JPH0449546B2 - - Google Patents
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- Publication number
- JPH0449546B2 JPH0449546B2 JP14247483A JP14247483A JPH0449546B2 JP H0449546 B2 JPH0449546 B2 JP H0449546B2 JP 14247483 A JP14247483 A JP 14247483A JP 14247483 A JP14247483 A JP 14247483A JP H0449546 B2 JPH0449546 B2 JP H0449546B2
- Authority
- JP
- Japan
- Prior art keywords
- amino
- reaction
- oxo
- formula
- present
- 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
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- 238000006243 chemical reaction Methods 0.000 claims description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 8
- 150000001875 compounds Chemical class 0.000 claims description 7
- LETZBFFXEPHDOU-UHFFFAOYSA-N 2-oxo-1,3-oxazolidine-4-carbonitrile Chemical class O=C1NC(C#N)CO1 LETZBFFXEPHDOU-UHFFFAOYSA-N 0.000 claims description 6
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 claims description 5
- 229910052783 alkali metal Inorganic materials 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 150000001340 alkali metals Chemical class 0.000 claims description 3
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 3
- 150000004649 carbonic acid derivatives Chemical class 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 239000003125 aqueous solvent Substances 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims 1
- -1 2-oxo-4-cyanooxazolines Chemical class 0.000 description 9
- 238000000034 method Methods 0.000 description 6
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
- WNFAWINJBNDQLB-UHFFFAOYSA-N 2-amino-3-chloropropanenitrile Chemical compound ClCC(N)C#N WNFAWINJBNDQLB-UHFFFAOYSA-N 0.000 description 3
- HISPVKYXAHOFSZ-UHFFFAOYSA-N 2-amino-3-chloropropanenitrile;hydrochloride Chemical compound Cl.ClCC(N)C#N HISPVKYXAHOFSZ-UHFFFAOYSA-N 0.000 description 3
- 239000001099 ammonium carbonate Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 description 2
- ATRRKUHOCOJYRX-UHFFFAOYSA-N Ammonium bicarbonate Chemical compound [NH4+].OC([O-])=O ATRRKUHOCOJYRX-UHFFFAOYSA-N 0.000 description 2
- 229910000013 Ammonium bicarbonate Inorganic materials 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 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
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 235000008206 alpha-amino acids Nutrition 0.000 description 2
- 235000012538 ammonium bicarbonate Nutrition 0.000 description 2
- 150000003863 ammonium salts Chemical class 0.000 description 2
- 239000001569 carbon dioxide Substances 0.000 description 2
- 229910002092 carbon dioxide Inorganic materials 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- MTCFGRXMJLQNBG-UHFFFAOYSA-N Serine Natural products OCC(N)C(O)=O MTCFGRXMJLQNBG-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 150000001370 alpha-amino acid derivatives Chemical class 0.000 description 1
- 150000001371 alpha-amino acids Chemical class 0.000 description 1
- 235000012501 ammonium carbonate Nutrition 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- JYYOBHFYCIDXHH-UHFFFAOYSA-N carbonic acid;hydrate Chemical compound O.OC(O)=O JYYOBHFYCIDXHH-UHFFFAOYSA-N 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- QHDRKFYEGYYIIK-UHFFFAOYSA-N isovaleronitrile Chemical compound CC(C)CC#N QHDRKFYEGYYIIK-UHFFFAOYSA-N 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229960003975 potassium Drugs 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 229940086066 potassium hydrogencarbonate Drugs 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 150000003839 salts Chemical group 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 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
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
Description
【発明の詳細な説明】
本発明は一般式
（式中、R1，R2およびR3はそれぞれ水素原子
または低級アルキル基を表わす。）にて表わされ
る２−オキソ−４−シアノオキサゾリン類の製造
方法に関する。[Detailed Description of the Invention] The present invention relates to the general formula (In the formula, R 1 , R 2 and R 3 each represent a hydrogen atom or a lower alkyl group.) The present invention relates to a method for producing 2-oxo-4-cyanooxazolines represented by the formula:
本発明の上記一般式にて表わされる２−オキソ
−４−シアノオキサゾリジン類はα−アミノ酸や
医薬、農薬等の合成用中間体として有用な化合物
であり、例えば、２−オキソ−４−シアノオキサ
ゾリジンを酸で加水分解すると、α−アミノ酸の
一種であるセリンを得ることができる。 The 2-oxo-4-cyanooxazolidines represented by the above general formula of the present invention are compounds useful as intermediates for the synthesis of α-amino acids, medicines, agricultural chemicals, etc. For example, 2-oxo-4-cyanooxazolidine When hydrolyzed with acid, serine, which is a type of α-amino acid, can be obtained.
