は非極性
溶媒に対する溶解度が極めて小さいので、濾液中に溶解
している副成塩の量はわずかであり、CAIMの精留収
率を高めることができる。
After completion of the reaction, the by-product salt is separated. The separation means is not particularly limited, but in the present solvent composition, since the dispersibility of the by-product salt in the solution is good, even on an industrial scale,
By-product salts can be easily separated. Since the by-product salt has extremely low solubility in the non-polar solvent, the amount of the by-product salt dissolved in the filtrate is small, and the rectification yield of CAIM can be increased.

【0021】次いで常圧蒸留によりトルエンを回収す
る。蒸留の際には槽内温度が100℃を越えない条件、好
ましくは60℃で実施するのが良い。槽内温度が100℃を
越えない条件であれば、槽内に生成したCAIMの分解
はほとんど見られない。
Next, toluene is recovered by atmospheric distillation. The distillation is carried out at a temperature not exceeding 100 ° C., preferably at 60 ° C. If the temperature in the tank does not exceed 100 ° C., almost no decomposition of CAIM generated in the tank is observed.

【0022】留出がなくなったところで、トルエンの回
収を止めCAIMを精留により分離する。精留条件は精
留装置の構造により異なるが、精留中CAIMの分解を
防止するために釜内温度100℃を越えない温度条件で実
施するのが望ましく、留分温度50℃以下となるような
減圧条件で実施するのが特に好ましい。
When the distillation stops, the recovery of toluene is stopped and the CAIM is separated by rectification. The rectification conditions vary depending on the structure of the rectification apparatus, but it is desirable to carry out the rectification at a temperature not exceeding 100 ° C. in order to prevent the decomposition of CAIM during rectification. It is particularly preferable to carry out under a reduced pressure condition.

【0023】このようにして、反応中間体を単離するこ
となくO−アルキル−N−シアノイミデートを高収率で
製造することができる。
In this manner, O-alkyl-N-cyanoimidate can be produced in high yield without isolating the reaction intermediate.

【0024】以下実施例によりさらに本願発明を説明す
る。 実施例1 撹拌装置及び冷却装置を装備した200 CCの4つ口フラス
コにトルエン43.0g、メタノール11.6g(0.34モル)、
アセトニトリル12.4g(0.3モル)を入れ、10℃以下で
ドライ塩酸を11.6g(0.32モル)添加し、5℃で6時間反
応させる。次いで、シアナミドの50%メタノール溶液2
6.2g(0.30モル)を添加し、40℃で6時間反応させる。
その後、その反応液を5℃まで冷却し、副成した塩化ア
ンモニウムを濾過し、少量のトルエンで洗浄しCAIM反応溶液
80.6g(CAIM含有率32.3%:反応率88.3%)を得た。得
られたCAIM反応溶液を常圧から減圧下で精留し、10mmHg
/75〜78℃の留分として CAIM24.1g(純度99.8%:単離
収率81.7%)を得た。なお濾過分離した副成塩化アンモ
ニウムは、乾燥後15.3g(理論値の95.0%)であった。
Hereinafter, the present invention will be further described with reference to examples. Example 1 In a 200 CC four-necked flask equipped with a stirrer and a cooling device, 43.0 g of toluene, 11.6 g (0.34 mol) of methanol,
12.4 g (0.3 mol) of acetonitrile is added, 11.6 g (0.32 mol) of dry hydrochloric acid is added at 10 ° C. or less, and the mixture is reacted at 5 ° C. for 6 hours. Then, a 50% methanol solution of cyanamide 2
6.2 g (0.30 mol) are added and reacted at 40 ° C. for 6 hours.
Thereafter, the reaction solution was cooled to 5 ° C., ammonium chloride as a by-product was filtered, washed with a small amount of toluene, and the CAIM reaction solution was washed.
80.6 g (CAIM content: 32.3%; conversion: 88.3%) were obtained. The obtained CAIM reaction solution was rectified under reduced pressure from normal pressure to 10 mmHg
24.1 g of CAIM (purity 99.8%, isolated yield 81.7%) was obtained as a fraction at a temperature of 75/78 ° C. The amount of by-product ammonium chloride separated by filtration was 15.3 g (95.0% of the theoretical value) after drying.

