SU706023A3 - Способ получени производных -(1,3,4-тиадиазол-2ил) бензамида - Google Patents
Способ получени производных -(1,3,4-тиадиазол-2ил) бензамидаInfo
- Publication number
- SU706023A3 SU706023A3 SU772446348A SU2446348A SU706023A3 SU 706023 A3 SU706023 A3 SU 706023A3 SU 772446348 A SU772446348 A SU 772446348A SU 2446348 A SU2446348 A SU 2446348A SU 706023 A3 SU706023 A3 SU 706023A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- hydrogen
- phenyl
- bromine
- chlorophenyl
- chlorine
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 5
- RWOUBULBQYRRNL-UHFFFAOYSA-N n-(1,3,4-thiadiazol-2-yl)benzamide Chemical compound C=1C=CC=CC=1C(=O)NC1=NN=CS1 RWOUBULBQYRRNL-UHFFFAOYSA-N 0.000 title 1
- 239000001257 hydrogen Substances 0.000 claims description 18
- 229910052739 hydrogen Inorganic materials 0.000 claims description 18
- 150000002431 hydrogen Chemical class 0.000 claims description 17
- -1 3-fluorophenyl 4-pyridyl Chemical group 0.000 claims description 13
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 8
- 229910052794 bromium Inorganic materials 0.000 claims description 8
- 229910052801 chlorine Inorganic materials 0.000 claims description 8
- 239000000460 chlorine Substances 0.000 claims description 8
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 8
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 7
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 6
- 229910052731 fluorine Inorganic materials 0.000 claims 6
- 239000011737 fluorine Substances 0.000 claims 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 2
- 229910052760 oxygen Inorganic materials 0.000 claims 2
- 239000001301 oxygen Substances 0.000 claims 2
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 1
- 125000001246 bromo group Chemical group Br* 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical group II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims 1
- QJQYPZZUKLQGGT-UHFFFAOYSA-N methyl hypobromite Chemical group COBr QJQYPZZUKLQGGT-UHFFFAOYSA-N 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- 239000011593 sulfur Substances 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 description 7
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- OAVULPOOAHQYDZ-UHFFFAOYSA-N 5-(4-chlorophenyl)-1,3,4-thiadiazol-2-amine Chemical compound S1C(N)=NN=C1C1=CC=C(Cl)C=C1 OAVULPOOAHQYDZ-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-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
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 230000010933 acylation Effects 0.000 description 3
- 238000005917 acylation reaction Methods 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-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
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-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
- 239000002253 acid Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 239000012312 sodium hydride Substances 0.000 description 2
- 229910000104 sodium hydride Inorganic materials 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 150000004869 1,3,4-thiadiazoles Chemical class 0.000 description 1
- JBLIDPPHFGWTKU-UHFFFAOYSA-N 2,6-dichlorobenzoyl chloride Chemical compound ClC(=O)C1=C(Cl)C=CC=C1Cl JBLIDPPHFGWTKU-UHFFFAOYSA-N 0.000 description 1
- FQUOYEHJJRUIQC-UHFFFAOYSA-N 3-(5-amino-1,3,4-thiadiazol-2-yl)phenol Chemical compound S1C(N)=NN=C1C1=CC=CC(O)=C1 FQUOYEHJJRUIQC-UHFFFAOYSA-N 0.000 description 1
- 125000004208 3-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C([H])C(*)=C1[H] 0.000 description 1
- 125000000242 4-chlorobenzoyl group Chemical group ClC1=CC=C(C(=O)*)C=C1 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 238000004566 IR spectroscopy Methods 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 239000003929 acidic solution Substances 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 125000004618 benzofuryl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 125000001475 halogen functional group Chemical group 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 238000004452 microanalysis Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 238000006213 oxygenation reaction Methods 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 239000003039 volatile agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/01—Five-membered rings
- C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
- C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
- C07D285/12—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles
- C07D285/125—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical
- C07D285/135—Nitrogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Plural Heterocyclic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US65655276A | 1976-02-09 | 1976-02-09 | |
| US74016676A | 1976-11-10 | 1976-11-10 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU706023A3 true SU706023A3 (ru) | 1979-12-25 |
