JPH035390B2 - - Google Patents
Info
- Publication number
- JPH035390B2 JPH035390B2 JP22333583A JP22333583A JPH035390B2 JP H035390 B2 JPH035390 B2 JP H035390B2 JP 22333583 A JP22333583 A JP 22333583A JP 22333583 A JP22333583 A JP 22333583A JP H035390 B2 JPH035390 B2 JP H035390B2
- Authority
- JP
- Japan
- Prior art keywords
- aminoisoxazole
- reaction
- present
- hydroxylamine
- sodium hydroxide
- 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
- IAXWZYXUKABJAN-UHFFFAOYSA-N 1,2-oxazol-5-amine Chemical compound NC1=CC=NO1 IAXWZYXUKABJAN-UHFFFAOYSA-N 0.000 claims description 14
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 9
- 238000004519 manufacturing process Methods 0.000 claims description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 8
- IPCRTSDORDQHRO-DUXPYHPUSA-N (e)-3-methoxyprop-2-enenitrile Chemical compound CO\C=C\C#N IPCRTSDORDQHRO-DUXPYHPUSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000002585 base Substances 0.000 description 5
- 239000013078 crystal Substances 0.000 description 5
- 239000002994 raw material Substances 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- ZKKBIZXAEDFPNL-UHFFFAOYSA-N 3-(dimethylamino)prop-2-enenitrile Chemical compound CN(C)C=CC#N ZKKBIZXAEDFPNL-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 229910001385 heavy metal Inorganic materials 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- RHFWLPWDOYJEAL-UHFFFAOYSA-N 1,2-oxazol-3-amine Chemical compound NC=1C=CON=1 RHFWLPWDOYJEAL-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- OKWZLGRVRIJPKN-UHFFFAOYSA-N 2-butoxyprop-2-enenitrile Chemical compound C(CCC)OC(C#N)=C OKWZLGRVRIJPKN-UHFFFAOYSA-N 0.000 description 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-M 2-methylbenzenesulfonate Chemical compound CC1=CC=CC=C1S([O-])(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-M 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- AGSPXMVUFBBBMO-UHFFFAOYSA-N beta-aminopropionitrile Chemical compound NCCC#N AGSPXMVUFBBBMO-UHFFFAOYSA-N 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000002443 hydroxylamines Chemical class 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- XGZVUEUWXADBQD-UHFFFAOYSA-L lithium carbonate Chemical compound [Li+].[Li+].[O-]C([O-])=O XGZVUEUWXADBQD-UHFFFAOYSA-L 0.000 description 1
- 229910052808 lithium carbonate Inorganic materials 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- -1 n-octyl Chemical group 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- XMVONEAAOPAGAO-UHFFFAOYSA-N sodium tungstate Chemical compound [Na+].[Na+].[O-][W]([O-])(=O)=O XMVONEAAOPAGAO-UHFFFAOYSA-N 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
Landscapes
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Description
【発明の詳細な説明】
本発明は、５−アミノイソオキサゾールの新規
な製法に関するものである。さらに詳しくは、３
−アルコキシアクリロニトリルとヒドロキシアミ
ンを反応させる５−アミノイソオキサゾールの新
規な製法に関するものである。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a novel method for producing 5-aminoisoxazole. For more details, see 3.
This invention relates to a novel method for producing 5-aminoisoxazole by reacting -alkoxyacrylonitrile with hydroxyamine.
５−アミノイソオキサゾールは、例えば医薬、
農薬などの原料として有用な化合物であり、以前
からその製法について種々提案がなされている。 5-Aminoisoxazole can be used, for example, in pharmaceuticals,
It is a compound that is useful as a raw material for agricultural chemicals, and various proposals have been made for its production.
例えば特公昭44−16898号公報には、β−アミ
ノプロピオニトリルと過酸化水を反応させる、５
−アミノイソオキサゾールの製法につき提案され
いる。この方法は、目的物の収率が高40％程度と
極め低いばかりか、タングステン酸ナトリウムな
どの重金属系触媒が使用されるため、反応後目的
物と触媒との分離操作を必要とし、また廃水中に
重金属が含まれる恐れもある、など工業的に多く
の問題点を有している。 For example, Japanese Patent Publication No. 44-16898 discloses a method of reacting β-aminopropionitrile with water peroxide.
- A method for producing aminoisoxazole is proposed. This method not only has a very low yield of the target product at around 40%, but also uses a heavy metal catalyst such as sodium tungstate, which requires separation between the target product and the catalyst after the reaction. It has many industrial problems, including the possibility that it may contain heavy metals.
