JPH0477749B2 - - Google Patents
Info
- Publication number
- JPH0477749B2 JPH0477749B2 JP15854583A JP15854583A JPH0477749B2 JP H0477749 B2 JPH0477749 B2 JP H0477749B2 JP 15854583 A JP15854583 A JP 15854583A JP 15854583 A JP15854583 A JP 15854583A JP H0477749 B2 JPH0477749 B2 JP H0477749B2
- Authority
- JP
- Japan
- Prior art keywords
- alkali metal
- cyanoethylthiazolidine
- cyanoiminothiazolidine
- cyanoimino
- acrylonitrile
- 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
Links
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims description 3
- ARBBHFWFJNXAKC-UHFFFAOYSA-N [3-(2-cyanoethyl)-1,3-thiazolidin-2-ylidene]cyanamide Chemical compound N#CCCN1CCSC1=NC#N ARBBHFWFJNXAKC-UHFFFAOYSA-N 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- -1 alkali metal alkoxides Chemical class 0.000 description 1
- 229910000102 alkali metal hydride Inorganic materials 0.000 description 1
- 150000008046 alkali metal hydrides Chemical class 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 230000000507 anthelmentic effect Effects 0.000 description 1
- 229940124339 anthelmintic agent Drugs 0.000 description 1
- 239000000921 anthelmintic agent Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- FDPIMTJIUBPUKL-UHFFFAOYSA-N dimethylacetone Natural products CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000002464 receptor antagonist Substances 0.000 description 1
- 229940044551 receptor antagonist Drugs 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Thiazole And Isothizaole Compounds (AREA)
Description
【発明の詳細な説明】
本発明は、下式で示される２−（Ｎ−シアノイ
ミノ）−３−シアノエチルチアゾリジンの製造法
に関する。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a method for producing 2-(N-cyanoimino)-3-cyanoethylthiazolidine represented by the following formula.
化合物〔〕は、例えばH2レセプター拮抗剤
や駆虫剤などの合成原料として有用である。 Compound [] is useful as a raw material for synthesis of, for example, H 2 receptor antagonists and anthelmintics.
本発明方法によれば、式〔〕：
で示されるＮ−シアノイミノチアゾリジンと、ア
クリロニトリル（CH2＝CH−CN）とを溶媒中、
塩基の存在下に反応させることにより、目的化合
物〔〕が得られる。 According to the method of the present invention, the formula []: N-cyanoiminothiazolidine represented by and acrylonitrile (CH 2 =CH-CN) in a solvent,
By reacting in the presence of a base, the target compound [] can be obtained.
溶媒は、例えばアルコール、ジオキサン、ジメ
チルホルムアミド、ジメチルスルホキシド、アセ
トンなどが好適であり、塩基としてはアルカリ金
属水酸化物、アルカリ金属アルコキサイド、アル
カリ金属水素化物などの強塩基が適当である。反
応は、室温ないし50℃の加温下に効率よく進行す
る。 Suitable solvents include, for example, alcohol, dioxane, dimethylformamide, dimethyl sulfoxide, and acetone, and suitable bases include strong bases such as alkali metal hydroxides, alkali metal alkoxides, and alkali metal hydrides. The reaction proceeds efficiently under heating at room temperature to 50°C.
実施例
ｔ−ブタノール150mlにＮ−シアノイミノチア
ゾリジン12.7ｇ（0.1モル）を懸濁させ、これに
30％水酸化カリウム（KOH）のメタノール溶液
0.66mlを加え、40℃に加温する。一方、ｔ−ブタ
ノール10mlにアクリロニトリル10.9ｇ（0.206モ
ル）を溶かした溶液を準備し、これを上記反応液
に40分を要して滴下する。滴加終了後、その温度
のまま１時間攪拌する。反応液を留去し、残渣に
水を加えると、２−（Ｎ−シアノイミノ）−３−シ
アノエチルチアゾリジンの結晶を得る。このもの
は十分に純品である。収量14.2ｇ（78.8％）。融
点86℃。Example 12.7 g (0.1 mol) of N-cyanoiminothiazolidine was suspended in 150 ml of t-butanol, and
30% potassium hydroxide (KOH) in methanol
Add 0.66ml and warm to 40℃. On the other hand, a solution of 10.9 g (0.206 mol) of acrylonitrile dissolved in 10 ml of t-butanol is prepared, and this solution is added dropwise to the above reaction solution over a period of 40 minutes. After the dropwise addition is complete, the mixture is stirred at that temperature for 1 hour. The reaction solution is distilled off and water is added to the residue to obtain crystals of 2-(N-cyanoimino)-3-cyanoethylthiazolidine. This stuff is pure enough. Yield: 14.2g (78.8%). Melting point: 86℃.
