DE1795692A1 - Verfahren zur herstellung von 2(4'-thiazolyl)-benzimidazol - Google Patents
Verfahren zur herstellung von 2(4'-thiazolyl)-benzimidazolInfo
- Publication number
- DE1795692A1 DE1795692A1 DE19661795692 DE1795692A DE1795692A1 DE 1795692 A1 DE1795692 A1 DE 1795692A1 DE 19661795692 DE19661795692 DE 19661795692 DE 1795692 A DE1795692 A DE 1795692A DE 1795692 A1 DE1795692 A1 DE 1795692A1
- Authority
- DE
- Germany
- Prior art keywords
- benzimidazole
- thiazolyl
- chloro
- ecm
- preparation
- 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 6
- 238000002360 preparation method Methods 0.000 title claims description 4
- WJCNZQLZVWNLKY-UHFFFAOYSA-N thiabendazole Chemical compound S1C=NC(C=2NC3=CC=CC=C3N=2)=C1 WJCNZQLZVWNLKY-UHFFFAOYSA-N 0.000 title description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 5
- 229910052763 palladium Inorganic materials 0.000 claims description 2
- DDBREPKUVSBGFI-UHFFFAOYSA-N phenobarbital Chemical compound C=1C=CC=CC=1C1(CC)C(=O)NC(=O)NC1=O DDBREPKUVSBGFI-UHFFFAOYSA-N 0.000 claims description 2
- -1 1 -thiazolyl Chemical group 0.000 claims 1
- JYZIHLWOWKMNNX-UHFFFAOYSA-N benzimidazole Chemical compound C1=C[CH]C2=NC=NC2=C1 JYZIHLWOWKMNNX-UHFFFAOYSA-N 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 2
- UVYJJJQMZPCYKY-UHFFFAOYSA-N 2-chloro-1,3-thiazole-4-carboxylic acid Chemical compound OC(=O)C1=CSC(Cl)=N1 UVYJJJQMZPCYKY-UHFFFAOYSA-N 0.000 description 2
- DPJCXCZTLWNFOH-UHFFFAOYSA-N 2-nitroaniline Chemical compound NC1=CC=CC=C1[N+]([O-])=O DPJCXCZTLWNFOH-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 239000012452 mother liquor Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000006798 ring closing metathesis reaction Methods 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- QWEWLLNSJDTOKH-UHFFFAOYSA-N 1,3-thiazole-2-carboxamide Chemical compound NC(=O)C1=NC=CS1 QWEWLLNSJDTOKH-UHFFFAOYSA-N 0.000 description 1
- WRFKSVINLIQRKF-UHFFFAOYSA-N 1,3-thiazole-4-carbaldehyde Chemical compound O=CC1=CSC=N1 WRFKSVINLIQRKF-UHFFFAOYSA-N 0.000 description 1
- FTECMELMYALUQZ-UHFFFAOYSA-N 1,3-thiazole-4-carbonyl chloride Chemical compound ClC(=O)C1=CSC=N1 FTECMELMYALUQZ-UHFFFAOYSA-N 0.000 description 1
- HMVYYTRDXNKRBQ-UHFFFAOYSA-N 1,3-thiazole-4-carboxylic acid Chemical compound OC(=O)C1=CSC=N1 HMVYYTRDXNKRBQ-UHFFFAOYSA-N 0.000 description 1
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 1
- 208000006968 Helminthiasis Diseases 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 208000014837 parasitic helminthiasis infectious disease Diseases 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000011321 prophylaxis Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 238000011282 treatment Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- D—TEXTILES; PAPER
- D04—BRAIDING; LACE-MAKING; KNITTING; TRIMMINGS; NON-WOVEN FABRICS
- D04H—MAKING TEXTILE FABRICS, e.g. FROM FIBRES OR FILAMENTARY MATERIAL; FABRICS MADE BY SUCH PROCESSES OR APPARATUS, e.g. FELTS, NON-WOVEN FABRICS; COTTON-WOOL; WADDING ; NON-WOVEN FABRICS FROM STAPLE FIBRES, FILAMENTS OR YARNS, BONDED WITH AT LEAST ONE WEB-LIKE MATERIAL DURING THEIR CONSOLIDATION
- D04H13/00—Other non-woven fabrics
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HUCI000569 | 1965-09-08 | ||
| HUCI000568 | 1965-09-08 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1795692A1 true DE1795692A1 (de) | 1973-05-30 |
Family
ID=26318375
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19661795692 Pending DE1795692A1 (de) | 1965-09-08 | 1966-08-30 | Verfahren zur herstellung von 2(4'-thiazolyl)-benzimidazol |
| DE19661670379 Expired DE1670379C3 (de) | 1965-09-08 | 1966-08-30 | 2-(4'-Thiazolyl)-benzimidazole und deren Herstellung |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19661670379 Expired DE1670379C3 (de) | 1965-09-08 | 1966-08-30 | 2-(4'-Thiazolyl)-benzimidazole und deren Herstellung |
Country Status (9)
| Country | Link |
|---|---|
| AT (1) | AT275513B (enExample) |
| BE (1) | BE686641A (enExample) |
| CH (1) | CH491135A (enExample) |
| DE (2) | DE1795692A1 (enExample) |
| DK (2) | DK117496B (enExample) |
