FI77236C - Foerfarande foer framstaellning av bensimidazolderivat. - Google Patents
Foerfarande foer framstaellning av bensimidazolderivat. Download PDFInfo
- Publication number
- FI77236C FI77236C FI852139A FI852139A FI77236C FI 77236 C FI77236 C FI 77236C FI 852139 A FI852139 A FI 852139A FI 852139 A FI852139 A FI 852139A FI 77236 C FI77236 C FI 77236C
- Authority
- FI
- Finland
- Prior art keywords
- formula
- solution
- preparation
- rhodanide
- benzimidazole derivatives
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 12
- 238000002360 preparation method Methods 0.000 title claims description 6
- 229940058303 antinematodal benzimidazole derivative Drugs 0.000 title claims description 4
- 125000003785 benzimidazolyl group Chemical class N1=C(NC2=C1C=CC=C2)* 0.000 title claims 2
- 150000001875 compounds Chemical class 0.000 claims description 13
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 9
- ZMZDMBWJUHKJPS-UHFFFAOYSA-M Thiocyanate anion Chemical compound [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 claims description 5
- 229910052783 alkali metal Inorganic materials 0.000 claims description 3
- 150000001340 alkali metals Chemical group 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium group Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims description 2
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 14
- 239000000243 solution Substances 0.000 description 14
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000003960 organic solvent Substances 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-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
- 230000026030 halogenation Effects 0.000 description 3
- 238000005658 halogenation reaction Methods 0.000 description 3
- ZNNZYHKDIALBAK-UHFFFAOYSA-M potassium thiocyanate Chemical compound [K+].[S-]C#N ZNNZYHKDIALBAK-UHFFFAOYSA-M 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 229910021626 Tin(II) chloride Inorganic materials 0.000 description 2
- SOIFLUNRINLCBN-UHFFFAOYSA-N ammonium thiocyanate Chemical compound [NH4+].[S-]C#N SOIFLUNRINLCBN-UHFFFAOYSA-N 0.000 description 2
- 230000000507 anthelmentic effect Effects 0.000 description 2
- 150000001556 benzimidazoles Chemical class 0.000 description 2
- TWFZGCMQGLPBSX-UHFFFAOYSA-N carbendazim Chemical compound C1=CC=C2NC(NC(=O)OC)=NC2=C1 TWFZGCMQGLPBSX-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000001119 stannous chloride Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- TXUICONDJPYNPY-UHFFFAOYSA-N (1,10,13-trimethyl-3-oxo-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl) heptanoate Chemical compound C1CC2CC(=O)C=C(C)C2(C)C2C1C1CCC(OC(=O)CCCCCC)C1(C)CC2 TXUICONDJPYNPY-UHFFFAOYSA-N 0.000 description 1
- JVSORZTZKODIJB-UHFFFAOYSA-N (3,4-diaminophenyl) thiocyanate Chemical compound NC1=CC=C(SC#N)C=C1N JVSORZTZKODIJB-UHFFFAOYSA-N 0.000 description 1
- QUWHIBBGKKRYFW-UHFFFAOYSA-N (4-amino-3-nitrophenyl) thiocyanate Chemical compound NC1=CC=C(SC#N)C=C1[N+]([O-])=O QUWHIBBGKKRYFW-UHFFFAOYSA-N 0.000 description 1
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- SCVJRXQHFJXZFZ-KVQBGUIXSA-N 2-amino-9-[(2r,4s,5r)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-3h-purine-6-thione Chemical compound C1=2NC(N)=NC(=S)C=2N=CN1[C@H]1C[C@H](O)[C@@H](CO)O1 SCVJRXQHFJXZFZ-KVQBGUIXSA-N 0.000 description 1
- -1 2-substituted benzimidazoles Chemical class 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 1
- 239000000010 aprotic solvent Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 150000001913 cyanates Chemical class 0.000 description 1
- 238000004042 decolorization Methods 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000004675 formic acid derivatives Chemical class 0.000 description 1
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
- 125000006626 methoxycarbonylamino group Chemical group 0.000 description 1
