JPH0569827B2 - - Google Patents
Info
- Publication number
- JPH0569827B2 JPH0569827B2 JP1055837A JP5583789A JPH0569827B2 JP H0569827 B2 JPH0569827 B2 JP H0569827B2 JP 1055837 A JP1055837 A JP 1055837A JP 5583789 A JP5583789 A JP 5583789A JP H0569827 B2 JPH0569827 B2 JP H0569827B2
- Authority
- JP
- Japan
- Prior art keywords
- formula
- carboxylic acid
- esters
- group
- compound
- 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
Links
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 27
- -1 imidazole compound Chemical class 0.000 claims description 22
- 125000005907 alkyl ester group Chemical group 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 7
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 claims description 6
- IJJNTMLAAKKCML-UHFFFAOYSA-N tribenzyl borate Chemical compound C=1C=CC=CC=1COB(OCC=1C=CC=CC=1)OCC1=CC=CC=C1 IJJNTMLAAKKCML-UHFFFAOYSA-N 0.000 claims description 5
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
- 239000003513 alkali Substances 0.000 claims description 2
- 239000007795 chemical reaction product Substances 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 230000002194 synthesizing effect Effects 0.000 claims description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 5
- 229940073608 benzyl chloride Drugs 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 4
- 150000001735 carboxylic acids Chemical class 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 3
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- PQAMFDRRWURCFQ-UHFFFAOYSA-N 2-ethyl-1h-imidazole Chemical compound CCC1=NC=CN1 PQAMFDRRWURCFQ-UHFFFAOYSA-N 0.000 description 2
- LXBGSDVWAMZHDD-UHFFFAOYSA-N 2-methyl-1h-imidazole Chemical compound CC1=NC=CN1 LXBGSDVWAMZHDD-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- CYIDZMCFTVVTJO-UHFFFAOYSA-N pyromellitic acid Chemical compound OC(=O)C1=CC(C(O)=O)=C(C(O)=O)C=C1C(O)=O CYIDZMCFTVVTJO-UHFFFAOYSA-N 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- ARCGXLSVLAOJQL-UHFFFAOYSA-N trimellitic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 ARCGXLSVLAOJQL-UHFFFAOYSA-N 0.000 description 2
- BWYQCNUKLXIXOK-UHFFFAOYSA-M 1,3-dibenzylimidazol-1-ium;chloride Chemical compound [Cl-].C1=C[N+](CC=2C=CC=CC=2)=CN1CC1=CC=CC=C1 BWYQCNUKLXIXOK-UHFFFAOYSA-M 0.000 description 1
- 150000004963 1-benzylimidazoles Chemical class 0.000 description 1
- JDIIGWSSTNUWGK-UHFFFAOYSA-N 1h-imidazol-3-ium;chloride Chemical compound [Cl-].[NH2+]1C=CN=C1 JDIIGWSSTNUWGK-UHFFFAOYSA-N 0.000 description 1
- ZCUJYXPAKHMBAZ-UHFFFAOYSA-N 2-phenyl-1h-imidazole Chemical compound C1=CNC(C=2C=CC=CC=2)=N1 ZCUJYXPAKHMBAZ-UHFFFAOYSA-N 0.000 description 1
- FUOZJYASZOSONT-UHFFFAOYSA-N 2-propan-2-yl-1h-imidazole Chemical compound CC(C)C1=NC=CN1 FUOZJYASZOSONT-UHFFFAOYSA-N 0.000 description 1
- TYOXIFXYEIILLY-UHFFFAOYSA-N 5-methyl-2-phenyl-1h-imidazole Chemical compound N1C(C)=CN=C1C1=CC=CC=C1 TYOXIFXYEIILLY-UHFFFAOYSA-N 0.000 description 1
- ULKLGIFJWFIQFF-UHFFFAOYSA-N 5K8XI641G3 Chemical compound CCC1=NC=C(C)N1 ULKLGIFJWFIQFF-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 235000019445 benzyl alcohol Nutrition 0.000 description 1
