SU645578A3 - Способ получени производных тиазолинилкетобензимидазола - Google Patents
Способ получени производных тиазолинилкетобензимидазолаInfo
- Publication number
- SU645578A3 SU645578A3 SU762390303A SU2390303A SU645578A3 SU 645578 A3 SU645578 A3 SU 645578A3 SU 762390303 A SU762390303 A SU 762390303A SU 2390303 A SU2390303 A SU 2390303A SU 645578 A3 SU645578 A3 SU 645578A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- amino
- mixture
- added
- mol
- product
- Prior art date
Links
- 238000000034 method Methods 0.000 title description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 39
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 27
- 239000000203 mixture Substances 0.000 description 22
- 239000000047 product Substances 0.000 description 22
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 21
- 239000000243 solution Substances 0.000 description 19
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- 239000011541 reaction mixture Substances 0.000 description 15
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- 239000007787 solid Substances 0.000 description 12
- 238000003756 stirring Methods 0.000 description 12
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 239000000706 filtrate Substances 0.000 description 8
- 239000012312 sodium hydride Substances 0.000 description 8
- 229910000104 sodium hydride Inorganic materials 0.000 description 8
- 125000004301 thiazolin-2-yl group Chemical group [H]C1([H])SC(*)=NC1([H])[H] 0.000 description 8
- -1 haloethyl isothiocyanate Chemical class 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 5
- 229910052794 bromium Inorganic materials 0.000 description 5
- 239000003153 chemical reaction reagent Substances 0.000 description 5
- 239000001257 hydrogen Substances 0.000 description 5
- 229910052739 hydrogen Inorganic materials 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- HMVJXTUUQJUYJI-UHFFFAOYSA-N (3,4-diaminophenyl)methanol Chemical compound NC1=CC=C(CO)C=C1N HMVJXTUUQJUYJI-UHFFFAOYSA-N 0.000 description 4
- YOROYHPRNGLSAT-UHFFFAOYSA-N (4-amino-3-nitrophenyl)methanol Chemical compound NC1=CC=C(CO)C=C1[N+]([O-])=O YOROYHPRNGLSAT-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 239000002480 mineral oil Substances 0.000 description 4
- 235000010446 mineral oil Nutrition 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid group Chemical class S(O)(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- QAGYVZXMTCRIBM-UHFFFAOYSA-N 3h-benzimidazol-5-yl(thiophen-2-yl)methanone Chemical compound C=1C=C2N=CNC2=CC=1C(=O)C1=CC=CS1 QAGYVZXMTCRIBM-UHFFFAOYSA-N 0.000 description 3
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- 150000001450 anions Chemical class 0.000 description 3
- 150000001556 benzimidazoles Chemical class 0.000 description 3
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- RXCOGDYOZQGGMK-UHFFFAOYSA-N (3,4-diaminophenyl)-phenylmethanone Chemical compound C1=C(N)C(N)=CC=C1C(=O)C1=CC=CC=C1 RXCOGDYOZQGGMK-UHFFFAOYSA-N 0.000 description 2