- KHBXLYPOXVQKJG-UHFFFAOYSA-N methyl n-[(methoxycarbonylamino)-methylsulfanylmethylidene]carbamate Chemical compound COC(=O)NC(SC)=NC(=O)OC KHBXLYPOXVQKJG-UHFFFAOYSA-N 0.000 description 1
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- VGTPCRGMBIAPIM-UHFFFAOYSA-M sodium thiocyanate Chemical compound [Na+].[S-]C#N VGTPCRGMBIAPIM-UHFFFAOYSA-M 0.000 description 1
- 235000011150 stannous chloride Nutrition 0.000 description 1
Landscapes
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (10)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HUCI001975 | 1979-10-19 | ||
| HUCI001975 HU182763B (hu) | 1979-10-19 | 1979-10-19 | Eljárás 5(6)-alkiltio-benzimidazolil-alkil-karbamátok előállítására |
| HU63580 | 1980-03-19 | ||
| HU80635A HU182794B (en) | 1980-03-19 | 1980-03-19 | Process for producing 5-bracket-6-bracket closed-thiocyanato-benzimidazolyl-alkyl-carbamates and salts |
| HU197580 | 1980-04-22 | ||
| HU197580 | 1980-04-22 | ||
| HU138780 | 1980-06-03 | ||
| HU801387A HU184780B (en) | 1980-09-17 | 1980-09-17 | Process for producing thiocyanato-benzimidazoles |
| FI803278 | 1980-10-17 | ||
| FI803278A FI74277C (fi) | 1979-10-19 | 1980-10-17 | Foerfarande foer framstaellning av bensimidazolderivat. |
Publications (4)
| Publication Number | Publication Date |
|---|---|
| FI852139A0 FI852139A0 (en, 2012) | 1985-05-29 |
| FI852139L FI852139L (fi) | 1985-05-29 |
| FI77236B FI77236B (fi) | 1988-10-31 |
| FI77236C true FI77236C (fi) | 1989-02-10 |
Family
ID=27514601
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI852139A FI77236C (fi) | 1979-10-19 | 1985-05-29 | Foerfarande foer framstaellning av bensimidazolderivat. |
Country Status (1)
| Country | Link |
|---|---|
| FI (1) | FI77236C (en, 2012) |
-
1985
- 1985-05-29 FI FI852139A patent/FI77236C/fi not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| FI77236B (fi) | 1988-10-31 |
| FI852139A0 (en, 2012) | 1985-05-29 |
| FI852139L (fi) | 1985-05-29 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US6001831A (en) | Process for producing quinazoline derivatives | |
| US5099025A (en) | Preparation of 2-chloro-5-methyl-pyridine | |
| US6635765B2 (en) | Processes for preparing torsemide intermediate | |
| FI77236C (fi) | Foerfarande foer framstaellning av bensimidazolderivat. | |
| Nakayama et al. | General synthesis of dibenzotetrathiafulvalenes | |
| PL84503B1 (en, 2012) | ||
| WO2022206742A1 (zh) | 一种一步法合成乙内酰硫脲衍生物的方法 | |
| EP0135304A2 (en) | Preparation of substituted benzamides | |
| US5012015A (en) | Process for producing 2,4-dichloro-3-alkyl-6-nitrophenol | |
| GB1595029A (en) | Manufacture of 2,1,3-thiadiazin-4-one-2,2-dioxide derivatives | |
| KR950008208B1 (ko) | 메르캅토벤조에이트의 제조방법 | |
| CN112110871A (zh) | 一种3-异噻唑啉酮类化合物的制备方法 | |
| US3689502A (en) | Preparation of n-(2-alkylthioethyl) nitroimidazoles | |
| US4599428A (en) | Process for the preparation of 5(6)-thio substituted benzimidazoles | |
| US4473697A (en) | Production of thiocyanato benzimidazoles | |
| US5086000A (en) | Process for the preparation of alkylene-bis(2-pyridylamine) compounds and karl fischer reagents and methods utilizing such compounds | |
| US5453512A (en) | Method of producing 2-amino-3-nitro-5-halogenopyridine | |
| US4107179A (en) | Method for preparing ticrynafen | |
| US4691056A (en) | 3-halogenoacetonesulfonamides and a process for their preparation | |
| JP2002155058A (ja) | １位置換ヒダントイン類の製造方法 | |
| EP0080555B1 (de) | Verfahren zur Herstellung von 5(6)-Thiocyano-benzimidazol-Derivaten | |
| KR970006245B1 (ko) | N-벤조일-c-(1-메틸테트라졸-5-치오)이미도일 클로라이드 유도체 및 제조방법 | |
| JPH0140833B2 (en, 2012) | ||
| SK154294A3 (en) | Method of production of 2,4,5-tribrompyrole-3-carbonitrile | |
| JPH0678291B2 (ja) | シアノ置換エノ−ルエ−テルの製法 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM | Patent lapsed | ||
| MM | Patent lapsed |
Owner name: CHINOIN GYOGYSZER ES VEGYESZETI TERMEKEK GYARA RT. |