本発明者らはこの２−オキソ−４−シアノオキ
サゾリン類の工業的な製造法に関して種々検討し
た結果、一般式
（式中、Ｘはハロゲン原子を表わし、R1，R2
およびR3は上記と同じ。）にて表わされるα−ア
ミノ−β−ハロゲノニトリル化合物を水または水
性溶媒中で、アルカリ金属、アルカリ土類金属ま
たはアンモニウムの炭酸塩または炭酸水素塩と反
応させることにより目的物を高収率で得ることが
できることを見い出し、本発明の方法を完成する
に至つた。 As a result of various studies conducted by the present inventors regarding the industrial production method of these 2-oxo-4-cyanooxazolines, the general formula (In the formula, X represents a halogen atom, R 1 , R 2
and R 3 are the same as above. ) The target compound can be obtained in high yield by reacting the α-amino-β-halogenonitrile compound represented by The inventors have discovered that the method of the present invention can be obtained, and have completed the method of the present invention.
本発明の方法は、従来全く知られていない新規
な製造法であり１）安価な原料の使用で該化合物
を製造しうる２）反応条件がゆるやかであり、操
作が容易である３）高収率で該化合物が得られる
等の利点を有し工業的に非常に有用な製造方法で
ある。 The method of the present invention is a novel production method that has not been previously known. 1) The compound can be produced using inexpensive raw materials. 2) The reaction conditions are mild and the operation is easy. 3) It has a high yield. This is an industrially very useful production method, as it has advantages such as the ability to obtain the compound at a relatively low yield.
本発明の方法で用いる前記一般式で表わされる
α−アミノβハロゲノニトリル類の具体例として
代表的なものを示せば、例えば、２−アミノ−３
−ハロゲノ−プロピオニトリル，２−アミノ−３
−ハロゲノブチロニトリル，２−アミノ，３−ハ
ロゲノ，３−メチルブチロニトリル，２−アミ
ノ，３−ハロゲノバレロニトリル等が挙げられ
る。またハロゲン原子としては塩素または臭素が
用いられる。これらの原料は、例えば、対応する
αハロゲノアルデヒドから製造することが出来
る。使用する形態としては特に制限はなく、遊離
形、鉱酸塩、のいずれの形でも使用出来る。 Typical specific examples of α-amino β halogenonitriles represented by the above general formula used in the method of the present invention include, for example, 2-amino-3
-halogeno-propionitrile, 2-amino-3
-halogenobutyronitrile, 2-amino, 3-halogeno, 3-methylbutyronitrile, 2-amino, 3-halogenovaleronitrile, and the like. Moreover, chlorine or bromine is used as the halogen atom. These raw materials can be produced, for example, from the corresponding α-halogenaldehydes. There are no particular restrictions on the form used, and either free form or mineral salt form can be used.
一方、他の原料である炭酸塩または炭酸水素塩
としてはリチウム、ナトリウム、カリウム等のア
ルカリ金属塩、カルシウム、マグネシウム等のア
ルカリ土類金属塩またはアンモニウム塩が用いら
れ、殊に重炭酸塩の場合にはいずれでも良いが、
炭酸塩の場合にはアルカリ金属またはアンモニウ
ムの塩が好ましい。また、炭酸塩または炭酸水素
塩を直接用いること以外にも、例えば、アルカリ
金属、アルカリ土類金属またはアンモニウムの水
酸化物または炭酸塩の溶解液または懸濁液に二酸
化炭素ガスを吹込んだものに前記原料化合物を添
加して反応させても良い。 On the other hand, as the other raw material carbonate or hydrogen carbonate, alkali metal salts such as lithium, sodium, and potassium, alkaline earth metal salts such as calcium and magnesium, or ammonium salts are used, especially in the case of bicarbonate. Either is fine for
In the case of carbonates, alkali metal or ammonium salts are preferred. In addition to directly using carbonates or hydrogen carbonates, for example, carbon dioxide gas may be blown into a solution or suspension of an alkali metal, alkaline earth metal, or ammonium hydroxide or carbonate. The above-mentioned raw material compound may be added to react.