- NGOOFAMQPUEDJM-UHFFFAOYSA-N (4-amino-3-nitrophenyl)-phenylmethanone Chemical compound C1=C([N+]([O-])=O)C(N)=CC=C1C(=O)C1=CC=CC=C1 NGOOFAMQPUEDJM-UHFFFAOYSA-N 0.000 description 2
- OELFHUHQZUESIQ-UHFFFAOYSA-N (4-chloro-3-nitrophenyl)-thiophen-2-ylmethanone Chemical compound C1=C(Cl)C([N+](=O)[O-])=CC(C(=O)C=2SC=CC=2)=C1 OELFHUHQZUESIQ-UHFFFAOYSA-N 0.000 description 2
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- CAQWNKXTMBFBGI-UHFFFAOYSA-N C.[Na] Chemical compound C.[Na] CAQWNKXTMBFBGI-UHFFFAOYSA-N 0.000 description 2
- 238000005727 Friedel-Crafts reaction Methods 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
- 239000003810 Jones reagent Substances 0.000 description 2
- FZERHIULMFGESH-UHFFFAOYSA-N N-phenylacetamide Chemical compound CC(=O)NC1=CC=CC=C1 FZERHIULMFGESH-UHFFFAOYSA-N 0.000 description 2
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- MYONAGGJKCJOBT-UHFFFAOYSA-N benzimidazol-2-one Chemical compound C1=CC=CC2=NC(=O)N=C21 MYONAGGJKCJOBT-UHFFFAOYSA-N 0.000 description 2
- ATDGTVJJHBUTRL-UHFFFAOYSA-N cyanogen bromide Chemical compound BrC#N ATDGTVJJHBUTRL-UHFFFAOYSA-N 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 150000004678 hydrides Chemical class 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- WECHHDJTILFYQT-UHFFFAOYSA-N n-(4-acetylphenyl)acetamide Chemical compound CC(=O)NC1=CC=C(C(C)=O)C=C1 WECHHDJTILFYQT-UHFFFAOYSA-N 0.000 description 2
- BFNPQKPWCMCEOT-UHFFFAOYSA-N n-(4-benzoyl-2-nitrophenyl)acetamide Chemical compound C1=C([N+]([O-])=O)C(NC(=O)C)=CC=C1C(=O)C1=CC=CC=C1 BFNPQKPWCMCEOT-UHFFFAOYSA-N 0.000 description 2
- OBEXUAPBTUTPDV-UHFFFAOYSA-N n-(4-benzoylphenyl)acetamide Chemical compound C1=CC(NC(=O)C)=CC=C1C(=O)C1=CC=CC=C1 OBEXUAPBTUTPDV-UHFFFAOYSA-N 0.000 description 2
- 229910052759 nickel Inorganic materials 0.000 description 2
- JMANVNJQNLATNU-UHFFFAOYSA-N oxalonitrile Chemical compound N#CC#N JMANVNJQNLATNU-UHFFFAOYSA-N 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- JYEFXNUTHWKKGY-UHFFFAOYSA-N (4-amino-3-nitrophenyl)-thiophen-2-ylmethanone Chemical compound C1=C([N+]([O-])=O)C(N)=CC=C1C(=O)C1=CC=CS1 JYEFXNUTHWKKGY-UHFFFAOYSA-N 0.000 description 1
- RBKHNGHPZZZJCI-UHFFFAOYSA-N (4-aminophenyl)-phenylmethanone Chemical compound C1=CC(N)=CC=C1C(=O)C1=CC=CC=C1 RBKHNGHPZZZJCI-UHFFFAOYSA-N 0.000 description 1
- QLLRQJDSYJIXTN-UHFFFAOYSA-N (4-chloro-3-nitrophenyl)methanol Chemical compound OCC1=CC=C(Cl)C([N+]([O-])=O)=C1 QLLRQJDSYJIXTN-UHFFFAOYSA-N 0.000 description 1
- UYFMRVDIXXOWLR-UHFFFAOYSA-N 1-(1h-benzimidazol-2-yl)ethanone Chemical compound C1=CC=C2NC(C(=O)C)=NC2=C1 UYFMRVDIXXOWLR-UHFFFAOYSA-N 0.000 description 1
- ZUWFBQUHBOUPFK-UHFFFAOYSA-N 1-chloro-2-isothiocyanatoethane Chemical compound ClCCN=C=S ZUWFBQUHBOUPFK-UHFFFAOYSA-N 0.000 description 1
- GPMHHSJZGVOEFS-UHFFFAOYSA-N 2-Amino-5-benzoylbenzimidazole Chemical compound C1=C2NC(N)=NC2=CC=C1C(=O)C1=CC=CC=C1 GPMHHSJZGVOEFS-UHFFFAOYSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 description 1
- JWYUFVNJZUSCSM-UHFFFAOYSA-N 2-aminobenzimidazole Chemical class C1=CC=C2NC(N)=NC2=C1 JWYUFVNJZUSCSM-UHFFFAOYSA-N 0.000 description 1
