JPH08239367A - Production of 2-amino-4,6-dichloropyrimidine - Google Patents
Production of 2-amino-4,6-dichloropyrimidineInfo
- Publication number
- JPH08239367A JPH08239367A JP34249795A JP34249795A JPH08239367A JP H08239367 A JPH08239367 A JP H08239367A JP 34249795 A JP34249795 A JP 34249795A JP 34249795 A JP34249795 A JP 34249795A JP H08239367 A JPH08239367 A JP H08239367A
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- JP
- Japan
- Prior art keywords
- phosphorus oxychloride
- mol
- reaction
- adcp
- amino
- 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.)
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
【発明の属する技術分野】本発明は、２−アミノ−４，
６−ジクロロピリミジン（ＡＤＣＰ）の製造法に関す
る。ＡＤＣＰをメトキシ化して生成する２−アミノ−
４，６−ジメトキシピリミジン（ＡＤＭＰ）は、特開昭
５９−１２２４８８号公報、特開昭６１−２１００８４
号公報及び特開昭６０−２０８９７７号公報に示される
ようなスルホニルウレア系除草剤の重要な中間体であ
る。TECHNICAL FIELD The present invention relates to 2-amino-4,
It relates to a method for producing 6-dichloropyrimidine (ADCP). 2-Amino-formed by methoxylation of ADCP
4,6-dimethoxypyrimidine (ADMP) is described in JP-A-59-122488 and JP-A-61-210084.
It is an important intermediate for sulfonylurea herbicides as disclosed in JP-A No. 60-208977.
【従来の技術及び課題】ＡＤＣＰは２−アミノ−４，６
−ジヒドロキシピリミジン（ＡＤＨＰ）をオキシ塩化リ
ン中で有機塩基を用いて製造している。ジャーナル・オ
ブ・ケミカル・ソサイティ（Ｊ．Ａｍ．Ｃｈｅｍ．Ｓｏ
ｃ．），第７３巻，３０１１頁（１９５１年）には触媒
量の有機塩基を用いて１０７℃の還流下反応することに
よってＡＤＣＰが収率８０％で得られたと記載されてい
る。しかし、次式に示される二量体の副生が多いため、
実際の収率は低く、特開昭６４−８３０７１号公報の追
試では収率４５．６％に過ぎない。2. Description of the Related Art ADCP is 2-amino-4,6
-Dihydroxypyrimidine (ADHP) is prepared with an organic base in phosphorus oxychloride. Journal of Chemical Society (J. Am. Chem. So
c. ), Vol. 73, p. 3011 (1951), it is described that ADCP was obtained in a yield of 80% by reacting with a catalytic amount of an organic base under reflux at 107 ° C. However, since there are many by-products of the dimer represented by the following formula,
The actual yield is low, and in the additional test of JP-A-64-83071, the yield is only 45.6%.
【化１】 一方、米国特許第３９９１１９０号では３倍モルの塩基
を用い１０７℃還流で反応して７０％の収率でＡＤＣＰ
が得られたと記載されている。追試の結果、主な副生成
物は二量体であった（比較例参照）。特開昭６４−８３
０７１号公報及び特開平１−３０８２６３号公報ではオ
キシ塩化リンだけでなく有機溶媒を用いて、塩基を加え
て収率良くＡＤＣＰを得ているが、容積効率が悪い上、
溶媒回収が煩雑である。また、上記の方法は何れも次式
に示されるＡＤＣＰのアミドが副生するので、同アミド
を分解してＡＤＣＰを回収する操作が必要である。Embedded image On the other hand, in US Pat. No. 3,991,190, a 3-fold molar amount of a base was used and the reaction was carried out at 107 ° C. under reflux to obtain ADCP in 70% yield.
Is obtained. As a result of the additional test, the main by-product was a dimer (see Comparative Example). JP-A 64-83
In JP071 and JP-A-1-308263, ADCP is obtained in good yield by adding a base using not only phosphorus oxychloride but also an organic solvent, but the volume efficiency is poor and
Solvent recovery is complicated. Further, in any of the above methods, an amide of ADCP represented by the following formula is produced as a by-product, and therefore an operation of decomposing the amide to recover ADCP is required.
