RU2495869C2 - Способ получения производных 2-амино-5-цианобензойной кислоты - Google Patents
Способ получения производных 2-амино-5-цианобензойной кислоты Download PDFInfo
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- RU2495869C2 RU2495869C2 RU2010140605/04A RU2010140605A RU2495869C2 RU 2495869 C2 RU2495869 C2 RU 2495869C2 RU 2010140605/04 A RU2010140605/04 A RU 2010140605/04A RU 2010140605 A RU2010140605 A RU 2010140605A RU 2495869 C2 RU2495869 C2 RU 2495869C2
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- Prior art keywords
- formula
- reagent
- compound
- imidazole
- mixture
- Prior art date
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- 238000000034 method Methods 0.000 title claims abstract description 251
- HQNZNIJPAYTWJK-UHFFFAOYSA-N 2-amino-5-cyanobenzoic acid Chemical class NC1=CC=C(C#N)C=C1C(O)=O HQNZNIJPAYTWJK-UHFFFAOYSA-N 0.000 title abstract description 5
- 239000003153 chemical reaction reagent Substances 0.000 claims abstract description 210
- 150000001875 compounds Chemical class 0.000 claims abstract description 206
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 claims abstract description 63
- -1 alkali metal cyanide Chemical class 0.000 claims abstract description 39
- VMQMZMRVKUZKQL-UHFFFAOYSA-N Cu+ Chemical class [Cu+] VMQMZMRVKUZKQL-UHFFFAOYSA-N 0.000 claims abstract description 35
- 229910052751 metal Inorganic materials 0.000 claims abstract description 35
- 239000002184 metal Substances 0.000 claims abstract description 35
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical class I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims abstract description 27
- 229910052783 alkali metal Inorganic materials 0.000 claims abstract description 25
- 229910052794 bromium Inorganic materials 0.000 claims abstract description 14
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 13
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 12
- DOBRDRYODQBAMW-UHFFFAOYSA-N copper(i) cyanide Chemical compound [Cu+].N#[C-] DOBRDRYODQBAMW-UHFFFAOYSA-N 0.000 claims abstract description 11
- 125000006450 cyclopropyl cyclopropyl group Chemical group 0.000 claims abstract description 10
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims abstract description 10
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims abstract description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 9
- 125000006431 methyl cyclopropyl group Chemical group 0.000 claims abstract description 7
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 6
- 239000000203 mixture Substances 0.000 claims description 89
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 69
- 239000002904 solvent Substances 0.000 claims description 62
- 239000003960 organic solvent Substances 0.000 claims description 51
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 50
- 239000007787 solid Substances 0.000 claims description 42
- AUHZEENZYGFFBQ-UHFFFAOYSA-N 1,3,5-trimethylbenzene Chemical compound CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 claims description 37
- UOCPQZOXOQZEGV-UHFFFAOYSA-N 2-amino-5-cyano-n,3-dimethylbenzamide Chemical compound CNC(=O)C1=CC(C#N)=CC(C)=C1N UOCPQZOXOQZEGV-UHFFFAOYSA-N 0.000 claims description 35
- 150000003839 salts Chemical class 0.000 claims description 33
- 238000003756 stirring Methods 0.000 claims description 29
- KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 claims description 28
- MCMFEZDRQOJKMN-UHFFFAOYSA-N 1-butylimidazole Chemical compound CCCCN1C=CN=C1 MCMFEZDRQOJKMN-UHFFFAOYSA-N 0.000 claims description 27
- 239000008096 xylene Substances 0.000 claims description 25
- 150000003738 xylenes Chemical class 0.000 claims description 25
- QPUYECUOLPXSFR-UHFFFAOYSA-N 1-methylnaphthalene Chemical compound C1=CC=C2C(C)=CC=CC2=C1 QPUYECUOLPXSFR-UHFFFAOYSA-N 0.000 claims description 22
- 229940071870 hydroiodic acid Drugs 0.000 claims description 19
- 229910052799 carbon Inorganic materials 0.000 claims description 17
- XLSZMDLNRCVEIJ-UHFFFAOYSA-N 4-methylimidazole Chemical compound CC1=CNC=N1 XLSZMDLNRCVEIJ-UHFFFAOYSA-N 0.000 claims description 16
