JPH0347173A - New method for preparing 1h-1,2,3-triazole - Google Patents
New method for preparing 1h-1,2,3-triazoleInfo
- Publication number
- JPH0347173A JPH0347173A JP1141638A JP14163889A JPH0347173A JP H0347173 A JPH0347173 A JP H0347173A JP 1141638 A JP1141638 A JP 1141638A JP 14163889 A JP14163889 A JP 14163889A JP H0347173 A JPH0347173 A JP H0347173A
- Authority
- JP
- Japan
- Prior art keywords
- triazole
- thiol
- thiobis
- metal
- subject substance
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 11
- QWENRTYMTSOGBR-UHFFFAOYSA-N 1H-1,2,3-Triazole Chemical compound C=1C=NNN=1 QWENRTYMTSOGBR-UHFFFAOYSA-N 0.000 title claims description 7
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 claims abstract description 10
- -1 amine salt Chemical class 0.000 claims abstract description 7
- 229910052751 metal Inorganic materials 0.000 claims abstract description 7
- 239000002184 metal Substances 0.000 claims abstract description 7
- LLCOQBODWBFTDD-UHFFFAOYSA-N 1h-triazol-1-ium-4-thiolate Chemical compound SC1=CNN=N1 LLCOQBODWBFTDD-UHFFFAOYSA-N 0.000 claims abstract description 5
- 150000003839 salts Chemical class 0.000 claims abstract description 5
- 150000002736 metal compounds Chemical class 0.000 claims abstract description 3
- 239000003054 catalyst Substances 0.000 claims abstract 3
- 239000007868 Raney catalyst Substances 0.000 claims description 9
- 229910000564 Raney nickel Inorganic materials 0.000 claims description 9
- 238000006722 reduction reaction Methods 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 6
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 3
- 229910017052 cobalt Inorganic materials 0.000 claims description 3
- 239000010941 cobalt Substances 0.000 claims description 3
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 3
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 claims description 3
- 230000000737 periodic effect Effects 0.000 claims description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract description 6
- 239000000203 mixture Substances 0.000 abstract description 5
- 239000002994 raw material Substances 0.000 abstract description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Substances C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 abstract description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 3
- 239000003814 drug Substances 0.000 abstract description 2
- 239000012280 lithium aluminium hydride Substances 0.000 abstract description 2
- 239000003960 organic solvent Substances 0.000 abstract description 2
- 239000000126 substance Substances 0.000 abstract 3
- ZTSUKZNLZYVSND-UHFFFAOYSA-N 4-(2h-triazol-4-ylsulfanyl)-2h-triazole Chemical compound C1=NNN=C1SC=1C=NNN=1 ZTSUKZNLZYVSND-UHFFFAOYSA-N 0.000 abstract 2
- 229940079593 drug Drugs 0.000 abstract 1
- 229910052987 metal hydride Inorganic materials 0.000 abstract 1
- 150000004681 metal hydrides Chemical class 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 19
- 238000003756 stirring Methods 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 229910052739 hydrogen Inorganic materials 0.000 description 6
- 239000001257 hydrogen Substances 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- XLBBOSZIFBBOPE-UHFFFAOYSA-N O.O.[Na].S=c1cn[nH][nH]1 Chemical compound O.O.[Na].S=c1cn[nH][nH]1 XLBBOSZIFBBOPE-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- SYOANZBNGDEJFH-UHFFFAOYSA-N 2,5-dihydro-1h-triazole Chemical compound C1NNN=C1 SYOANZBNGDEJFH-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- HHGMADGROXARPN-UHFFFAOYSA-M sodium;2h-triazole-4-thiolate Chemical compound [Na+].[S-]C=1C=NNN=1 HHGMADGROXARPN-UHFFFAOYSA-M 0.000 description 2
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- GTODOEDLCNTSLG-UHFFFAOYSA-N 2h-triazole-4-carboxylic acid Chemical compound OC(=O)C1=CNN=N1 GTODOEDLCNTSLG-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-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
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 230000000911 decarboxylating effect Effects 0.000 description 1
- 150000004683 dihydrates Chemical class 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- JUINSXZKUKVTMD-UHFFFAOYSA-N hydrogen azide Chemical compound N=[N+]=[N-] JUINSXZKUKVTMD-UHFFFAOYSA-N 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 229910003002 lithium salt Inorganic materials 0.000 description 1
- 159000000002 lithium salts Chemical class 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 150000004682 monohydrates Chemical class 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 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
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
Abstract
Description
【発明の詳細な説明】
〔産業上の利用分野〕
本発明は、医薬品等の原料化合物として有用な１Ｈ−１
，２，３−トリアゾールの新規な製法に関する。[Detailed Description of the Invention] [Industrial Application Field] The present invention provides 1H-1 useful as a raw material compound for pharmaceuticals, etc.
