JPH0446266B2 - - Google Patents
Info
- Publication number
- JPH0446266B2 JPH0446266B2 JP58077599A JP7759983A JPH0446266B2 JP H0446266 B2 JPH0446266 B2 JP H0446266B2 JP 58077599 A JP58077599 A JP 58077599A JP 7759983 A JP7759983 A JP 7759983A JP H0446266 B2 JPH0446266 B2 JP H0446266B2
- Authority
- JP
- Japan
- Prior art keywords
- formula
- represented
- oxamidic
- mixture
- crystals
- 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 - Lifetime
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
【発明の詳細な説明】
この発明は、新規化合物であるオキサミド酸
（ホルミルヒドラジド）およびその製造法に関す
る。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a novel compound, oxamidic acid (formylhydrazide), and a method for producing the same.
新規なオキサミド酸（ホルミルヒドラジド）は
式
で表わされ、
式
（式中、Ｒは炭素数１〜４のアルキル基を示
す。）で表わされるオキサミド酸エステルとホル
ミルヒドラジンとを反応させることによつて製造
することができる。 The novel oxamidic acid (formyl hydrazide) has the formula It is represented by the formula (In the formula, R represents an alkyl group having 1 to 4 carbon atoms.) It can be produced by reacting an oxamic acid ester represented by the following formula with formylhydrazine.
式〔〕で表わされるオキサミド酸エステルの
具体例としては、オキサミド酸メチル、オキサミ
ド酸エチル、オキサミド酸プロピル、オキサミド
酸ブチルが挙げられる。 Specific examples of the oxamate ester represented by the formula [] include methyl oxamate, ethyl oxamate, propyl oxamate, and butyl oxamate.
反応は、オキサミド酸エステルとホルミルヒド
ラジンの当モル混合物を、120〜10℃の温度範囲
で、１〜２時間加熱することによつて、定量的に
行なわれる。 The reaction is carried out quantitatively by heating an equimolar mixture of oxamic acid ester and formylhydrazine at a temperature range of 120 to 10°C for 1 to 2 hours.
反応後の反応生成混合物中には、目的物のオキ
サミド酸（ホルミルヒドラジド）と副生成物のオ
キサミド酸エステルに由来するアルコールとが存
在する。目的物のオキサミド酸（ホルミルヒドラ
ジド）は、通常の有機溶媒に難溶の結晶であり、
反応生成混合物を蒸留あるいは過などの方法に
よつて処理して、反応生成混合物から液体である
副生成物のアルコールを分離することによつて、
単離することができる。 The reaction product mixture after the reaction contains the target oxamic acid (formyl hydrazide) and the alcohol derived from the oxamic acid ester as a by-product. The target oxamidic acid (formyl hydrazide) is a crystal that is poorly soluble in ordinary organic solvents.
By treating the reaction product mixture by a method such as distillation or filtration to separate the liquid by-product alcohol from the reaction product mixture,
Can be isolated.
この発明のオキサミド酸（ホルミルヒドラジ
ド）は、製薬の分野において、有機合成用の価値
ある出発化合物である。たとえば、ホルムアミド
中、アンモニアあるいはカルボン酸アンモニウム
と処理することによつて、医薬中間体として有用
な１，２，４−トリアゾール−３−カルボン酸ア
ミドを得ることができる。１，２，４−トリアゾ
ール−３−カルボン酸アミドは、リボースリン酸
エステルの存在で酵素ヌクレオシドホスホリラー
ゼと反応させることによつて、１−β−Ｄ−リボ
フラノシル−１，２，４−トリアゾール−３−カ
ルボン酸アミドとすることができ、これはインフ
ルエンザウイルス感染症に有効である。 The oxamidic acids (formyl hydrazides) of this invention are valuable starting compounds for organic synthesis in the pharmaceutical field. For example, by treatment with ammonia or ammonium carboxylate in formamide, 1,2,4-triazole-3-carboxylic acid amide useful as a pharmaceutical intermediate can be obtained. 1,2,4-triazole-3-carboxylic acid amide is prepared by reacting with the enzyme nucleoside phosphorylase in the presence of ribose phosphate to form 1-β-D-ribofuranosyl-1,2,4-triazole-3- It can be a carboxylic acid amide, which is effective against influenza virus infections.
つぎに実施例を示す。 Next, examples will be shown.