IRνnax（Nujol）：2244，2183，1580，1450，
1365，1260，1065（cm-1）。 IRν nax (Nujol): 2244, 2183, 1580, 1450,
1365, 1260, 1065 (cm -1 ).
Claims (1)
トリルを、溶媒中、塩基の存在下に反応させるこ
とを特徴とする２−（Ｎ−シアノイミノ）−３−シ
アノエチルチアゾリジンの製造法。1. A method for producing 2-(N-cyanoimino)-3-cyanoethylthiazolidine, which comprises reacting N-cyanoiminothiazolidine and acrylonitrile in a solvent in the presence of a base.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP15854583A JPS6051186A (en) | 1983-08-30 | 1983-08-30 | Preparation of 2-(n-cyanoimino)-3-cyanoethylthiazolidine |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP15854583A JPS6051186A (en) | 1983-08-30 | 1983-08-30 | Preparation of 2-(n-cyanoimino)-3-cyanoethylthiazolidine |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6051186A JPS6051186A (en) | 1985-03-22 |
| JPH0477749B2 true JPH0477749B2 (en) | 1992-12-09 |
Family
ID=15674044
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP15854583A Granted JPS6051186A (en) | 1983-08-30 | 1983-08-30 | Preparation of 2-(n-cyanoimino)-3-cyanoethylthiazolidine |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6051186A (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS56174192U (en) * | 1980-05-27 | 1981-12-22 | ||
| JPS6224363Y2 (en) * | 1980-05-29 | 1987-06-22 | ||
| JP2597095B2 (en) * | 1987-06-09 | 1997-04-02 | 日本バイエルアグロケム株式会社 | Insecticides containing cyanoalkyl-heterocyclic compounds |
-
1983
- 1983-08-30 JP JP15854583A patent/JPS6051186A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6051186A (en) | 1985-03-22 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JPH0670056B2 (en) | Novel tetraoxo-diazabicyclo- (3,3,1) -nonane and process for producing the same | |
| JPH0477749B2 (en) | ||
| JPH0670049B2 (en) | Method for N-alkylation of dihydrolysergic acid | |
| JPS6212776A (en) | Rhodanine derivative | |
| JP2992334B2 (en) | Process for producing 2,4,5-tribromopyrrole-3-carbonitrile compound as molluscicide | |
| US3313850A (en) | Unsaturated acid amides containing sulphonic groups and method of preparation | |
| US3751462A (en) | Process for preparation of substituted fluoromethanesulfonanilides | |
| EP1035116B1 (en) | Process for the preparation of 1-[(cyclopent-3-en-1-yl)-methyl]-5-ethyl-6-(3,5-dimethylbenzoyl)-2,4-pyrimidinedione | |
| JP2604589B2 (en) | Method for producing imidazolidine derivative | |
| JPS5813551B2 (en) | Sinquinapiride (4,3-D) Pyrimidinedione | |
| JPS5939429B2 (en) | Method for producing benzylpyrimidine | |
| JPH033668B2 (en) | ||
| JP4123609B2 (en) | Process for producing 6- (α-fluoroalkyl) -4-pyrimidone | |
| JP3037399B2 (en) | Preparation of imidazole derivatives | |
| KR810000293B1 (en) | Process for preparing substituted amino quinazoline derivatives | |
| JPH0120150B2 (en) | ||
| JPS6051184A (en) | N-cyanoiminothiazolidine derivative and its preparation | |
| JPH0359065B2 (en) | ||
| JPS5813552B2 (en) | Sinquinapiride (4,3-D) Pyrimidinedione | |
| JPS60146852A (en) | Propanolamine derivative | |
| JPS6067451A (en) | 2-acetyl-2-amino-ethyl alcohol and production thereof | |
| JPH0873454A (en) | Method for producing cycloheptoimidazole derivative | |
| JPS58188860A (en) | Preparation of imidazole derivative | |
| JPS5838266A (en) | Improved manufacture of 2,4-diamino-5- (3',4',5'-trimethoxybenzyl)-pyrimidine | |
| JPS5813553B2 (en) | Sinquinapiride (4,3-D) Pyrimidinedione |