【化２】 Embedded image
【課題を解決するための手段】本発明者等は上記反応の
欠点を克服すべく鋭意検討した結果、クロル化の収率の
低下は二量化反応が原因であり、その生成量は、クロル
化温度に大きく依存することが判明した。すなわち、本
発明者等は、２−アミノ−４，６−ジヒドロキシピリミ
ジン（ＡＤＨＰ）をオキシ塩化リン中で有機塩基を用い
て反応させ２−アミノ−４，６−ジクロロピリミジン
（ＡＤＣＰ）を製造する方法において、オキシ塩化リン
を６〜１００倍モル、好ましくは６〜２０倍モル用い、
反応温度を２０〜８０℃、好ましくは４０〜８０℃で行
うことを特徴とする方法（以下、本発明の方法という）
を見出し、本発明を完成した。Means for Solving the Problems As a result of intensive studies made by the present inventors to overcome the drawbacks of the above reaction, the decrease in the yield of chlorination is caused by the dimerization reaction, and the amount produced is chlorinated. It turned out to be highly dependent on temperature. That is, the present inventors produce 2-amino-4,6-dichloropyrimidine (ADCP) by reacting 2-amino-4,6-dihydroxypyrimidine (ADHP) with an organic base in phosphorus oxychloride. In the method, phosphorus oxychloride is used in an amount of 6 to 100 times, preferably 6 to 20 times,
A method characterized in that the reaction temperature is 20 to 80 ° C., preferably 40 to 80 ° C. (hereinafter referred to as the method of the present invention)
And completed the present invention.
【発明の実施の形態】本発明の方法は、ＡＤＨＰとオキ
シ塩化リンの混合物を無溶媒で２０〜８０℃とし、好ま
しくは４０〜８０℃とし、有機塩基を滴下する方法で実
行される。適温では二量体だけでなく、ＡＤＣＰのアミ
ドの生成量も非常に少なくなる。オキシ塩化リンの量
は、反応の進行と共に塩類の析出によって攪拌が困難と
なり、また反応温度が低い程スラリー状態が悪くなるの
で、一方、使用量が多いと回収が問題となるので、ＡＤ
ＨＰの６〜１００部、好ましくは６〜２０部である。塩
基は水を生成しない有機塩基を用いる。例えば、Ｎ−ジ
アルキルアニリン、ピリジン、トリアルキルアミン、置
換ピリジン等があげられ、回収が容易な水に難溶性の塩
基、例えば、Ｎ−ジアルキルアニリン、置換ピリジンが
好ましい。塩基の量はＡＤＨＰ１モルに対して１．５〜
３モル、好ましくは２．０〜２．４モルである。反応温
度は、反応に対して非常に影響が大きく、高温では副生
成物の二量体が多くなり、低温では反応速度が遅く時間
を要するので、２０℃〜８０℃、好ましくは４０〜８０
℃である。反応時間は、反応温度、使用するオキシ塩化
リンの量、及び塩基の種類と量に依存し、特に反応温度
が大きな要因となるが、０．５〜７２時間、好ましくは
１〜１２時間である。反応後、未反応のオキシ塩化リン
を８０℃以下で減圧留去する。得られた固体に１〜１０
０部の水を徐々に加えて塩類を溶解し、過剰のオキシ塩
化リン類を加水分解すると目的物が固体として析出す
る。この際、ＡＤＣＰは高温下では水と反応して２−ア
ミノ−４−クロル−６−ヒドロキシピリミジンを生成す
るので、６０℃以下で操作するのが好ましい。反応終了
後、操作性の改善のためにクロロベンゼンまたはジクロ
ロベンゼンを加えてオキシ塩化リンを減圧下で留去し、
その後、加水分解してもよい。加水分解の方法は先に記
載の溶媒無添加時と同様である。析出した固体は濾取し
た後、水洗して酸分を除去し、乾燥して次工程に使用す
る。 〔参考〕ＡＤＣＰよりＡＤＭＰの製造方法 本発明の方法で得られるＡＤＣＰは通常ナトリウムメト
キシド等でジメトキシ化することにより、ＡＤＭＰをほ
ぼ定量的に製造できる。また、水酸化アルカリ−メタノ
ールでもメトキシ化できる（特開昭６４−１６７７０号
公報）。なお、水酸化アルカリとメタノールを使用する
場合は乾燥したＡＤＣＰを使用する必要がない。このと
き、水酸化アルカリとしては水酸化ナトリウム、水酸化
カリウム、水酸化バリウム、水酸化カルシウム等が使用
できるが、水酸化ナトリウムが経済性、反応性から好ま
しい。水酸化アルカリの使用量はＡＤＣＰの２〜３等量
である。常圧還流下では、２．５〜３等量必要である
が、オートクレーブを使用し、高温下、例えば１２０℃
で反応させれば、ほぼ理論量（２等量）で行うことがで
きる。水酸化アルカリとメタノールで使用する場合は数
％の２−アミノ−４−ヒドロキシ−６−メトキシピリミ
ジンの生成が認められるが、アルカリ塩として水洗によ
って容易に除去できる。BEST MODE FOR CARRYING OUT THE INVENTION The method of the present invention is carried out by a method in which a mixture of ADHP and phosphorus oxychloride is kept at 20 to 80 ° C., preferably 40 to 80 ° C. without a solvent, and an organic base is added dropwise. At an appropriate temperature, not only the dimer but also the amount of ADCP amide produced is significantly reduced. The amount of phosphorus oxychloride becomes difficult to stir due to the precipitation of salts as the reaction progresses, and the lower the reaction temperature, the worse the slurry state. On the other hand, if the amount used is large, recovery becomes a problem.