また米国特許第3709922号明細書には、β−ジ
メチルアミノアクリロニトリルとヒドロキシルア
ミン塩酸塩を、ジメチルホルムアミド中で反応さ
せる５−アミノイソオキサゾールの製法につき提
案がなされている。この方法は、原料のβ−ジメ
チルアミノアクリロニトリルが極めて高価である
という欠点を有している。 Further, US Pat. No. 3,709,922 proposes a method for producing 5-aminoisoxazole in which β-dimethylaminoacrylonitrile and hydroxylamine hydrochloride are reacted in dimethylformamide. This method has the disadvantage that the raw material β-dimethylaminoacrylonitrile is extremely expensive.
本発明者らは、５−アミノイソオキサゾールの
工業的有利な製法を開発することを目的とし、鋭
意研究を行つた。その結果、安価に容易に入手で
きる３−アルコキシアクリロニトリルとヒドロキ
シアミン反応させれば、何ら触媒を用いることな
く高収率にて５−アミノイソオキサゾールを合成
できることを見い出し、本発明を完成するに到つ
た。 The present inventors conducted extensive research with the aim of developing an industrially advantageous manufacturing method for 5-aminoisoxazole. As a result, they discovered that 5-aminoisoxazole can be synthesized in high yield without using any catalyst by reacting 3-alkoxyacrylonitrile, which is easily available at low cost, with hydroxyamine, and have completed the present invention. Ivy.
本発明の原料である３−アルコキシアクリロニ
トリルは、一般式ROCH＝CHCNで示すことが
できる。該式において、Ｒはメチル、エチル、ｎ
−プロピル、ｉ−プロピル、ｎ−ブチル、ｉ−ブ
チル、sec−ブチル、tert−ブチル、ｎ−ペンチ
ル、ｎ−ヘキシル、ｎ−ヘプチル、ｎ−オクチル
などの如き炭素数１〜８を有するアルキル基を挙
げることができる。これらのアルキル基には、反
応を阻害しない置換基、例えばアルコキシ基、ハ
ロゲン原子などの置換基を有すこともできる。 3-alkoxyacrylonitrile, which is a raw material of the present invention, can be represented by the general formula ROCH=CHCN. In this formula, R is methyl, ethyl, n
- Alkyl groups having 1 to 8 carbon atoms such as propyl, i-propyl, n-butyl, i-butyl, sec-butyl, tert-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, etc. can be mentioned. These alkyl groups may also have a substituent that does not inhibit the reaction, such as an alkoxy group or a halogen atom.
本発明のもう一つの原料であるヒドロキシアミ
ンは、それ自体でもよいが、通常、硫酸塩、塩酸
塩、硝酸塩、リン酸塩、酢酸塩あるいはトルエン
スルホン酸塩などの塩の形で使用に供される。そ
の使用量は、３−アルコキシアクリロニトリル１
モルに対して、0.1〜10モル、好ましくは0.5〜５
モルである。 Hydroxyamine, which is another raw material of the present invention, may be used as such, but it is usually used in the form of a salt such as sulfate, hydrochloride, nitrate, phosphate, acetate, or toluenesulfonate. Ru. The amount used is 3-alkoxyacrylonitrile 1
0.1 to 10 moles, preferably 0.5 to 5 moles
It is a mole.
前記ヒドロキシルアミンの塩を使用する場合に
は、塩基を用いて遊離のヒドロキシルアミンを形
成させる必要がある。この目的に使用される塩基
としては、水酸化ナトリウム、水酸化カリウムな
どのアルカリ金属の水酸化物、炭酸ナトリウム、
炭酸水素ナトリウム、炭酸カリウム、炭酸リチウ
ムなどのアルカリ金属の（重）炭酸塩、あるいは
トリエチルアミン、ピリジンなどの３級アミン、
などが挙げられる。なお本発明では、反応系に塩
基が存在した場合、目的物の収率が低下する傾向
にある。従つて、前記塩基はヒドロキシルアミン
の塩とほぼ等モルかあるいはそれ以下の量を使用
し、形成されるヒドロキシルアミン水溶液中に過
剰の塩基が存在しないようにすることが望まれ
る。 If a salt of the hydroxylamine is used, it is necessary to use a base to form free hydroxylamine. Bases used for this purpose include alkali metal hydroxides such as sodium hydroxide, potassium hydroxide, sodium carbonate,
Alkali metal (bi)carbonates such as sodium hydrogen carbonate, potassium carbonate, and lithium carbonate, or tertiary amines such as triethylamine and pyridine;
Examples include. In the present invention, when a base is present in the reaction system, the yield of the target product tends to decrease. Therefore, it is desirable to use the base in an amount that is approximately equimolar or less than that of the hydroxylamine salt so that an excess base is not present in the aqueous hydroxylamine solution that is formed.