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 1
- 239000004327 boric acid Substances 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 238000005185 salting out Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
Classifications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts
Landscapes
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Epoxy Resins (AREA)
Description
産業上の利用分野
本発明は１位未置換イミダゾール化合物をベン
ジル化して１−ベンジルイミダゾール化合物を合
成する方法に関するものであり、本発明の方法に
よつて得られる１−ベンジルイミダゾール化合物
はポリエポキシ樹脂の硬化剤及び硬化促進剤とし
て有用である。
従来の技術
１位未置換イミダゾール化合物と塩化ベンジル
とをHCI受容体（acceptor）の存在下、活性水素
をもたない適当な溶剤中で反応させる方法が知ら
れている。
発明が解決しようとする課題
１位未置換イミダゾール化合物に塩化ベンジル
を反応させてベンジル化する方法においては、次
のような問題点がある。即ち、１位未置換イミダ
ゾール化合物と塩化ベンジルの反応によつて生じ
た１−ベンジルイミダゾール化合物は、未反応の
塩化ベンジルと反応して１，３−ジベンジルイミ
ダゾリウム−クロライド化合物となり易いので、
不要なイミダゾリウム−クロライドが多量に副生
成し、また塩化ベンジルは催涙性を有するので取
扱いが困難であつた。
本発明方法はこのような難点を解消するために
為されるものである。
課題を解決するための手段
本発明者等はこのような事情に鑑み鋭意研究の
結果、１位未置換イミダゾール化合物とトリベン
ジル−ボレートをカルボン酸、カルボン酸無水
物、それらのベンジルエステルあるいはそれらの
低級アルキルエステルの共存下に加熱反応させ、
反応生成物をアルカリ中和することにより、１−
ベンジルイミダゾール化合物が効率よく得られる
ことを見い出し、本発明を導き出すことができ
た。
本発明の合成方法を反応式で示せば次の通りで
ある。
Industrial Application Field The present invention relates to a method for synthesizing a 1-benzylimidazole compound by benzylating an unsubstituted imidazole compound at the 1-position, and the 1-benzylimidazole compound obtained by the method of the present invention is a polyepoxy resin. It is useful as a curing agent and curing accelerator. Prior Art A method is known in which a 1-position unsubstituted imidazole compound and benzyl chloride are reacted in the presence of an HCI acceptor in a suitable solvent without active hydrogen. Problems to be Solved by the Invention In the method of benzylating a 1-position unsubstituted imidazole compound by reacting it with benzyl chloride, there are the following problems. That is, the 1-benzylimidazole compound produced by the reaction of the 1-position unsubstituted imidazole compound and benzyl chloride tends to react with unreacted benzyl chloride to form a 1,3-dibenzylimidazolium-chloride compound.
A large amount of unnecessary imidazolium chloride is produced as a by-product, and benzyl chloride has lachrymatory properties, making it difficult to handle. The method of the present invention is intended to overcome these difficulties. Means for Solving the Problems In view of the above circumstances, the present inventors have conducted intensive research and found that a 1-position unsubstituted imidazole compound and a tribenzyl-borate can be converted into carboxylic acids, carboxylic acid anhydrides, their benzyl esters, or their lower A heating reaction is carried out in the coexistence of an alkyl ester,
By neutralizing the reaction product with alkali, 1-
It was discovered that a benzylimidazole compound can be obtained efficiently, and the present invention was achieved. The reaction formula for the synthesis method of the present invention is as follows.