| FR (1) | FR8001M (enExample) |
| GB (2) | GB1153905A (enExample) |
| NL (1) | NL6612582A (enExample) |
| SE (1) | SE371643B (enExample) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AR034897A1 (es) * | 2001-08-07 | 2004-03-24 | Hoffmann La Roche | Derivados n-monoacilados de o-fenilendiaminas, sus analogos heterociclicos de seis miembros y su uso como agentes farmaceuticos |
-
1966
- 1966-08-30 DE DE19661795692 patent/DE1795692A1/de active Pending
- 1966-08-30 CH CH1252166A patent/CH491135A/de not_active IP Right Cessation
- 1966-08-30 DE DE19661670379 patent/DE1670379C3/de not_active Expired
- 1966-08-31 AT AT823666A patent/AT275513B/de active
- 1966-08-31 GB GB5149268A patent/GB1153905A/en not_active Expired
- 1966-08-31 GB GB38925/66A patent/GB1153904A/en not_active Expired
- 1966-09-07 NL NL6612582A patent/NL6612582A/xx unknown
- 1966-09-07 SE SE1205966A patent/SE371643B/xx unknown
- 1966-09-08 FR FR75769A patent/FR8001M/fr not_active Expired
- 1966-09-08 BE BE686641D patent/BE686641A/xx unknown
-
1968
- 1968-04-04 DK DK148868A patent/DK117496B/da unknown
-
1969
- 1969-09-15 DK DK492069A patent/DK118952B/da unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DK118952B (da) | 1970-10-26 |
| NL6612582A (enExample) | 1967-03-09 |
| CH491135A (de) | 1970-05-31 |
| DK117496B (da) | 1970-05-04 |
| DE1670379B2 (de) | 1975-01-30 |
| DE1670379A1 (de) | 1972-04-06 |
| GB1153904A (en) | 1969-06-04 |
| FR8001M (enExample) | 1970-07-27 |
| AT275513B (de) | 1969-10-27 |
| GB1153905A (en) | 1969-06-04 |
| BE686641A (enExample) | 1967-02-15 |
| SE371643B (enExample) | 1974-11-25 |
| DE1670379C3 (de) | 1975-10-02 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE1795769A1 (de) | Tetrahydrohomopyrimidazolderivate, deren saeureadditionssalze und quaternaeren salze sowie verfahren zu deren herstellung | |
| DE2419970A1 (de) | Tertiaere cyclische amine und verfahren zu ihrer herstellung | |
| DD220026A5 (de) | Verfahren zur herstellung von in 3-stellung amino-substituierten pyridazin-derivaten | |
| DE1795692A1 (de) | Verfahren zur herstellung von 2(4'-thiazolyl)-benzimidazol | |
| DE1129944B (de) | Verfahren zur Herstellung von Sebacin- oder 3-AEthylkorksaeure oder deren Gemischen | |
| DE2008692A1 (de) | Verfahren zur Herstellung von Indol-3carbonsäurederivaten und nach dem Verfahren erhältliche, neue Verbindungen | |
| DE69619267T2 (de) | Verfahren zur herstellung von 3-amino-1,2,4-benzotriazindioxide | |
| DE1235929B (de) | Verfahren zur Herstellung von 2-(2'-Pyrazinyl)-benzimidazol und seinen Salzen | |
| DE2111610C3 (de) | Verfahren zur Herstellung von Salzen von Pyrimidyl-pyridiniumderivaten | |
| DE3839329A1 (de) | Verfahren zur reduktiven enthalogenierung von aromaten | |
| CH502377A (de) | Verfahren zur Herstellung von 2-(4'-Thiazolyl)-benzimidazol | |
| DE2630946A1 (de) | 3-aminomethyl-4-homoisotwistan, dessen saeureadditionssalze und verfahren zur herstellung dieser verbindungen | |
| AT91239B (de) | Verfahren zur Darstellung von Kampfen aus Bornychlorid. | |
| AT304573B (de) | Verfahren zur Herstellung von neuen Purin-Verbindungen und von deren Salzen | |
| AT346848B (de) | Verfahren zur herstellung von 2,4-diamino-5-(2- methyl-4,5-dimethoxybenzyl)-pyrimidin | |
| AT286294B (de) | Verfahren zur herstellung von 2-(4'-thiazolyl)-benzimidazol | |
| AT241441B (de) | Verfahren zur Herstellung von N-(2,3-Dimethylphenyl)-anthranilsäure und deren Salzen | |
| DE2238761C3 (de) | Verfahren zur Herstellung 2substituierter 5-Benzothiazol-essigsäure-Verbindungen | |
| AT278037B (de) | Verfahren zur Herstellung neuer borhaltiger heterocyclischer Verbindungen | |
| AT366381B (de) | Verfahren zur herstellung von n-(3-(1'-3''oxapentamethylenamino-aethylidenamino)-2,4,6- | |
| DE904926C (de) | Verfahren zur Herstellung eines blauen Kuepenfarbstoffes | |
| DE1793467C (de) | Verfahren zur Herstellung von 4-Hydroxybenzonitrilen | |
| DE213713C (enExample) | ||
| DE1620334C (de) | Verfahren zur Reinigung von rohem 2,4,7-Triamino-6-phenylpteridin. Ausscheidung aus: 1217388 | |
| DE1921340C3 (de) | In 4-Stellung substituierte 2-Phenyl-5-haIogen-pyrimidine |