本発明の反応は、原料をよく溶かし反応を阻害
しない溶媒中で行われる。その溶媒としては、例
えば水、メタノール、エタノール、ジオキサン、
ジメチルホルムアミドなどが挙げられる。 The reaction of the present invention is carried out in a solvent that dissolves the raw materials well and does not inhibit the reaction. Examples of the solvent include water, methanol, ethanol, dioxane,
Examples include dimethylformamide.
本発明の反応は、室温程度の温和な条件でも反
応は進行するが、加熱によつて反応速度を高める
こともできる。通常、反応は10〜150℃の温度で
0.5〜10時間行うことによつて、完結する。 Although the reaction of the present invention proceeds under mild conditions at about room temperature, the reaction rate can also be increased by heating. Usually the reaction is carried out at a temperature of 10-150℃
It can be completed by doing it for 0.5 to 10 hours.
反応後、蒸留、過、抽出あるいはクロマトグ
ラフイーなどの操作を適宜行うことにより、目的
物の５−アミノイソオキサゾールを単離、取得す
ることができる。 After the reaction, the target product, 5-aminoisoxazole, can be isolated and obtained by appropriately performing operations such as distillation, filtration, extraction, or chromatography.
次に、本発明の実施例を挙げる。 Next, examples of the present invention will be given.
実施例 １
冷却器、温度計および滴下ロートをつけた内容
積50mlの三ツ口フラスコに、ヒドロキシルアミン
塩酸塩8.4gを仕込み、次いで水10mlと水酸化ナト
リウム4.8gより調製した水酸化ナトリウム水溶液
を滴下した。撹拌下に、３−メトキシアクリロニ
トリル8.3gを滴下し、約80℃で３時間反応を行つ
た後、反応物を冷却し酢酸エチルで３回抽出し
た。酢酸エチル層を無水硫酸ナトリウムで乾燥し
た後、減圧下で酢酸エチルを留去し、7.95gの茶
色の液体を得た。該液体をシリカゲルカラムクロ
マトにより分離し、うす黄色の液体5.3gを得、こ
の液体はしばらく放置すると結晶化した。該結晶
は、NMR，IR，MSスペクトルより５−アミノ
イソオキサゾールであることを確認した。Example 1 8.4 g of hydroxylamine hydrochloride was placed in a 50 ml three-necked flask equipped with a condenser, thermometer, and dropping funnel, and then an aqueous sodium hydroxide solution prepared from 10 ml of water and 4.8 g of sodium hydroxide was added dropwise. . While stirring, 8.3 g of 3-methoxyacrylonitrile was added dropwise and the reaction was carried out at about 80° C. for 3 hours, after which the reaction mixture was cooled and extracted three times with ethyl acetate. After drying the ethyl acetate layer over anhydrous sodium sulfate, ethyl acetate was distilled off under reduced pressure to obtain 7.95 g of a brown liquid. The liquid was separated by silica gel column chromatography to obtain 5.3 g of a pale yellow liquid, which crystallized upon standing for a while. The crystals were confirmed to be 5-aminoisoxazole by NMR, IR, and MS spectra.
実施例 ２
冷却器、温度計および滴下ロートをつけた内容
積100mlの三ツ口フラスコに、ヒドロキシルアミ
ン塩酸塩8.4gを仕込み、次いで水20mlと水酸化ナ
トリウム4.8gより調製した水酸化ナトリウム水溶
液を滴下した。撹拌下に、３−メトキシアクリロ
ニトリル8.3gを滴下し、約60℃で３時間反応を行
つた後、反応物を冷却し酢酸エチルで３回抽出し
た。酢酸エチル層を無水硫酸ナトリウムで乾燥し
た後、減圧蒸留し90〜100℃／３mmHgの留分4.8g
を得た。この留分は、蒸留中冷却管出口で直ちに
結晶化し、NMR，IR，MSスペクトルによりほ
ぼ純粋な５−アミノイソオキサゾールであること
が確認された。Example 2 8.4 g of hydroxylamine hydrochloride was placed in a 100 ml three-necked flask equipped with a condenser, thermometer, and dropping funnel, and then an aqueous sodium hydroxide solution prepared from 20 ml of water and 4.8 g of sodium hydroxide was added dropwise. . While stirring, 8.3 g of 3-methoxyacrylonitrile was added dropwise and the reaction was carried out at about 60° C. for 3 hours. The reaction mixture was then cooled and extracted three times with ethyl acetate. After drying the ethyl acetate layer over anhydrous sodium sulfate, it was distilled under reduced pressure to obtain 4.8g of fraction at 90-100℃/3mmHg.