【化】[ka]
前記反応式において、カルボン酸、カルボン酸
無水物、それらのベンジルエステルあるいはそれ
らの低級アルキルエステルは、イミダゾール化合
物1.0モルに対して通常0.01ないし1.0モルの範囲
で使用されるが、特に好ましい範囲は0.05ないし
0.5モルである。またトリベンジル−ボレートは、
イミダゾール化合物1.0モルに対して通常0.33な
いし0.5モルの範囲で使用される。反応温度は200
ないし300℃の範囲であるが、特に230ないし260
℃の範囲が好適であり、この場合反応は６時間以
内で完結する。
本反応において、カルボン酸、カルボン酸無水
物、それらのベンジルエステルあるいはそれらの
低級アルキルエステルは触媒作用を示すが、これ
は一つの新しい知見と言える。
反応混合物に必要量の水酸化アルカリを加え、
ついで有機溶剤（例えばアセトン）を加え濾過を
行い、得られた瀘液の減圧蒸留を行うか、あるい
は反応混合物に過剰の水酸化アルカリと適当量の
水を加えて塩析し、油層の減圧蒸留を行うかのい
ずれにより、粗目的物１−ベンジルイミダゾール
化合物が得られる。
粗目的物に未反応のイミダゾール化合物に相当
するモル数の水酸化アルカリを加え、再び減圧蒸
留を行えば、未反応イミダゾール化合物を殆ど含
まない目的物が得られる。
本発明において使用されるカルボン酸、カルボ
ン酸無水物、それらのベンジルエステルおよび低
級アルキルエステルは、安息香酸、フタル酸、ト
リメリツト酸、ピロメリツト酸、イソフタル酸、
テレフタル酸、コハク酸、マレイン酸、アジピン
酸、それら酸無水物、それらのベンジルエステル
およびそれらの低級アルキルエステルである。
（ポリカルボン酸の場合はセミエステルも含む）
また、カルボン酸の各種低級アルキルエステ
ル、例えばメチルエステル、エチルエステル、プ
ロピルエステル、イソプロピルエステル及びブチ
ルエステル等を使用することができる。
トリベンジル−ボレート
In the above reaction formula, the carboxylic acid, carboxylic acid anhydride, benzyl ester thereof, or lower alkyl ester thereof is generally used in an amount of 0.01 to 1.0 mol per 1.0 mol of the imidazole compound, but a particularly preferable range is 0.05 mol. No
It is 0.5 mole. Tribenzyl borate is also
It is usually used in an amount of 0.33 to 0.5 mol per 1.0 mol of the imidazole compound. The reaction temperature is 200
In the range of 300℃ to 300℃, but especially 230 to 260℃
A range of 0.degree. C. is preferred, in which case the reaction is complete within 6 hours. In this reaction, carboxylic acids, carboxylic acid anhydrides, their benzyl esters, or their lower alkyl esters exhibit catalytic activity, which can be said to be a new finding. Add the required amount of alkali hydroxide to the reaction mixture,
Then, an organic solvent (for example, acetone) is added and filtered, and the resulting filtrate is distilled under reduced pressure, or an excess of alkali hydroxide and an appropriate amount of water are added to the reaction mixture for salting out, and the oil layer is distilled under reduced pressure. The crude target 1-benzylimidazole compound is obtained by either of these steps. By adding alkali hydroxide in the number of moles corresponding to the unreacted imidazole compound to the crude target product and performing vacuum distillation again, the target product containing almost no unreacted imidazole compound can be obtained. The carboxylic acids, carboxylic acid anhydrides, benzyl esters and lower alkyl esters thereof used in the present invention include benzoic acid, phthalic acid, trimellitic acid, pyromellitic acid, isophthalic acid,
Terephthalic acid, succinic acid, maleic acid, adipic acid, their acid anhydrides, their benzyl esters and their lower alkyl esters.
(In the case of polycarboxylic acids, semi-esters are also included.) Various lower alkyl esters of carboxylic acids, such as methyl esters, ethyl esters, propyl esters, isopropyl esters, butyl esters, etc. can also be used. Tribenzyl-borate
【式】
は、１モルのホウ酸H2CO3と３モル以上のベン
ジルアルコールを100℃以上で加熱し、生成水を
アゼオトロープ（azeotrope）〔b.p.98℃、水91wt
％〕の形で系外に除去したのち、残留物を減圧蒸
留して得られるb.p.3198〜205℃の無色の液体で
ある。
本発明において使用される代表的なイミダゾー
ル化合物は２−メチルイミダゾール（以下2MZ
で表わす）、２−エチルイミダゾール（以下2EZ
で表わす）、２−イソプロピルイミダゾール（以
下2IZで表わす）、２−フエニルイミダゾール（以
下2PZで表わす）、２−エチル−４−メチルイミ
ダゾール（以下2E4MZで表わす）及び２−フエ
ニル−４−メチルイミダゾール（以下2P4MZで
表わす）である。
本発明の方法によつて得られる各種の１−ベン
ジルイミダゾールの性質を表１に示す。
但し、TLCの展開はシリカＧとクロロホル
ム／メタノール、メタノールあるいはアセトンの
いずれかを用いて行つた。[Formula]: 1 mol of boric acid H 2 CO 3 and 3 mol or more of benzyl alcohol are heated at 100°C or higher, and the resulting water is converted into azeotrope [bp 98°C, water 91wt].