, 2,3-triazole.
１Ｈ−１，２，３−）リアゾールの製造方法としては、
八ｎｎ、ｃｈｉＩ１１． （Ｒｏｍｅ）、５Ｂ（１２）
、１５０７（１９６８）中に記載されているアセチレン
とアジ化水素酸の環状付加反応およびＡｎｎ、Ｃｈｅｍ
、 、 ２６２，３０２（１８９１）に記載されている
１Ｈ−１，２，３−トリアゾール−４−カルボン酸の脱
炭酸方法が知られている。The method for producing 1H-1,2,3-) riazole is as follows:
8nn, chiI11. (Rome), 5B (12)
, 1507 (1968) and Ann, Chem.
A method for decarboxylating 1H-1,2,3-triazole-4-carboxylic acid is known, as described in , 262, 302 (1891).
これら公知方法は、いずれも工業的な製造法としては適
していない、すなわち、前者の方法で用いるアジ化水素
酸は、毒性および爆発性の面で取り扱い上問題があり、
反応もオートクレーブ中、−５０℃で操作する必要があ
る。また、後者の方法は、原料の製造に同様の困難を伴
う、したがって、本発明は、ＬＨ−１，２，３−１−リ
アゾールについて上記した欠点のない、容易かつ、大量
合成に適した新規な製法を提供することを目的としてい
る。None of these known methods are suitable for industrial production; in other words, the hydrazoic acid used in the former method has problems in handling due to toxicity and explosiveness;
The reaction also needs to be operated at -50°C in an autoclave. The latter method also involves similar difficulties in the production of the raw materials, and therefore the present invention provides a novel method that is easy and suitable for large-scale synthesis without the drawbacks mentioned above for LH-1,2,3-1-lyazole. The aim is to provide a manufacturing method.
上記課題を解決するため、鋭意検討を行なった結果、工
業的に実施できる方法を確立し、本発明を完成するに至
った。In order to solve the above problems, as a result of intensive studies, an industrially applicable method was established and the present invention was completed.
本発明は、１Ｈ−１，２，３−トリアゾール−５−チオ
ール、その金属塩もしくはアミン塩、または５．５°−
チオビス（１Ｈ−１，２，３−トリアゾール）を還元反
応に付すことを特徴とする１Ｈ−１，２，３−トリアゾ
ールの新規な製法に関する。The present invention relates to 1H-1,2,3-triazole-5-thiol, its metal salt or amine salt, or 5.5°-
The present invention relates to a novel method for producing 1H-1,2,3-triazole, which is characterized by subjecting thiobis(1H-1,2,3-triazole) to a reduction reaction.
還元反応としては、周期律表第■属に属する金属化合物
（好ましくは、ラネーニッケル、ラネーコバルト、鉄粉
、パラジウム−炭素など、特に好ましい化合物はラネー
ニッケル）を触媒として用いる方法、水素化リチウムア
ルミニウム、水素化ホウ素ナトリウム、シアン化水素化
ホウ素ナトリウムなどの金属水素錯化合物を用いる方法
などがあげられる。The reduction reaction can be carried out using a metal compound belonging to Group Ⅰ of the periodic table (preferably Raney nickel, Raney cobalt, iron powder, palladium-carbon, etc., particularly preferably Raney nickel), lithium aluminum hydride, hydrogen Examples include methods using metal hydrogen complex compounds such as sodium borohydride and sodium cyanoborohydride.
ラネーニッケル等を用いる還元反応は水または有機溶媒
（メタノール、エタノール、ジエチルエーテル、酢酸エ
チル等）あるいはそれらの混合溶媒中、水素ガス雰囲気
上常圧または加圧下に進行する。金属水素錯化合物を用
いる還元反応は、好ましくはジエチルエーテル、テトラ
ヒドロフラン中、室温から約２００℃で約１時間から数
時間以内に進行する。The reduction reaction using Raney nickel or the like proceeds in water, an organic solvent (methanol, ethanol, diethyl ether, ethyl acetate, etc.), or a mixed solvent thereof, in a hydrogen gas atmosphere, at normal pressure or under increased pressure. The reduction reaction using the metal hydrogen complex preferably proceeds in diethyl ether, tetrahydrofuran at room temperature to about 200° C. within about 1 to several hours.
原料である１Ｈ−１，２，３−トリアゾール−５−チオ
ールは容易に入手可能であり、金属塩としてはナトリウ
ム、カリウム、カルシウム、リチウムなどの塩、アミン
塩としてはアンモニウム塩があげられ、また、水和物（
１水和物、２水和物など）も含まれる。５，５° −チ
オビス（１Ｈ−１，２，３−）リアゾール）もこの化合
物から節単に合成される。The raw material 1H-1,2,3-triazole-5-thiol is easily available, and examples of metal salts include sodium, potassium, calcium, and lithium salts, and examples of amine salts include ammonium salts. , hydrate (
(monohydrate, dihydrate, etc.) are also included. 5,5°-thiobis(1H-1,2,3-)lyazole) is also easily synthesized from this compound.