Family
ID=27097215
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU772446348A SU706023A3 (ru) | 1976-02-09 | 1977-02-01 | Способ получени производных -(1,3,4-тиадиазол-2ил) бензамида |
Country Status (30)
| Country | Link |
|---|---|
| JP (1) | JPS52105173A (https=) |
| AR (1) | AR221204A1 (https=) |
| AT (1) | AT362192B (https=) |
| AU (1) | AU505649B2 (https=) |
| BG (3) | BG28987A4 (https=) |
| BR (1) | BR7700471A (https=) |
| CA (1) | CA1077041A (https=) |
| CH (1) | CH631603A5 (https=) |
| CS (1) | CS198217B2 (https=) |
| DD (2) | DD130038A5 (https=) |
| DE (1) | DE2704288A1 (https=) |
| DK (1) | DK50677A (https=) |
| ES (2) | ES455409A1 (https=) |
| FR (1) | FR2340312A1 (https=) |
| GB (1) | GB1571422A (https=) |
| GR (1) | GR65893B (https=) |
| HK (1) | HK27081A (https=) |
| HU (1) | HU179458B (https=) |
| IE (1) | IE44573B1 (https=) |
| IL (1) | IL51149A (https=) |
| IT (1) | IT1078058B (https=) |
| KE (1) | KE3131A (https=) |
| MY (1) | MY8200038A (https=) |
| NL (1) | NL7701059A (https=) |
| NZ (1) | NZ182937A (https=) |
| PL (2) | PL113231B1 (https=) |
| PT (1) | PT66158A (https=) |
| RO (2) | RO76588A (https=) |
| SE (1) | SE412063B (https=) |
| SU (1) | SU706023A3 (https=) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2606641C2 (ru) * | 2010-08-31 | 2017-01-10 | ДАУ АГРОСАЙЕНСИЗ ЭлЭлСи | Пестицидные композиции |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2639910A1 (en) | 2006-01-25 | 2007-08-02 | Synta Pharmaceuticals Corp. | Thiazole and thiadiazole compounds for inflammation and immune-related uses |
| EP2107054A1 (en) * | 2008-04-01 | 2009-10-07 | Università Degli Studi Di Milano - Bicocca | Antiproliferative compounds and therapeutic uses thereof |
| EP2558458B1 (de) | 2010-04-16 | 2017-09-06 | Bayer Intellectual Property GmbH | Neue heterocyclische verbindungen als schädlingsbekämpfungsmittel |
| JPWO2012121168A1 (ja) * | 2011-03-04 | 2014-07-17 | 国立大学法人京都大学 | キナーゼ阻害剤 |
| WO2014060381A1 (de) | 2012-10-18 | 2014-04-24 | Bayer Cropscience Ag | Heterocyclische verbindungen als schädlingsbekämpfungsmittel |
| TWI647222B (zh) * | 2014-03-06 | 2019-01-11 | 德商拜耳作物科學股份有限公司 | 作為殺蟲劑之雜環化合物 |
| CN110382493A (zh) * | 2016-12-16 | 2019-10-25 | 拜耳农作物科学股份公司 | 作为农药的噻二唑衍生物 |
| CN110267950A (zh) * | 2016-12-22 | 2019-09-20 | 拜耳作物科学股份公司 | 取代的杂芳基吡咯酮及其盐和其作为除草活性物质的用途 |
| CN109456283B (zh) * | 2018-12-13 | 2023-03-28 | 贵州大学 | 含1,3,4-噻二唑硫醚(砜)的2-(三氟甲基)苯甲酰胺类衍生物、其制备及应用 |
-
1976
- 1976-12-18 GR GR52438A patent/GR65893B/el unknown
- 1976-12-20 IE IE2783/76A patent/IE44573B1/en unknown
- 1976-12-21 NZ NZ182937A patent/NZ182937A/xx unknown
- 1976-12-22 CA CA268,463A patent/CA1077041A/en not_active Expired
- 1976-12-23 IL IL51149A patent/IL51149A/xx unknown
-
1977
- 1977-01-11 AR AR266147A patent/AR221204A1/es active
- 1977-01-25 SE SE7700778A patent/SE412063B/xx unknown
- 1977-01-26 BR BR7700471A patent/BR7700471A/pt unknown
- 1977-01-27 ES ES455409A patent/ES455409A1/es not_active Expired
- 1977-02-01 SU SU772446348A patent/SU706023A3/ru active
- 1977-02-02 NL NL7701059A patent/NL7701059A/xx not_active Application Discontinuation
- 1977-02-02 DE DE19772704288 patent/DE2704288A1/de not_active Ceased
- 1977-02-03 BG BG037894A patent/BG28987A4/xx unknown
- 1977-02-03 GB GB4389/77A patent/GB1571422A/en not_active Expired
- 1977-02-03 BG BG035326A patent/BG28236A3/xx unknown
- 1977-02-03 BG BG037893A patent/BG28986A4/xx unknown
- 1977-02-04 PT PT66158A patent/PT66158A/pt unknown
- 1977-02-07 HU HU77EI725A patent/HU179458B/hu unknown
- 1977-02-07 CH CH146977A patent/CH631603A5/de not_active IP Right Cessation
- 1977-02-07 DK DK50677A patent/DK50677A/da not_active Application Discontinuation
- 1977-02-07 AU AU22026/77A patent/AU505649B2/en not_active Expired
- 1977-02-08 AT AT81877A patent/AT362192B/de not_active IP Right Cessation
- 1977-02-08 CS CS77822A patent/CS198217B2/cs unknown
- 1977-02-08 IT IT20057/77A patent/IT1078058B/it active
- 1977-02-09 JP JP1404977A patent/JPS52105173A/ja active Pending
- 1977-02-09 PL PL1977220785A patent/PL113231B1/pl unknown
- 1977-02-09 PL PL1977195892A patent/PL112645B1/pl unknown
- 1977-02-09 DD DD7700197305A patent/DD130038A5/xx unknown
- 1977-02-09 DD DD77204378A patent/DD135032A5/xx unknown
- 1977-02-09 FR FR7703603A patent/FR2340312A1/fr active Granted
- 1977-02-13 RO RO7796600A patent/RO76588A/ro unknown
-
1978
- 1978-02-16 ES ES467061A patent/ES467061A1/es not_active Expired
-
1979
- 1979-02-17 RO RO7996599A patent/RO76587A/ro unknown
-
1981
- 1981-06-02 KE KE3131A patent/KE3131A/xx unknown
- 1981-06-18 HK HK270/81A patent/HK27081A/xx unknown
-
1982
- 1982-12-30 MY MY38/82A patent/MY8200038A/xx unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2606641C2 (ru) * | 2010-08-31 | 2017-01-10 | ДАУ АГРОСАЙЕНСИЗ ЭлЭлСи | Пестицидные композиции |
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