- MCTWTZJPVLRJOU-UHFFFAOYSA-N 1-methyl-1H-imidazole Chemical compound CN1C=CN=C1 MCTWTZJPVLRJOU-UHFFFAOYSA-N 0.000 claims description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims description 15
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 claims description 14
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 14
- GWHJZXXIDMPWGX-UHFFFAOYSA-N 1,2,4-trimethylbenzene Chemical compound CC1=CC=C(C)C(C)=C1 GWHJZXXIDMPWGX-UHFFFAOYSA-N 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- 238000001816 cooling Methods 0.000 claims description 10
- CHRPUSCNMSNSKL-UHFFFAOYSA-N 1,1'-hexane-1,6-diylbis(1h-imidazole) Chemical compound C1=CN=CN1CCCCCCN1C=CN=C1 CHRPUSCNMSNSKL-UHFFFAOYSA-N 0.000 claims description 9
- LGCPYQSYWVJQCJ-UHFFFAOYSA-N 1-(4-imidazol-1-ylbutyl)imidazole Chemical compound C1=CN=CN1CCCCN1C=CN=C1 LGCPYQSYWVJQCJ-UHFFFAOYSA-N 0.000 claims description 7
- IWDFHWZHHOSSGR-UHFFFAOYSA-N 1-ethylimidazole Chemical compound CCN1C=CN=C1 IWDFHWZHHOSSGR-UHFFFAOYSA-N 0.000 claims description 7
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 claims description 7
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 claims description 7
- 125000001424 substituent group Chemical group 0.000 claims description 7
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 claims description 6
- CRVLLZCRVARGGG-UHFFFAOYSA-N 1-(5-imidazol-1-ylpentyl)imidazole Chemical compound C1=CN=CN1CCCCCN1C=CN=C1 CRVLLZCRVARGGG-UHFFFAOYSA-N 0.000 claims description 5
- IYVYLVCVXXCYRI-UHFFFAOYSA-N 1-propylimidazole Chemical compound CCCN1C=CN=C1 IYVYLVCVXXCYRI-UHFFFAOYSA-N 0.000 claims description 5
- KGWVFQAPOGAVRF-UHFFFAOYSA-N 1-hexylimidazole Chemical compound CCCCCCN1C=CN=C1 KGWVFQAPOGAVRF-UHFFFAOYSA-N 0.000 claims description 4
- UPYVYJSWGZMBOU-UHFFFAOYSA-N 1-pentylimidazole Chemical compound CCCCCN1C=CN=C1 UPYVYJSWGZMBOU-UHFFFAOYSA-N 0.000 claims description 4
- 150000001879 copper Chemical class 0.000 claims description 3
- 150000002790 naphthalenes Chemical class 0.000 claims description 3
- NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 claims description 3
- GBRBMTNGQBKBQE-UHFFFAOYSA-L copper;diiodide Chemical compound I[Cu]I GBRBMTNGQBKBQE-UHFFFAOYSA-L 0.000 claims 1
- 239000000126 substance Substances 0.000 abstract description 12
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 abstract 1
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 1
- 239000011541 reaction mixture Substances 0.000 description 88
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 77
- 238000006243 chemical reaction Methods 0.000 description 64
- 239000000376 reactant Substances 0.000 description 58
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 39
- 229910052757 nitrogen Inorganic materials 0.000 description 38
- 239000007789 gas Substances 0.000 description 34
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 30
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 30
- KGZYALLFLANLBU-UHFFFAOYSA-N 2-amino-5-bromo-n,3-dimethylbenzamide Chemical compound CNC(=O)C1=CC(Br)=CC(C)=C1N KGZYALLFLANLBU-UHFFFAOYSA-N 0.000 description 29
- 229910021595 Copper(I) iodide Inorganic materials 0.000 description 26
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 26
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 25
- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 25
- LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 description 24
- 238000002360 preparation method Methods 0.000 description 24
- 239000000460 chlorine Substances 0.000 description 22
- 150000001412 amines Chemical class 0.000 description 20
- 239000002585 base Substances 0.000 description 20
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 19
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical group [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 17
- 150000002148 esters Chemical class 0.000 description 17
- 239000010949 copper Substances 0.000 description 16
- 239000000047 product Substances 0.000 description 16
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- 238000005481 NMR spectroscopy Methods 0.000 description 15
- 229910052802 copper Inorganic materials 0.000 description 15
- 238000002347 injection Methods 0.000 description 15
- 239000007924 injection Substances 0.000 description 15