実施例 １
オキサミド酸エチル11.71ｇとホルミルヒドラ
ジン6.01ｇの混合物を145〜150℃の油浴上で加熱
して、25分間反応させた。混合物を加熱すると、
均一溶液となつたのち、新たな結晶が生成し、こ
の間副生したエタノールは還流させた。Example 1 A mixture of 11.71 g of ethyl oxamate and 6.01 g of formylhydrazine was heated on an oil bath at 145 to 150°C and reacted for 25 minutes. When the mixture is heated,
After becoming a homogeneous solution, new crystals were formed, and during this time the by-produced ethanol was refluxed.
反応後、得られた反応生成混合物を室温まで冷
却したのち、エタノール25mlを加えて過し、オ
キサミド酸（ホルミルヒドラジド）の結晶12.66
ｇを得た。これを水で再結晶して、分解点269℃
の無色結晶を得た。その元素分析値をつぎに、赤
外線吸収スペクトルを図１に示す。 After the reaction, the resulting reaction product mixture was cooled to room temperature, and 25 ml of ethanol was added and filtered to give 12.66 mL of crystals of oxamic acid (formyl hydrazide).
I got g. This is recrystallized with water and has a decomposition point of 269℃.
Colorless crystals were obtained. The elemental analysis values and infrared absorption spectrum are shown in FIG.
Ｃ Ｈ Ｎ
分析値 27.29 3.56 32.41
計算値 27.49 3.84 32.05
（C3H5N3O3として）
実施例 ２
オキサミド酸（ホルミルヒドラジド）1.31ｇ、
酢酸アンモニウム0.77ｇとホルムアミド30mlの混
合物を150℃の油浴上で加熱して、１時間反応さ
せた。 C H N Analytical value 27.29 3.56 32.41 Calculated value 27.49 3.84 32.05 (as C 3 H 5 N 3 O 3 ) Example 2 Oxamidic acid (formyl hydrazide) 1.31 g,
A mixture of 0.77 g of ammonium acetate and 30 ml of formamide was heated on an oil bath at 150° C. and reacted for 1 hour.
反応後、得られた反応生成混合物を室温まで冷
却したのち過して、オキサミドの結晶0.45ｇを
得た。液を減圧下に濃縮し、残渣に水30mlを加
えて過した。得られた結晶を濃アンモニア水20
mlに加えて、混合物を室温で１時間撹拌したのち
過して、オキサミドの結晶0.01ｇを得た。液
を減圧下に濃縮して、１，２，４−トリアゾール
−３−カルボン酸アミドの結晶0.14ｇを得た。 After the reaction, the resulting reaction product mixture was cooled to room temperature and filtered to obtain 0.45 g of oxamide crystals. The liquid was concentrated under reduced pressure, and 30 ml of water was added to the residue and filtered. Pour the obtained crystals into concentrated ammonia water for 20 minutes.
ml, the mixture was stirred at room temperature for 1 hour and then filtered to yield 0.01 g of oxamide crystals. The liquid was concentrated under reduced pressure to obtain 0.14 g of crystals of 1,2,4-triazole-3-carboxylic acid amide.
第１図は実施例１で得られたオキサミド酸（ホ
ルミルヒドラジド）の赤外吸収スペクトル図であ
る。
FIG. 1 is an infrared absorption spectrum diagram of oxamidic acid (formyl hydrazide) obtained in Example 1.
Claims (1)
ド）。 ２ 式 （式中、Ｒは炭素数１〜４のアルキル基を示
す。）で表わされるオキサミド酸エステルとホル
ミルヒドラジンとを反応させることを特徴とする 式 で表わされるオキサミド酸（ホルミルヒドラジ
ド）の製造法。[Claims] 1 formula Oxamidic acid (formyl hydrazide) represented by 2 formulas (In the formula, R represents an alkyl group having 1 to 4 carbon atoms.) A formula characterized by reacting an oxamic acid ester represented by the following formula with formylhydrazine. A method for producing oxamic acid (formyl hydrazide) represented by
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP7759983A JPS59204162A (en) | 1983-05-04 | 1983-05-04 | Oxamic acid (formyl hydrazide) and production thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP7759983A JPS59204162A (en) | 1983-05-04 | 1983-05-04 | Oxamic acid (formyl hydrazide) and production thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS59204162A JPS59204162A (en) | 1984-11-19 |
| JPH0446266B2 true JPH0446266B2 (en) | 1992-07-29 |
Family
ID=13638404
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP7759983A Granted JPS59204162A (en) | 1983-05-04 | 1983-05-04 | Oxamic acid (formyl hydrazide) and production thereof |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS59204162A (en) |
-
1983
- 1983-05-04 JP JP7759983A patent/JPS59204162A/en active Granted
Non-Patent Citations (1)
| Title |
|---|
| CHIM ACTA TURC=1974 * |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS59204162A (en) | 1984-11-19 |
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