HP is 6 to 100 parts, preferably 6 to 20 parts. As the base, an organic base that does not generate water is used. Examples thereof include N-dialkylaniline, pyridine, trialkylamine, and substituted pyridine. Preference is given to a water-insoluble base that is easily recovered, such as N-dialkylaniline and substituted pyridine. The amount of base is 1.5 to 1 mol of ADHP.
It is 3 mol, preferably 2.0 to 2.4 mol. The reaction temperature has a great influence on the reaction, and a dimer of a by-product is increased at a high temperature, and a reaction rate is slow and takes a long time at a low temperature.
° C. The reaction time depends on the reaction temperature, the amount of phosphorus oxychloride used, and the type and amount of the base, and the reaction temperature is a major factor, but is 0.5 to 72 hours, preferably 1 to 12 hours. . After the reaction, unreacted phosphorus oxychloride is distilled off under reduced pressure at 80 ° C or lower. 1-10 for the obtained solid
When 0 part of water is gradually added to dissolve salts and the excess phosphorus oxychloride is hydrolyzed, the target substance is precipitated as a solid. At this time, ADCP reacts with water at high temperature to form 2-amino-4-chloro-6-hydroxypyrimidine, and therefore it is preferable to operate at 60 ° C. or lower. After completion of the reaction, chlorobenzene or dichlorobenzene was added to improve operability, and phosphorus oxychloride was distilled off under reduced pressure.
Then, you may hydrolyze. The method of hydrolysis is the same as that when no solvent is added as described above. The precipitated solid is collected by filtration, washed with water to remove the acid content, dried and used in the next step. [Reference] Method for Producing ADMP from ADCP ADCP obtained by the method of the present invention can be generally quantitatively produced by subjecting ADCP to dimethoxylation such as sodium methoxide. Further, it can be methoxylated with alkali hydroxide-methanol (JP-A-64-16770). When using alkali hydroxide and methanol, it is not necessary to use dry ADCP. At this time, sodium hydroxide, potassium hydroxide, barium hydroxide, calcium hydroxide or the like can be used as the alkali hydroxide, but sodium hydroxide is preferable from the viewpoint of economy and reactivity. The amount of alkali hydroxide used is 2 to 3 equivalents of ADCP. Under normal pressure reflux, 2.5 to 3 equivalents are required, but using an autoclave, at high temperature, for example 120 ° C.
If the reaction is carried out in step 1, it can be carried out in a theoretical amount (2 equivalents). When used with alkali hydroxide and methanol, a few% of 2-amino-4-hydroxy-6-methoxypyrimidine is observed to be produced, but it can be easily removed by washing with water as an alkali salt.