- APVQNDRXQVWGKX-UHFFFAOYSA-N 2-nitrosoaniline Chemical class NC1=CC=CC=C1N=O APVQNDRXQVWGKX-UHFFFAOYSA-N 0.000 description 1
- KROFADHHHXIPDD-UHFFFAOYSA-N 4,5-diaminocyclohexa-2,4-dien-1-one Chemical compound NC1=C(N)C=CC(=O)C1 KROFADHHHXIPDD-UHFFFAOYSA-N 0.000 description 1
- MLCYDVREEAHNTI-UHFFFAOYSA-N 4-amino-5-nitrocyclohexa-2,4-dien-1-one Chemical compound NC1=C([N+]([O-])=O)CC(=O)C=C1 MLCYDVREEAHNTI-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- FWDBZJBJTDRIIY-UHFFFAOYSA-N CC(C)(C)[K] Chemical compound CC(C)(C)[K] FWDBZJBJTDRIIY-UHFFFAOYSA-N 0.000 description 1
- 241000189662 Calla Species 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 241001139947 Mida Species 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- MJOVZNXYZWBZCZ-UHFFFAOYSA-N [2-amino-3-(4,5-dihydro-1,3-thiazol-2-yl)benzimidazol-5-yl]-phenylmethanone Chemical compound NC1=NC2=CC=C(C(=O)C=3C=CC=CC=3)C=C2N1C1=NCCS1 MJOVZNXYZWBZCZ-UHFFFAOYSA-N 0.000 description 1
- 229960001413 acetanilide Drugs 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 238000005915 ammonolysis reaction Methods 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 235000019445 benzyl alcohol Nutrition 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 150000001793 charged compounds Chemical class 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 239000002026 chloroform extract Substances 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- UZZWBUYVTBPQIV-UHFFFAOYSA-N dme dimethoxyethane Chemical compound COCCOC.COCCOC UZZWBUYVTBPQIV-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- 230000008570 general process Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- VBEGHXKAFSLLGE-UHFFFAOYSA-N n-phenylnitramide Chemical compound [O-][N+](=O)NC1=CC=CC=C1 VBEGHXKAFSLLGE-UHFFFAOYSA-N 0.000 description 1
- 238000006396 nitration reaction Methods 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- MTHMVLLKCNMJQL-UHFFFAOYSA-N oxalonitrile hydrobromide Chemical compound Br.N#CC#N MTHMVLLKCNMJQL-UHFFFAOYSA-N 0.000 description 1
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229910003446 platinum oxide Inorganic materials 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- ZWZVWGITAAIFPS-UHFFFAOYSA-N thiophosgene Chemical compound ClC(Cl)=S ZWZVWGITAAIFPS-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US62601475A | 1975-10-28 | 1975-10-28 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU645578A3 true SU645578A3 (ru) | 1979-01-30 |
Family
ID=24508599
Family Applications (4)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU762390303A SU645578A3 (ru) | 1975-10-28 | 1976-08-26 | Способ получени производных тиазолинилкетобензимидазола |
| SU772521749A SU701540A3 (ru) | 1975-10-28 | 1977-09-13 | Способ получени производных тиазолинил-кетобензимидазола |
| SU772520768A SU685154A3 (ru) | 1975-10-28 | 1977-09-14 | Способ получени производных тиазолинилкетобензимидазола |
| SU772522951A SU719502A3 (ru) | 1975-10-28 | 1977-09-22 | Способ получени производных тиазолинилкетобензимидазолов |
