JPS54144393A - Preparation of imidazo2,1-bthiazole derivative - Google Patents
Preparation of imidazo2,1-bthiazole derivativeInfo
- Publication number
- JPS54144393A JPS54144393A JP5265278A JP5265278A JPS54144393A JP S54144393 A JPS54144393 A JP S54144393A JP 5265278 A JP5265278 A JP 5265278A JP 5265278 A JP5265278 A JP 5265278A JP S54144393 A JPS54144393 A JP S54144393A
- Authority
- JP
- Japan
- Prior art keywords
- compound
- derivative
- halogen
- alkali
- reaction
- 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.)
- Granted
Links
- 150000001875 compounds Chemical class 0.000 abstract 5
- 229910052736 halogen Inorganic materials 0.000 abstract 5
- 150000002367 halogens Chemical class 0.000 abstract 4
- 239000003513 alkali Substances 0.000 abstract 3
- 238000006243 chemical reaction Methods 0.000 abstract 3
- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 abstract 2
- 239000003795 chemical substances by application Substances 0.000 abstract 2
- 230000005494 condensation Effects 0.000 abstract 2
- 238000009833 condensation Methods 0.000 abstract 2
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 abstract 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 abstract 2
- FKLJPTJMIBLJAV-UHFFFAOYSA-N Compound IV Chemical compound O1N=C(C)C=C1CCCCCCCOC1=CC=C(C=2OCCN=2)C=C1 FKLJPTJMIBLJAV-UHFFFAOYSA-N 0.000 abstract 1
- ZMZDMBWJUHKJPS-UHFFFAOYSA-M Thiocyanate anion Chemical compound [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 abstract 1
- 125000002252 acyl group Chemical group 0.000 abstract 1
- 229940124339 anthelmintic agent Drugs 0.000 abstract 1
- 239000000921 anthelmintic agent Substances 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 230000002140 halogenating effect Effects 0.000 abstract 1
- 230000026030 halogenation Effects 0.000 abstract 1
- 238000005658 halogenation reaction Methods 0.000 abstract 1
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 abstract 1
- 230000007062 hydrolysis Effects 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- 238000006798 ring closing metathesis reaction Methods 0.000 abstract 1
- 238000007363 ring formation reaction Methods 0.000 abstract 1
- 150000003585 thioureas Chemical class 0.000 abstract 1
Landscapes
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Abstract
PURPOSE: To prepare the title compound useful as an anthelmintic agent, in high yield, by halogenating an isothioureide derivative easily obtained from a novel thiourea derivative, and subjecting the product to the condensation ring-closure in the presence of an alkali in one step.
CONSTITUTION: The compound IV is prepared by the following steps: (1) reaction of a compound V with a thiocyanate in the presence of an acylating agent to afford a novel compound I (R is H, halogen, NO2; R' is acyl); (2) hydrolysis of the compound I with an alkali to afford the compound II; (3) reaction of the compound II with a compound of formula XCH2CH2Y (X is halogen; Y is OH, halogen) to give a compound III; (4) conversion of the compound III to a halogen derivative with a halogenation agent (pref. thionyl chloride), and (5) the condensation cyclization reaction of the halogen derivative in the presence of an alkali at 40W100°C.
COPYRIGHT: (C)1979,JPO&Japio
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP5265278A JPS54144393A (en) | 1978-05-04 | 1978-05-04 | Preparation of imidazo2,1-bthiazole derivative |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP5265278A JPS54144393A (en) | 1978-05-04 | 1978-05-04 | Preparation of imidazo2,1-bthiazole derivative |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS54144393A true JPS54144393A (en) | 1979-11-10 |
| JPS5527066B2 JPS5527066B2 (en) | 1980-07-17 |
Family
ID=12920779
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP5265278A Granted JPS54144393A (en) | 1978-05-04 | 1978-05-04 | Preparation of imidazo2,1-bthiazole derivative |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS54144393A (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS57187019U (en) * | 1981-05-23 | 1982-11-27 |
-
1978
- 1978-05-04 JP JP5265278A patent/JPS54144393A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5527066B2 (en) | 1980-07-17 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JPS54119494A (en) | Preparation of cephalosporin compound | |
| JPS54144393A (en) | Preparation of imidazo2,1-bthiazole derivative | |
| JPS5547651A (en) | Production of sulfoxyimine | |
| JPS5718641A (en) | Preparation of quinone | |
| JPS5711981A (en) | Theobromine derivative and its preparation | |
| JPS57144252A (en) | Preparation of aminoalkylthiol | |
| JPS57134448A (en) | Production of diaralkylamine | |
| JPS55111468A (en) | Preparation of n-benzyl-tetrahydro isoquinoline derivative | |
| JPS5576871A (en) | Chromanyloxy fatty acid homolog | |
| JPS5262234A (en) | Process for preparation of n_3'-hydroxyphenyl-2-methylbenzamide | |
| JPS54122257A (en) | Silicon-containing vinylphenol derivative and its preparation | |
| JPS5697271A (en) | Preparation of dihalogeno-5-trifluoromethylpyridine | |
| JPS5781454A (en) | Preparation of cysteamine mineral acid salt | |
| JPS5668668A (en) | Preparation of 2-indolinones | |
| JPS57197279A (en) | Novel hexaminum compound and its preparation | |
| JPS5629526A (en) | Preparation of acylcyanide | |
| JPS5750960A (en) | Preparation of novel 4- 1-oxo-2-isoindolinyl acetophenone | |
| JPS5734002A (en) | Preparation of sulfur tetrafluoride | |
| JPS55143962A (en) | Novel aldehyde compound and its preparation | |
| JPS53135998A (en) | Preparation of 6 alpha-acylaminopenicillanic acid 1-oxide | |
| JPS54106490A (en) | Propargylglycine derivative and its preparation | |
| JPS5581882A (en) | Preparation of hexahydronaphtho(1,2':4,5)imidazo(2,1-b)thiazole derivative | |
| JPS5564575A (en) | Preparation of 3-acyl-5-fluorouracil | |
| JPS55127366A (en) | Preparation of 4-(3-isopropylamino-2-hydroxypropoxy)-indole | |
| JPS57151655A (en) | Preparation of quinacridone compound |