炭酸塩、炭酸水素塩の使用量はαアミノβハロ
ゲノニトリルの形態により異なるが、遊離形の場
合で代表して表わすと、炭酸塩の場合1.5〜10モ
ル倍、炭酸水素塩の場合2.0〜10モル倍、好まし
くは両者とも３〜６モル倍である。モル比が大き
すぎると副反応を惹起して好ましくない。 The amount of carbonate and hydrogen carbonate to be used varies depending on the form of α-amino-β halogenonitrile, but representatively in the case of free form, it is 1.5 to 10 times the mole for carbonate, and 2.0 to 10 times for hydrogen carbonate. The mole ratio is preferably 3 to 6 moles for both. If the molar ratio is too large, side reactions may occur, which is undesirable.
反応は通常水溶液中で実施されるが、低級アル
コール類、ジオキサン、テトラヒドロフラン等の
有機溶媒と水を混合した水性溶媒中でも実施され
る。 The reaction is usually carried out in an aqueous solution, but it can also be carried out in an aqueous solvent prepared by mixing water with an organic solvent such as a lower alcohol, dioxane or tetrahydrofuran.
反応温度は必ずしも制限はないが、一般に０〜
100℃、好ましくは30〜80℃の範囲であり、反応
時間は0.5〜30時間、通常1.0〜10時間の範囲であ
る。また、通常は常圧下に反応させるが必要によ
り加圧または減圧下に反応させてもよい。 The reaction temperature is not necessarily limited, but is generally between 0 and
The temperature is 100°C, preferably 30-80°C, and the reaction time is 0.5-30 hours, usually 1.0-10 hours. Further, although the reaction is usually carried out under normal pressure, the reaction may be carried out under increased pressure or reduced pressure if necessary.
以下、本発明の方法について代表的な例を示し
更に具体的に説明するが、これらは本発明につい
ての理解を容易にするための単なる例示であり、
本発明はこれらのみに限定されないことは勿論の
こと、これらによつて何ら制限されないことは言
うまでもない。 Hereinafter, typical examples of the method of the present invention will be shown and explained in more detail, but these are merely illustrative examples to facilitate understanding of the present invention.
It goes without saying that the present invention is not limited to these only, and is not limited in any way by these.
実施例 １
α−アミノ−β−クロロプロピオニトリル塩酸
塩2.12ｇを水50mlに溶解し、炭酸水素カリウム
4.46ｇを加え、50℃で１時間反応する。反応液を
高速液体クロマトグラフイーで分析したところα
−アミノβ−クロロプロピオニトリルの反応率92
％，２−オキソ−４−シアノオキサゾリンの収率
68％であつた。Example 1 2.12 g of α-amino-β-chloropropionitrile hydrochloride was dissolved in 50 ml of water, and potassium hydrogen carbonate was added.
Add 4.46g and react at 50°C for 1 hour. When the reaction solution was analyzed by high performance liquid chromatography, α
-Reaction rate of amino β-chloropropionitrile 92
%, yield of 2-oxo-4-cyanooxazoline
It was 68%.
実施例 ２
α−アミノ−β−クロロプロピオニトリル塩酸
塩3.53ｇと炭酸ナトリウム10.6ｇを水50mlに溶解
し、50℃，１時間反応する。反応後分析するとα
−アミノ−β−クロロプロピオニトリルの反応率
95％，２−オキソ−４−シアノオキサゾリジンの
収率62％であつた。Example 2 3.53 g of α-amino-β-chloropropionitrile hydrochloride and 10.6 g of sodium carbonate were dissolved in 50 ml of water and reacted at 50°C for 1 hour. When analyzed after reaction, α
-Amino-β-chloropropionitrile reaction rate
The yield of 2-oxo-4-cyanooxazolidine was 95% and 62%.
実施例 ３
α−アミノ−β−クロロプロピオニトリル塩酸
塩14.1ｇと炭酸水素ナトリウム33.6ｇを氷冷下、
水200mlに溶解し、30℃に昇温後、４時間反応す
る。反応後、分析すると、α−アミノ−β−クロ
ロプロピオニトリルの反応率は92％，２−オキソ
−４−シアノオキサゾリンの収率は73％であつ
た。Example 3 14.1 g of α-amino-β-chloropropionitrile hydrochloride and 33.6 g of sodium hydrogen carbonate were cooled on ice.