【0025】実施例2 実施例1と同様な装置にトルエン43.5g、アセトニトリ
ル12.4g(0.3モル)、メタノール10.7g(0.34モル)
添加し、10℃以下でドライ塩酸を16.5g(0.45モル)を
添加し、5℃で4時間反応させる。次いで過剰の塩酸を中
和するため28%ナトリウムメチラート27.4g(0.15モ
ル)を添加した後に実施例2と同様にシアノ化反応を行
い、CAIM反応溶液101.6g(CAIM含有率26.5%:反応率9
1.5%)を得た。得られたCAIM反応溶液を常圧から減圧
下で精留し、10mmHg/75〜78℃の留分として CAIM25.2g
(純度99.5%:単離収率85.2%)を得た。なお濾過分離
した副成塩化アンモニウムは、乾燥後15.2g(理論値の
95.0%)であった。
Example 2 In the same apparatus as in Example 1, 43.5 g of toluene, 12.4 g (0.3 mol) of acetonitrile, 10.7 g (0.34 mol) of methanol
Then, 16.5 g (0.45 mol) of dry hydrochloric acid is added at 10 ° C. or lower, and the mixture is reacted at 5 ° C. for 4 hours. Next, 27.4 g (0.15 mol) of 28% sodium methylate was added to neutralize excess hydrochloric acid, and a cyanation reaction was carried out in the same manner as in Example 2. A CAIM reaction solution (101.6 g, CAIM content: 26.5%: reaction rate) 9
1.5%). The resulting CAIM reaction solution was rectified from normal pressure to reduced pressure, and 25.2 g of CAIM was obtained as a fraction of 10 mmHg / 75 to 78 ° C.
(Purity 99.5%: Isolation yield 85.2%) was obtained. The by-product ammonium chloride separated by filtration was 15.2 g after drying (theoretical value).
95.0%).

【0026】実施例3 撹拌装置及び冷却装置を装備した3Lの4つ口フラスコに
トルエン346g、メタノール106g(3.31モル)、アセト
ニトリル126.1g(3.07モル)を入れ、10℃以下でドラ
イ塩酸を112.0g(3.07モル)添加し5℃で6時間反応さ
せる。次いで、シアナミドの50%メタノール溶液260.6
g(3.07モル)を添加し、40℃で6時間反応させる。その
後、反応液を5℃まで冷却し、副成した塩化アンモニウ
ムを濾過し、CAIM溶液909.9g(CAIM含有率30.1%:反
応率91.0%)を得た。 得られたCAIM溶液を常圧から減
圧下で精留し 10mmHg/75〜78℃の留分として CAIM259.2
g(純度99.2%:単離収率86.1%)を得た。なお濾過分
離した副成塩化アンモニウムは、乾燥後 154.4g(理
論値の94%)であった。
Example 3 346 g of toluene, 106 g (3.31 mol) of methanol and 126.1 g (3.07 mol) of acetonitrile were placed in a 3 L four-necked flask equipped with a stirrer and a cooler, and 112.0 g of dry hydrochloric acid was used at 10 ° C. or lower. (3.07 mol) and react at 5 ° C for 6 hours. Next, a 50% methanol solution of cyanamide 260.6
g (3.07 mol) and react at 40 ° C. for 6 hours. Thereafter, the reaction solution was cooled to 5 ° C., and the by-product ammonium chloride was filtered to obtain 909.9 g of a CAIM solution (CAIM content: 30.1%: reaction rate: 91.0%). The resulting CAIM solution was rectified from normal pressure to reduced pressure to obtain a CAIM259.2 fraction of 10 mmHg / 75-78 ° C.
g (purity 99.2%, isolated yield 86.1%). The amount of by-product ammonium chloride separated by filtration was 154.4 g (94% of the theoretical value) after drying.