%] from the system, and the residue is distilled under reduced pressure. bp 3 It is a colorless liquid with a temperature of 198-205°C. A typical imidazole compound used in the present invention is 2-methylimidazole (hereinafter referred to as 2MZ
), 2-ethylimidazole (hereinafter referred to as 2EZ
), 2-isopropylimidazole (hereinafter referred to as 2IZ), 2-phenylimidazole (hereinafter referred to as 2PZ), 2-ethyl-4-methylimidazole (hereinafter referred to as 2E4MZ), and 2-phenyl-4-methylimidazole (hereinafter expressed as 2P4MZ). Table 1 shows the properties of various 1-benzylimidazoles obtained by the method of the present invention. However, TLC development was performed using Silica G and either chloroform/methanol, methanol, or acetone.
【表】
実施例 １〜16
１位未置換イミダゾール0.1モルと所定量のト
リベンジル−ボレート、所定量のカルボン酸、カ
ルボン酸無水物、カルボン酸ベンジルエステル、
あるいはカルボン酸低級アルキルエステルを混合
し、所定の条件で加熱反応させたのち、反応混合
物を所定の後処理したあと（あるいは後処理をせ
ずに）、減圧分留に付し、粗目的物の１−ベンジ
ルイミダゾール化合物を得た。
これらの試験条件及びその結果は表２に示した
とおりであつた。
得られた各粗目的物はTLC（シリカＧ）／アセ
トンで調べたところ、極く僅かの未反応イミダゾ
ールを含むのみであつた。[Table] Examples 1 to 16 0.1 mol of 1-position unsubstituted imidazole, predetermined amount of tribenzyl-borate, predetermined amount of carboxylic acid, carboxylic acid anhydride, carboxylic acid benzyl ester,
Alternatively, carboxylic acid lower alkyl esters are mixed and reacted by heating under predetermined conditions. After the reaction mixture is subjected to predetermined post-treatment (or without post-treatment), it is subjected to reduced pressure fractional distillation to obtain the crude target product. A 1-benzylimidazole compound was obtained. These test conditions and results were as shown in Table 2. When each crude target product obtained was examined by TLC (Silica G)/acetone, it was found that it contained only a very small amount of unreacted imidazole.
【表】【table】
Claims (1)
ル基またはフエニル基を表わし、R4は水素原子
またはメチル基を表わす。〕 で示される１位未置換イミダゾール化合物とトリ
ベンジル−ボレートをカルボン酸、カルボン酸無
水物、それらのベンジルエステルあるいはそれら
の低級アルキルエステルの共存下で加熱反応さ
せ、反応生成物をアルカリで中和することを特徴
とする 一般式 【式】 〔但し、R2とR4は前記のとおり。〕 で示される１−ベンジルイミダゾール化合物の合
成方法。[Claims] 1 General formula [Formula] [However, R 2 represents a methyl group, ethyl group, isopropyl group or phenyl group, and R 4 represents a hydrogen atom or a methyl group. ] A 1-position unsubstituted imidazole compound represented by the formula and tribenzyl-borate are heated and reacted in the presence of a carboxylic acid, a carboxylic acid anhydride, their benzyl ester or their lower alkyl ester, and the reaction product is neutralized with an alkali. A general formula [Formula] characterized by the following: [However, R 2 and R 4 are as described above. ] A method for synthesizing a 1-benzylimidazole compound shown in the following.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1055837A JPH02233662A (en) | 1989-03-07 | 1989-03-07 | Synthesis of 1-benzylimidazole compound |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1055837A JPH02233662A (en) | 1989-03-07 | 1989-03-07 | Synthesis of 1-benzylimidazole compound |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH02233662A JPH02233662A (en) | 1990-09-17 |
| JPH0569827B2 true JPH0569827B2 (en) | 1993-10-01 |
Family
ID=13010106
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP1055837A Granted JPH02233662A (en) | 1989-03-07 | 1989-03-07 | Synthesis of 1-benzylimidazole compound |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH02233662A (en) |
-
1989
- 1989-03-07 JP JP1055837A patent/JPH02233662A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPH02233662A (en) | 1990-09-17 |
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