Dissolve in 200 ml of water, raise the temperature to 30°C, and react for 4 hours. After the reaction, analysis revealed that the reaction rate of α-amino-β-chloropropionitrile was 92% and the yield of 2-oxo-4-cyanooxazoline was 73%.
実施例 ４
α−アミノ−β−クロロブチニトリル塩酸塩
15.5ｇと炭酸水素アンモニウム48ｇを水100mlに
溶解し、50℃，1.5時間反応する。反応後分析す
ると２−オキソ−４−シアノ−５−メチルオキサ
ゾリジンの収率59％であつた。Example 4 α-amino-β-chlorobutinitrile hydrochloride
Dissolve 15.5 g and 48 g of ammonium hydrogen carbonate in 100 ml of water and react at 50°C for 1.5 hours. Analysis after the reaction revealed that the yield of 2-oxo-4-cyano-5-methyloxazolidine was 59%.
実施例 ５
炭酸水素アンモニウム32.0ｇを水200mlに溶か
し、氷冷しつつα−アミノ−β−クロロプロピオ
ニトリル（遊離形）10.5ｇをゆつくり加える。次
に30℃に昇温し、６時間反応する。Example 5 32.0 g of ammonium hydrogen carbonate is dissolved in 200 ml of water, and while cooling on ice, 10.5 g of α-amino-β-chloropropionitrile (free form) is slowly added. Next, the temperature was raised to 30°C and the reaction was carried out for 6 hours.
反応後分析すると２−オキソ−４−シアノオキ
サゾリジンの収率51％であつた。 Analysis after the reaction revealed that the yield of 2-oxo-4-cyanooxazolidine was 51%.
実施例 ６
炭酸カルシウム60ｇを水250mlに懸濁させ、二
酸化炭素を吹込んで沈殿を溶解させる。この溶液
にα−アミノ−β−ブロモプロピオニトリル塩酸
塩14.1ｇを加え50℃，2.5時間反応させる。反応
後分析すると２−オキソ−４−シアノオキサゾリ
ジンの収率47％であつた。Example 6 60 g of calcium carbonate is suspended in 250 ml of water and carbon dioxide is blown in to dissolve the precipitate. 14.1 g of α-amino-β-bromopropionitrile hydrochloride is added to this solution and reacted at 50°C for 2.5 hours. Analysis after the reaction revealed that the yield of 2-oxo-4-cyanooxazolidine was 47%.
Claims (1)
または低級アルキル基、Ｘはハロゲン原子を表わ
す。） にて表わされる化合物を水または水性溶媒中で、
アルカリ金属、アルカリ土類金属またはアンモニ
ウムの炭酸塩または炭酸水素塩と反応させること
を特徴とする、一般式 （式中、R1，R2およびR3は上記と同じ。） にて表わされる２−オキソ−４−シアノオキサゾ
リジン類の製造方法。[Claims] 1. General formula (In the formula, R 1 , R 2 and R 3 each represent a hydrogen atom or a lower alkyl group, and X represents a halogen atom.) In water or an aqueous solvent, a compound represented by
General formula, characterized by reaction with carbonates or bicarbonates of alkali metals, alkaline earth metals or ammonium (In the formula, R 1 , R 2 and R 3 are the same as above.) A method for producing 2-oxo-4-cyanooxazolidines represented by:
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP14247483A JPS6034954A (en) | 1983-08-05 | 1983-08-05 | Production of 2-oxo-4-cyanooxazolidines |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP14247483A JPS6034954A (en) | 1983-08-05 | 1983-08-05 | Production of 2-oxo-4-cyanooxazolidines |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6034954A JPS6034954A (en) | 1985-02-22 |
| JPH0449546B2 true JPH0449546B2 (en) | 1992-08-11 |
Family
ID=15316156
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP14247483A Granted JPS6034954A (en) | 1983-08-05 | 1983-08-05 | Production of 2-oxo-4-cyanooxazolidines |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6034954A (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP3728913B2 (en) * | 1998-02-06 | 2005-12-21 | 日本精工株式会社 | Vehicle steering device |
-
1983
- 1983-08-05 JP JP14247483A patent/JPS6034954A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6034954A (en) | 1985-02-22 |
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