〔実施例１〕オキシ塩化リン１４４．８ｇ（０．９４２
モル）に、ＡＤＨＰ２０．０ｇ（０．１５７モル）加え
て、６０℃に昇温した。その後、攪拌しながら５−エチ
ル−２−ピコリン４５．８ｇ（０．３１４モル）を１時
間かけて滴下した。反応を更に２．５時間続けた。その
後、１，２−ジクロロベンゼン９４ｇを加え、オキシ塩
化リンを減圧留去した後、スラリー状反応液を５０℃、
３００ｍｌの水にあけ、析出した結晶を濾取し、２０ｍ
ｌの水で２回洗浄した。これを乾燥させることによりＡ
ＤＣＰ２３．３ｇを得た。収率９０％。 〔実施例２〕オキシ塩化リン２６．８ｇ（０．１７５モ
ル）に、ＡＤＨＰ３．２ｇ（０．０２５モル）加えて、
６０℃に昇温した。その後、攪拌しながらＮ，Ｎ−ジメ
チルアニリン７．３ｇ（０．０６０モル）を１時間かけ
て滴下した。反応を更に５時間続けた。その後、１，２
−ジクロロベンゼン１５ｇを加え、オキシ塩化リンを減
圧留去した後、スラリー状反応液を５０℃、５０ｍｌの
水にあけ、析出した結晶を濾取し、３ｍｌの水で２回洗
浄した。これを乾燥させることによりＡＤＣＰ３．４ｇ
を得た。収率８３％。 〔実施例３〕オキシ塩化リン２６．８ｇ（０．１７５モ
ル）に、ＡＤＨＰ３．２ｇ（０．０２５モル）加えて、
６０℃に昇温した。その後、攪拌しながらトリエチルア
ミン５．１ｇ（０．０５０モル）を４５分かけて滴下し
た。反応を更に５時間続けた。その後、１，２−ジクロ
ロベンゼン１５ｇを加え、オキシ塩化リンを減圧留去し
た後、スラリー状反応液を５０℃、５０ｍｌの水にあ
け、析出した結晶を濾取し、３ｍｌの水で２回洗浄し
た。これを乾燥させることによりＡＤＣＰ３．６ｇを得
た。収率８７％。 〔実施例４〕オキシ塩化リン２６．８ｇ（０．１７５モ
ル）に、ＡＤＨＰ３．２ｇ（０．０２５モル）加えて、
４０℃に昇温した。その後、攪拌しながら５−エチル−
２−ピコリン６．１ｇ（０．０５０モル）を１時間かけ
て滴下した。反応を更に１３．５時間続けた。その後、
１，２−ジクロロベンゼン１５ｇを加え、オキシ塩化リ
ンを減圧留去した後、スラリー状反応液を５０℃、５０
ｍｌの水にあけ、析出した結晶を濾取し、３ｍｌの水で
２回洗浄した。これを乾燥させることによりＡＤＣＰ
３．１ｇを得た。収率７５％。 〔実施例５〕オキシ塩化リン１４４．８ｇ（０．９４２
モル）に、ＡＤＨＰ２０．０ｇ（０．１５７モル）加え
て、６０℃に昇温した。その後、攪拌しながら５−エチ
ル−２−ピコリン４５．８ｇ（０．３１４モル）を１時
間かけて滴下した。反応を更に２．５時間続けた。その
後、オキシ塩化リンを減圧留去し、得られた粘性油状物
を５０℃、３００ｍｌの水にあけた。析出した結晶を濾
取し、２０ｍｌの水で２回洗浄した。これを乾燥させる
ことによりＡＤＣＰ２３．３ｇを得た。収率９０％。 〔比較例〕オキシ塩化リン２６．８ｇ（０．１７５モ
ル）に、ＡＤＨＰ３．２ｇ（０．０２５モル）加えて、
１００℃に昇温した。その後、攪拌しながら５−エチル
−２−ピコリン６．１ｇ（０．０５０モル）を１時間か
けて滴下した。反応を更に１時間続けた。その後、１，
２−ジクロロベンゼン１５ｇを加え、オキシ塩化リンを
減圧留去した後、スラリー状反応液を５０℃、５０ｍｌ
の水にあけ、析出した結晶を濾取し、３ｍｌの水で２回
洗浄した。これを乾燥させることによりＡＤＣＰ２．９
ｇを得た。収率７０％。液体クロマトグラフィー分析に
よると、主な副生成物は二量体であった。 〔参考例１〕オートクレープにメタノール１５ｍｌおよ
び水酸化ナトリウム１．６０ｇ（４０．０ｍｍｏｌ）を
仕込み溶解させた後、ＡＤＣＰ３．２８ｇ（２０．０ｍ
ｍｏｌ）を徐々に加え、１２０℃で３時間加熱した（内
圧：〜５ｋｇ／ｃｍ2 ）。冷却後、反応混合物からメタ
ノールを留去し、メチルイソブチルケトン２０ｇを加
え、水酸化ナトリウム水溶液で洗浄した後、水で洗浄し
た。有機層を芒硝で乾燥し、メチルイソブチルケトンを
留去してＡＤＭＰを２．８５ｇ得た。収率９３％。 〔参考例２〕水酸化ナトリウム２．４０ｇ（６０．０ｍ
ｍｏｌ）をメタノール８ｍｌに溶かし、ＡＤＣＰ３．２
８ｇ（２０．０ｍｍｏｌ）を徐々に加え、還流下に１時
間加熱した。冷却後、反応混合物からメタノールを留去
し、メチルイソブチルケトン２０ｇを加えて水で洗浄し
た。有機層を芒硝で乾燥し、溶媒を留去してＡＤＭＰを
２．７６ｇ得た。収率９０％。[Example 1] 144.8 g (0.942) of phosphorus oxychloride