本発明方法は、比較的短時間に進行し、目的物が高収率
を得ることができ、操作も簡単かつ安全であり、既知の
製法に比べ容易にかつ安価で大量生産に通した製法であ
る。The method of the present invention proceeds in a relatively short time, can obtain a high yield of the target product, is simple and safe to operate, and can be easily and inexpensively mass-produced compared to known manufacturing methods. be.
次に、実施例をあげて本発明をさらに詳しく説明するが
、本発明はこれらに限定されるものではない。Next, the present invention will be explained in more detail with reference to Examples, but the present invention is not limited thereto.
実施例１
ラネーニッケル１６ｇをエタノール２５０−に懸濁し、
撹拌下１Ｈ−１，２，３−トリアゾール−５−チオール
ナトリウム塩・２水和物１６ｇを溶解し、オートクレ
ーブ中水素ガス圧１０に＋ｒ／ｄ下、１５０℃で４時間
加熱した。反応液を濾過後、濾液を濃縮し飽和食塩水に
溶解した。溶解液を１０％塩酸で中和し、酢酸エチルで
抽出後、減圧蒸留（沸点７７℃７６ｍｍＨｇ）を行ない
、１Ｈ−１，２，３−）リアゾール６．７ｇを得た。Example 1 16g of Raney nickel was suspended in 250ml of ethanol,
While stirring, 16 g of 1H-1,2,3-triazole-5-thiol sodium salt dihydrate was dissolved and heated at 150° C. for 4 hours under a hydrogen gas pressure of 10 +r/d in an autoclave. After filtering the reaction solution, the filtrate was concentrated and dissolved in saturated brine. The solution was neutralized with 10% hydrochloric acid, extracted with ethyl acetate, and then distilled under reduced pressure (boiling point: 77° C., 76 mmHg) to obtain 6.7 g of 1H-1,2,3-)riazole.
収率は９２．４％であった。The yield was 92.4%.
”Ｃ−ＮＭＲ，ＵＶ＋ ＩＲ，ＧＣ−Ｅｌ−Ｍａｓｓス
ペクトルデータは標品のものと一致した。``The C-NMR, UV+IR, and GC-El-Mass spectrum data matched those of the standard product.
実施例２
ラネーニッケル１６ｇをエタノール２５０−に懸濁し、
撹拌下１Ｈ−１，２，３−トリアゾール−５−チオール
ナトリウム塩・２水和物１６ｇを溶解し、オートクレ
ーブ中水素ガス圧１０ｋｇ／−下５０℃で７時間加熱し
た。実施例１と同様に処理して１Ｈ−１，２，３−トリ
アゾール５．２ｇを得た。収率は７５．２％であった。Example 2 16g of Raney nickel was suspended in 250ml of ethanol,
While stirring, 16 g of 1H-1,2,3-triazole-5-thiol sodium salt dihydrate was dissolved and heated at 50°C for 7 hours under a hydrogen gas pressure of 10 kg/- in an autoclave. It was treated in the same manner as in Example 1 to obtain 5.2 g of 1H-1,2,3-triazole. The yield was 75.2%.
実施例３
ラネーニッケル１６０ｇをエタノール５００ｉに懸濁し
、撹拌下１Ｈ−１．２．３−１−リアゾール−５−チオ
ール ナトリウム塩１６ｇを溶解し、２０℃で２０分間
反応した。実施例１と同様に処理して１Ｈ−１，２，３
−トリアゾール５．Ｏｇを得た。収率は８１．１％であ
った。Example 3 160 g of Raney nickel was suspended in 500 i of ethanol, 16 g of 1H-1.2.3-1-riazole-5-thiol sodium salt was dissolved under stirring, and the mixture was reacted at 20° C. for 20 minutes. 1H-1, 2, 3 was treated in the same manner as in Example 1.
-Triazole5. Obtained Og. The yield was 81.1%.
実施例４
ラネーニッケル１６ｇを水２５０−に懸濁し、撹拌下１
Ｈ−１，２，３−トリアゾール−５−チオール ナトリ
ウム塩・２水和物１６ｇを溶解し、実施例１と同様に処
理してＬＨ−１，２，３−）すアゾール６．２ｇを得た
。収率は９０．８％であった。Example 4 16g of Raney nickel was suspended in 250ml of water and mixed with stirring for 1 hour.
16 g of H-1,2,3-triazole-5-thiol sodium salt dihydrate was dissolved and treated in the same manner as in Example 1 to obtain 6.2 g of LH-1,2,3-)suazole. Ta. The yield was 90.8%.