I got it. This fraction crystallized immediately at the outlet of the cooling tube during distillation, and was confirmed by NMR, IR, and MS spectra to be almost pure 5-aminoisoxazole.
実施例 ３
冷却器、温度計、滴下ロートをつけた内容積１
の三ツ口フラスコに、99.6gの３−メトキシア
クリロニトリルを仕込んだ。撹拌下、内温が60℃
を越えないようにしながら、ヒドロキシルアミン
水溶液（ヒドロキシルアミン塩酸塩100.1gに、
57.6gの水酸化ナトリウムと250mlの水より調製し
た水酸化ナトリウム水溶液をヒドロキシルアミン
水溶液がPH７となるまで加えて調製したもの。）
を１時間を要して滴下した後、約60℃で1.5時間
撹拌した。次いで冷却後、酢酸エチルで３回抽出
した。酢酸エチル層を無水硫酸ナトリウムで乾燥
した後、減圧下で濃縮、冷却し、析出した５−ア
ミノイソオキサゾールの粗結晶47.6gを集した。Example 3 Internal volume 1 with cooler, thermometer and dropping funnel
99.6 g of 3-methoxyacrylonitrile was charged into a three-necked flask. Under stirring, internal temperature is 60℃
Add hydroxylamine aqueous solution (100.1g of hydroxylamine hydrochloride to
Prepared by adding a sodium hydroxide aqueous solution prepared from 57.6g of sodium hydroxide and 250ml of water until the hydroxylamine aqueous solution reaches pH 7. )
was added dropwise over a period of 1 hour, and then stirred at about 60°C for 1.5 hours. After cooling, the mixture was extracted three times with ethyl acetate. The ethyl acetate layer was dried over anhydrous sodium sulfate, concentrated under reduced pressure and cooled, and 47.6 g of precipitated crude crystals of 5-aminoisoxazole were collected.
実施例 ４
３−メトキシアクリロニトリル8.3gを20mlのメ
タノールに溶かし、該溶液を反応系に滴下した他
は、実施例２と同様の操作で実験を行つた。その
結果、５−アミノイソオキサゾールの粗結晶が、
5.9g得られた。Example 4 An experiment was carried out in the same manner as in Example 2, except that 8.3 g of 3-methoxyacrylonitrile was dissolved in 20 ml of methanol, and the solution was added dropwise to the reaction system. As a result, the crude crystals of 5-aminoisoxazole were
5.9g was obtained.
実施例 ５
３−メトキシアクリロニトリルに代えて、３−
ｎ−ブトキシアクリロニトリル12.5gを用いた他
は、実施例４と同様の操作で実験を行つた。その
結果、５−アミノイソオキサゾールの粗結晶が
5.5g得られた。Example 5 Instead of 3-methoxyacrylonitrile, 3-
An experiment was conducted in the same manner as in Example 4, except that 12.5 g of n-butoxyacrylonitrile was used. As a result, crude crystals of 5-aminoisoxazole were obtained.
5.5g was obtained.
実施例 ６
水酸化ナトリウムに代えて炭酸カリウム8.3gを
用い、また３−メトキシアクリロニトリル8.3gを
20mlのジメチルホルムアミドに溶かし、該溶液を
反応系に滴下した他は、実施例２と同様の操作で
実験を行つた。その結果、５−アミノイソオキサ
ゾールの粗結晶が3.8g得られた。Example 6 8.3g of potassium carbonate was used instead of sodium hydroxide, and 8.3g of 3-methoxyacrylonitrile was used.
An experiment was conducted in the same manner as in Example 2, except that it was dissolved in 20 ml of dimethylformamide and the solution was added dropwise to the reaction system. As a result, 3.8 g of crude crystals of 5-aminoisoxazole were obtained.
Claims (1)
シアミンを反応させることを特徴とする５−アミ
ノイソオキサゾールの製法。1. A method for producing 5-aminoisoxazole, which comprises reacting 3-alkoxyacrylonitrile with hydroxyamine.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP22333583A JPS60116674A (en) | 1983-11-29 | 1983-11-29 | Production of 5-aminoisoxazole |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP22333583A JPS60116674A (en) | 1983-11-29 | 1983-11-29 | Production of 5-aminoisoxazole |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS60116674A JPS60116674A (en) | 1985-06-24 |
| JPH035390B2 true JPH035390B2 (en) | 1991-01-25 |
Family
ID=16796541
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP22333583A Granted JPS60116674A (en) | 1983-11-29 | 1983-11-29 | Production of 5-aminoisoxazole |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS60116674A (en) |
-
1983
- 1983-11-29 JP JP22333583A patent/JPS60116674A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS60116674A (en) | 1985-06-24 |
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