20.0 g (0.157 mol) of ADHP was added to (mol) and the temperature was raised to 60 ° C. After that, while stirring, 45.8 g (0.314 mol) of 5-ethyl-2-picoline was added dropwise over 1 hour. The reaction was continued for another 2.5 hours. Thereafter, 94 g of 1,2-dichlorobenzene was added, phosphorus oxychloride was distilled off under reduced pressure, and the slurry reaction solution was heated to 50 ° C.
Pour into 300 ml of water and collect the precipitated crystals by filtration.
It was washed twice with 1 l of water. By drying this, A
23.3 g of DCP was obtained. Yield 90%. [Example 2] To 26.8 g (0.175 mol) of phosphorus oxychloride, 3.2 g (0.025 mol) of ADHP was added,
The temperature was raised to 60 ° C. Then, 7.3 g (0.060 mol) of N, N-dimethylaniline was added dropwise over 1 hour while stirring. The reaction was continued for another 5 hours. Then 1, 2
-15 g of dichlorobenzene was added, phosphorus oxychloride was distilled off under reduced pressure, the slurry reaction solution was poured into 50 ml of water at 50 ° C, and the precipitated crystals were collected by filtration and washed twice with 3 ml of water. By drying this, 3.4 g of ADCP
I got Yield 83%. [Example 3] To 26.8 g (0.175 mol) of phosphorus oxychloride, 3.2 g (0.025 mol) of ADHP was added,
The temperature was raised to 60 ° C. Then, while stirring, 5.1 g (0.050 mol) of triethylamine was added dropwise over 45 minutes. The reaction was continued for another 5 hours. Then, 15 g of 1,2-dichlorobenzene was added, phosphorus oxychloride was distilled off under reduced pressure, the slurry reaction solution was poured into 50 ml of water at 50 ° C., and the precipitated crystals were collected by filtration and twice with 3 ml of water. Washed. This was dried to obtain 3.6 g of ADCP. Yield 87%. [Example 4] To 26.8 g (0.175 mol) of phosphorus oxychloride, 3.2 g (0.025 mol) of ADHP was added,
The temperature was raised to 40 ° C. Then, while stirring, 5-ethyl-
6.1 g (0.050 mol) of 2-picoline was added dropwise over 1 hour. The reaction was continued for another 13.5 hours. afterwards,
After 15 g of 1,2-dichlorobenzene was added and phosphorus oxychloride was distilled off under reduced pressure, the slurry reaction solution was heated to 50 ° C. at 50 ° C.