Family Applications After (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU772521749A SU701540A3 (ru) | 1975-10-28 | 1977-09-13 | Способ получени производных тиазолинил-кетобензимидазола |
| SU772520768A SU685154A3 (ru) | 1975-10-28 | 1977-09-14 | Способ получени производных тиазолинилкетобензимидазола |
| SU772522951A SU719502A3 (ru) | 1975-10-28 | 1977-09-22 | Способ получени производных тиазолинилкетобензимидазолов |
Country Status (19)
| Country | Link |
|---|---|
| AR (5) | AR213509A1 (enExample) |
| BG (1) | BG27549A3 (enExample) |
| CS (3) | CS194775B2 (enExample) |
| DD (1) | DD126517A5 (enExample) |
| DK (1) | DK145343C (enExample) |
| ES (4) | ES451019A1 (enExample) |
| GR (1) | GR61292B (enExample) |
| HU (1) | HU174433B (enExample) |
| IE (1) | IE43318B1 (enExample) |
| IL (1) | IL50293A (enExample) |
| MX (1) | MX3780E (enExample) |
| NZ (1) | NZ181787A (enExample) |
| PH (1) | PH14754A (enExample) |
| PL (3) | PL108068B1 (enExample) |
| PT (1) | PT65487B (enExample) |
| RO (4) | RO77753A (enExample) |
| SU (4) | SU645578A3 (enExample) |
| YU (1) | YU203376A (enExample) |
| ZA (1) | ZA765144B (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2365672C1 (ru) * | 2007-12-27 | 2009-08-27 | Государственное образовательное учреждение высшего профессионального образования "Московский Инженерно-Физический Институт (государственный университет)" | Способ получения антифрикционных тонких пленок |
-
1976
- 1976-08-17 PT PT65487A patent/PT65487B/pt unknown
- 1976-08-17 MX MX763668U patent/MX3780E/es unknown
- 1976-08-17 NZ NZ181787A patent/NZ181787A/xx unknown
- 1976-08-17 GR GR51489A patent/GR61292B/el unknown
- 1976-08-18 HU HU76EI692A patent/HU174433B/hu unknown
- 1976-08-18 IL IL50293A patent/IL50293A/xx unknown
- 1976-08-19 YU YU02033/76A patent/YU203376A/xx unknown
- 1976-08-19 AR AR264378A patent/AR213509A1/es active
- 1976-08-24 CS CS765493A patent/CS194775B2/cs unknown
- 1976-08-24 CS CS761070A patent/CS194799B2/cs unknown
- 1976-08-24 CS CS781069A patent/CS194798B2/cs unknown
- 1976-08-24 IE IE1882/76A patent/IE43318B1/en unknown
- 1976-08-25 RO RO7698539A patent/RO77753A/ro unknown
- 1976-08-25 RO RO7687358A patent/RO72057A/ro unknown
- 1976-08-25 RO RO7698537A patent/RO77751A/ro unknown
- 1976-08-25 RO RO7698538A patent/RO77752A/ro unknown
- 1976-08-26 DK DK386176A patent/DK145343C/da not_active IP Right Cessation
- 1976-08-26 BG BG034081A patent/BG27549A3/xx unknown
- 1976-08-26 ES ES451019A patent/ES451019A1/es not_active Expired
- 1976-08-26 SU SU762390303A patent/SU645578A3/ru active
- 1976-08-27 ZA ZA00765144A patent/ZA765144B/xx unknown
- 1976-08-27 DD DD194503A patent/DD126517A5/xx unknown
- 1976-09-14 PL PL1976210979A patent/PL108068B1/pl unknown
- 1976-09-14 PL PL1976192394A patent/PL104540B1/pl unknown
- 1976-09-14 PL PL1976210978A patent/PL108038B1/pl unknown
-
1977
- 1977-02-18 AR AR266612A patent/AR219914A1/es active
- 1977-04-15 PH PH19677A patent/PH14754A/en unknown
- 1977-08-16 ES ES461637A patent/ES461637A1/es not_active Expired
- 1977-08-16 ES ES461636A patent/ES461636A1/es not_active Expired