【0027】比較例1 チェコスロバキア国特許第 273050 号に記載された方法
により、O−メチルアセトイミド塩酸塩15.3g(0.14モル)
を無水メタノール20.3ml中でシアナミドと5.9g(0.14モ
ル)と反応させ,少量のメタノールで洗浄し、CAIMメタノ
ール溶液35.6g(CAIM含有率32.3%:反応率83.7%)を製
造した。副成した塩化アンモニウムを濾過し、常圧から
減圧下で精留し、 10mmHg/75〜78℃の留分として CAIM
9.8g(純度99.0%:アセトイミド塩酸塩からの単離収率
70.6% )を得た。なお濾過分離した副成塩化アンモニ
ウムは、乾燥後5.4g(理論値の86.1%)であった。
Comparative Example 1 15.3 g (0.14 mol) of O-methylacetimide hydrochloride was prepared according to the method described in Czechoslovak Patent No. 273050.
Was reacted with 5.9 g (0.14 mol) of cyanamide in 20.3 ml of anhydrous methanol and washed with a small amount of methanol to produce 35.6 g of a CAIM methanol solution (CAIM content: 32.3%; conversion: 83.7%). The by-product ammonium chloride was filtered, rectified under normal pressure to reduced pressure, and distilled at 10 mmHg / 75-78 ° C as CAIM.
9.8 g (purity 99.0%: isolation yield from acetimide hydrochloride)
70.6%). The amount of by-product ammonium chloride separated by filtration was 5.4 g (86.1% of the theoretical value) after drying.

Claims (2)

【特許請求の範囲】[Claims] 【請求項1】ニトリル基を有する化合物とアルコールと
を酸の存在下非極性溶媒中で反応させ、次いで得られる
反応液にシアナミドを加え加熱することを特徴とするO
−アルキル−N−シアノイミデートの製造方法。
1. A method comprising reacting a compound having a nitrile group with an alcohol in the presence of an acid in a non-polar solvent, adding cyanamide to the resulting reaction solution and heating the mixture.
A method for producing an alkyl-N-cyanoimidate.
【請求項2】アセトニトリルとメタノールを酸の存在下
非極性溶媒中で反応させ、得られた反応液にシアナミド
を加えて加熱することを特徴とする請求項1記載のO−
メチル−N−シアノアセトイミデートの製造方法。
2. The method according to claim 1, wherein acetonitrile and methanol are reacted in a nonpolar solvent in the presence of an acid, and cyanamide is added to the resulting reaction solution and heated.
A method for producing methyl-N-cyanoacetimidate.
JP23581696A 1996-08-20 1996-08-20 Process for producing O-alkyl-N-cyanoimidate Expired - Fee Related JP3306312B2 (en)

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Application Number Priority Date Filing Date Title
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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1113002A1 (en) * 1998-09-09 2001-07-04 Nippon Carbide Kogyo Kabushiki Kaisha Process for producing o-alkyl-n-cyanoimidate
CN110256295A (en) * 2019-07-03 2019-09-20 宁夏贝利特生物科技有限公司 The synthetic method of N- cyan ethyl ethylimidoote

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1113002A1 (en) * 1998-09-09 2001-07-04 Nippon Carbide Kogyo Kabushiki Kaisha Process for producing o-alkyl-n-cyanoimidate
EP1113002A4 (en) * 1998-09-09 2003-01-02 Nippon Carbide Kogyo Kk Process for producing o-alkyl-n-cyanoimidate
US6613925B1 (en) 1998-09-09 2003-09-02 Nippon Carbide Kogyo K.K. Process for producing O-alkyl-N-cyanoimidate
CN110256295A (en) * 2019-07-03 2019-09-20 宁夏贝利特生物科技有限公司 The synthetic method of N- cyan ethyl ethylimidoote

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