The mixture was poured into ml of water, the precipitated crystals were collected by filtration, and washed twice with 3 ml of water. By drying this, ADCP
3.1 g was obtained. Yield 75%. [Example 5] 144.8 g of phosphorus oxychloride (0.942)
20.0 g (0.157 mol) of ADHP was added to (mol) and the temperature was raised to 60 ° C. After that, while stirring, 45.8 g (0.314 mol) of 5-ethyl-2-picoline was added dropwise over 1 hour. The reaction was continued for another 2.5 hours. Then, phosphorus oxychloride was distilled off under reduced pressure, and the resulting viscous oily substance was poured into 300 ml of water at 50 ° C. The precipitated crystals were collected by filtration and washed twice with 20 ml of water. By drying this, 23.3 g of ADCP was obtained. Yield 90%. [Comparative Example] To 26.8 g (0.175 mol) of phosphorus oxychloride, 3.2 g (0.025 mol) of ADHP was added,
The temperature was raised to 100 ° C. Then, 6.1 g (0.050 mol) of 5-ethyl-2-picoline was added dropwise over 1 hour while stirring. The reaction was continued for another hour. Then 1,
After 2-dichlorobenzene (15 g) was added and phosphorus oxychloride was distilled off under reduced pressure, the slurry reaction solution was heated to 50 ° C. and 50 ml.
Of water, the precipitated crystals were collected by filtration, and washed twice with 3 ml of water. By drying this, ADCP2.9
g was obtained. Yield 70%. The major by-product was a dimer by liquid chromatography analysis. [Reference Example 1] After 15 ml of methanol and 1.60 g (40.0 mmol) of sodium hydroxide were charged and dissolved in an autoclave, ADCP 3.28 g (20.0 m)
mol) was gradually added and the mixture was heated at 120 ° C. for 3 hours (internal pressure: ˜5 kg / cm 2 ). After cooling, methanol was distilled off from the reaction mixture, 20 g of methyl isobutyl ketone was added, and the mixture was washed with an aqueous sodium hydroxide solution and then with water. The organic layer was dried over sodium sulfate and the methyl isobutyl ketone was distilled off to obtain 2.85 g of ADMP. Yield 93%. [Reference Example 2] 2.40 g (60.0 m) of sodium hydroxide
mol) in 8 ml of methanol, and ADCP 3.2
8 g (20.0 mmol) was gradually added, and the mixture was heated under reflux for 1 hour. After cooling, methanol was distilled off from the reaction mixture, 20 g of methyl isobutyl ketone was added, and the mixture was washed with water. The organic layer was dried over sodium sulfate and the solvent was distilled off to obtain 2.76 g of ADMP. Yield 90%.
フロントページの続き (72)発明者 村上 博 千葉県船橋市坪井町722番地１日産化学工 業株式会社中央研究所内Front Page Continuation (72) Inventor Hiroshi Murakami 1 722 Tsuboi-cho, Funabashi City, Chiba 1 Nissan Chemical Industry Co., Ltd. Central Research Laboratory
Claims (4)
ミジンをオキシ塩化リン中で有機塩基を用いて反応させ
２−アミノ−４，６−ジクロロピリミジンを製造する方
法において、オキシ塩化リンを６〜１００倍モル用い、
反応温度を２０〜８０℃で行うことを特徴とする方法。1. A method for producing 2-amino-4,6-dichloropyrimidine by reacting 2-amino-4,6-dihydroxypyrimidine with an organic base in phosphorus oxychloride, wherein 6 to 6 phosphorus oxychloride is added. Use 100 times mole,
A method characterized in that the reaction temperature is 20 to 80 ° C.
請求項１の方法。2. The method according to claim 1, wherein the phosphorus oxychloride is used in a 6- to 20-fold molar quantity.
の方法。3. The reaction temperature is 40 to 80 ° C.
the method of.
反応温度を４０〜８０℃で行う請求項１の方法。4. A 6 to 20-fold molar amount of phosphorus oxychloride is used,
The method according to claim 1, wherein the reaction temperature is 40 to 80 ° C.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP34249795A JPH08239367A (en) | 1995-01-04 | 1995-12-28 | Production of 2-amino-4,6-dichloropyrimidine |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2995 | 1995-01-04 | ||
| JP7-29 | 1995-01-04 | ||
| JP34249795A JPH08239367A (en) | 1995-01-04 | 1995-12-28 | Production of 2-amino-4,6-dichloropyrimidine |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH08239367A true JPH08239367A (en) | 1996-09-17 |
Family
ID=26332939
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP34249795A Pending JPH08239367A (en) | 1995-01-04 | 1995-12-28 | Production of 2-amino-4,6-dichloropyrimidine |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH08239367A (en) |
-
1995
- 1995-12-28 JP JP34249795A patent/JPH08239367A/en active Pending
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