- 1977-08-16 ES ES461635A patent/ES461635A1/es not_active Expired
- 1977-09-13 SU SU772521749A patent/SU701540A3/ru active
- 1977-09-14 SU SU772520768A patent/SU685154A3/ru active
- 1977-09-22 SU SU772522951A patent/SU719502A3/ru active
-
1978
- 1978-03-28 AR AR271573A patent/AR218298A1/es active
- 1978-03-28 AR AR271571A patent/AR215688A1/es active
- 1978-03-28 AR AR271572A patent/AR219102A1/es active
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2365672C1 (ru) * | 2007-12-27 | 2009-08-27 | Государственное образовательное учреждение высшего профессионального образования "Московский Инженерно-Физический Институт (государственный университет)" | Способ получения антифрикционных тонких пленок |
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| SU691089A3 (ru) | Способ получени карбонилзамещенных 1-сульфонилбензимидазолов | |
| EP0115248B1 (de) | Substituierte 5H-Pyrimido(5,4-b)indole | |
| SU447886A1 (ru) | Способ получени защищенной 4,6-0-алкилиден- - -глюкопиранозы | |
| Huebner | Studies of imidazole compounds. V. A new and improved synthesis of 4-(2-substituted aminoethyl)-imidazoles | |
| SU645578A3 (ru) | Способ получени производных тиазолинилкетобензимидазола | |
| US4950770A (en) | Psoralens aminomethylation | |
| US3042684A (en) | J-ethtl-jj-nitrovinylindole | |
| Galvez et al. | Functional derivatives of thiophene. I. Synthesis and 1H‐NMR spectra in the 2‐aminothiophene series | |
| US3972894A (en) | Synthesis of oxindoles from anilines and β-thio carboxylic esters or amides | |
| US3024243A (en) | New derivatives of pyrrolopyridines and pyrroloquinolines and methods of preparing the same | |
| US3966758A (en) | Anti-inflammatory 1-(substituted benzyl)-2-imidazolidinones | |
| Grischuk et al. | 4-Thionazolidones, derivatives and analogs: III. Synthesis and reactions of 4-thionthiazolid-2-one (isorhodanine) | |
| US3455948A (en) | 2-aminobenzimidazole and a process for preparing 2-aminobenzimidazoles | |
| ELDERFIELD et al. | SYNTHESIS OF 1-AMINOPHENAZINES AND CONVERSION OF THEM TO POTENTIAL ANTIMALARIALS1 | |
| IL24192A (en) | 1-phenylsulfonyl-2-benzimidazolinones and 1-phenylsulfonyl-2-benzimidazolinethiones and process for their preparation | |
| Kandeel | Nitriles in heterocyclic synthesis: A novel synthesis of some thieno [2, 3‐d] pyrimidine and thieno [2, 3‐b] pyridine derivatives | |
| US4186132A (en) | Isatin products | |
| SU591140A3 (ru) | Способ получени 2-(3"-метокси4"-гидроксифенил)-индола | |
| JPS62228058A (ja) | 新規イソインドリン誘導体及びその製造法 | |
| CN116768881B (zh) | 4-(3-吲哚基)-1,3-噻唑类化合物及其制备方法和应用 | |
| US3314951A (en) | Spiro(indoline-3, 2'-[2h-1, 3]thiazin)-2-ones and derivatives thereof | |
| US3347864A (en) | Production of aminoquinolines | |
| SU436057A1 (ru) | СПОСОБ ПОЛУЧЕНИЯ ИЗОПРОПИЛИДЕНОВЫХ ПРОИЗВОДНЫХ ПИРИДОКСИНАВ ПТ5ФОНЯ mmim | |
| Chkhikvadze et al. | 5-Substituted pyrimidine derivatives: II. Synthesis of 5, 6-dihydropyrrolo [2, 3-d] pyrimidines (5, 7-diazaindolines) | |
| DeGraw | THE SYNTHESIS OF 5-DIMETHYLAMINOINDOLE AND DERIVATIVES |