実施例５
ラネーニッケル２０ｇをエタノール２５０ｄに懸濁し、
撹拌下５，５゛ −チオビス（１Ｈ−１゜２．３−１リ
アゾール）２０ｇを溶解し、実施例１と同様に処理して
ＬＨ−１，２，３−トリアゾール１２．８ ｇを得た。Example 5 20g of Raney nickel was suspended in 250d of ethanol,
While stirring, 20 g of 5,5゛-thiobis(1H-1゜2.3-1 riazole) was dissolved and treated in the same manner as in Example 1 to obtain 12.8 g of LH-1,2,3-triazole. .
収率は９２．６％であった。The yield was 92.6%.
実施例６
９０％酢酸１６０−にエタノール４０−と１Ｈ−１，２
，３−トリアゾール−５−チオール ナトリウム塩・２
水和物８ｇを室温で溶解し、これに鉄粉２ｇを加え、水
素の存在下４時間加熱還流した。実施例１と同様に処理
して１Ｈ−１，２゜３−トリアゾール２．２ｇを得た。Example 6 90% acetic acid 160-, ethanol 40- and 1H-1,2
,3-triazole-5-thiol sodium salt 2
8 g of hydrate was dissolved at room temperature, 2 g of iron powder was added thereto, and the mixture was heated under reflux for 4 hours in the presence of hydrogen. The mixture was treated in the same manner as in Example 1 to obtain 2.2 g of 1H-1,2°3-triazole.
収率は５７．９％であった。The yield was 57.9%.
実施例７
５０％パラジウム−炭素８０ｇをエタノール３２艷に懸
濁し、撹拌下１Ｈ−１，２，３−トリアゾール−５−チ
オール ナトリウム塩・２水和物８ｇを溶解後、水素の
存在下４時間加熱還流した。Example 7 80 g of 50% palladium-carbon was suspended in 32 bottles of ethanol, and 8 g of 1H-1,2,3-triazole-5-thiol sodium salt dihydrate was dissolved under stirring, followed by 4 hours in the presence of hydrogen. The mixture was heated to reflux.
実施例１と同様に処理して１Ｈ−１，２，３−トリアゾ
ール２．３ｇを得た。収率は６６．６％であった。It was treated in the same manner as in Example 1 to obtain 2.3 g of 1H-1,2,3-triazole. The yield was 66.6%.
実施例８
ラネーコバルト１６０ｇをエタノール５０（ｌｄに懸濁
し、撹拌下１Ｈ−１，２，３−トリアゾール−５−チオ
ール ナトリウム塩１６ｇを溶解し、水素の存在下２０
℃で２時間反応した。実施例１と同様に処理して１Ｈ−
１，２，３−１リアゾール４．９ｇを得た。収率は７０
．９％であった。Example 8 160 g of Raney cobalt was suspended in 50 (ld) ethanol, 16 g of 1H-1,2,3-triazole-5-thiol sodium salt was dissolved under stirring, and the solution was suspended in 20 g of ethanol in the presence of hydrogen.
The reaction was carried out at ℃ for 2 hours. 1H-
4.9 g of 1,2,3-1 riazole was obtained. Yield is 70
．． It was 9%.
Claims (3)
、その金属塩もしくはアミン塩、または５，５−チオビ
ス（１Ｈ−１，２，３−トリアゾール）を還元反応に付
すことを特徴とする１Ｈ−１，２，３−トリアゾールの
新規な製法。(1) 1H-1,2,3-triazole-5-thiol, its metal salt or amine salt, or 5,5-thiobis(1H-1,2,3-triazole) is subjected to a reduction reaction. A novel method for producing 1H-1,2,3-triazole.
て用いて還元反応を行なう請求項１記載の方法。(2) The method according to claim 1, wherein the reduction reaction is carried out using a metal compound belonging to Group VIII of the Periodic Table as a catalyst.
ウム−炭素から選ばれる触媒を用いて還元反応を行なう
請求項１記載の方法。(3) The method according to claim 1, wherein the reduction reaction is carried out using a catalyst selected from Raney nickel, Raney cobalt, iron powder, and palladium-carbon.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP9238289 | 1989-04-11 | ||
| JP1-92382 | 1989-04-11 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH0347173A true JPH0347173A (en) | 1991-02-28 |
Family
ID=14052874
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP1141638A Pending JPH0347173A (en) | 1989-04-11 | 1989-06-02 | New method for preparing 1h-1,2,3-triazole |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0347173A (en) |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS63230675A (en) * | 1987-03-19 | 1988-09-27 | Otsuka Chem Co Ltd | Production of 1,2,3-triazole and derivative thereof |
-
1989
- 1989-06-02 JP JP1141638A patent/JPH0347173A/en active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS63230675A (en) * | 1987-03-19 | 1988-09-27 | Otsuka Chem Co Ltd | Production of 1,2,3-triazole and derivative thereof |
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