- 229910000856 hastalloy Inorganic materials 0.000 description 14
- 239000012299 nitrogen atmosphere Substances 0.000 description 14
- 235000011121 sodium hydroxide Nutrition 0.000 description 14
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical class Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
- 238000004519 manufacturing process Methods 0.000 description 13
- 230000008569 process Effects 0.000 description 13
- 239000012429 reaction media Substances 0.000 description 13
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
- 239000002253 acid Substances 0.000 description 12
- 239000000243 solution Substances 0.000 description 12
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 12
- 238000004128 high performance liquid chromatography Methods 0.000 description 11
- 239000003446 ligand Substances 0.000 description 11
- 238000010992 reflux Methods 0.000 description 11
- 239000011734 sodium Substances 0.000 description 11
- PXBFMLJZNCDSMP-UHFFFAOYSA-N 2-Aminobenzamide Chemical class NC(=O)C1=CC=CC=C1N PXBFMLJZNCDSMP-UHFFFAOYSA-N 0.000 description 10
- 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 10
- 150000001735 carboxylic acids Chemical class 0.000 description 10
- 239000003795 chemical substances by application Substances 0.000 description 10
- 229910052708 sodium Inorganic materials 0.000 description 10
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 229960000583 acetic acid Drugs 0.000 description 9
- 230000014509 gene expression Effects 0.000 description 9
- 150000002825 nitriles Chemical group 0.000 description 9
- AWDBHOZBRXWRKS-UHFFFAOYSA-N tetrapotassium;iron(6+);hexacyanide Chemical compound [K+].[K+].[K+].[K+].[Fe+6].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-] AWDBHOZBRXWRKS-UHFFFAOYSA-N 0.000 description 9
- 238000009835 boiling Methods 0.000 description 8
- 238000002955 isolation Methods 0.000 description 8
- 239000000843 powder Substances 0.000 description 8
- 239000007858 starting material Substances 0.000 description 8
- ITQTTZVARXURQS-UHFFFAOYSA-N 3-methylpyridine Chemical compound CC1=CC=CN=C1 ITQTTZVARXURQS-UHFFFAOYSA-N 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical class [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 7
- 239000005708 Sodium hypochlorite Substances 0.000 description 7
- 235000011054 acetic acid Nutrition 0.000 description 7
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 7
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 7
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 7
- MZLKHPDPHGHSOY-UHFFFAOYSA-N (2,3-dioxoindole-1-carbonyl) 2,3-dioxoindole-1-carboxylate Chemical compound O=C1C(=O)C2=CC=CC=C2N1C(=O)OC(=O)N1C2=CC=CC=C2C(=O)C1=O MZLKHPDPHGHSOY-UHFFFAOYSA-N 0.000 description 6
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 239000012359 Methanesulfonyl chloride Substances 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 6
- 229910052731 fluorine Inorganic materials 0.000 description 6
- 125000000623 heterocyclic group Chemical group 0.000 description 6
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 6
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 6
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 6
- 150000003254 radicals Chemical class 0.000 description 6
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
- 0 *c(cc(cc1*)C#N)c1N Chemical compound *c(cc(cc1*)C#N)c1N 0.000 description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 5
- 150000007513 acids Chemical class 0.000 description 5
- 150000001340 alkali metals Chemical class 0.000 description 5
- RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical class NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 description 5
- 238000010790 dilution Methods 0.000 description 5
- 239000012895 dilution Substances 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- QHJMFSMPSZREIF-UHFFFAOYSA-N 1,3-dimethylnaphthalene Chemical compound C1=CC=CC2=CC(C)=CC(C)=C21 QHJMFSMPSZREIF-UHFFFAOYSA-N 0.000 description 4
- SDDBCEWUYXVGCQ-UHFFFAOYSA-N 1,5-dimethylnaphthalene Chemical compound C1=CC=C2C(C)=CC=CC2=C1C SDDBCEWUYXVGCQ-UHFFFAOYSA-N 0.000 description 4
- QIMMUPPBPVKWKM-UHFFFAOYSA-N 2-methylnaphthalene Chemical compound C1=CC=CC2=CC(C)=CC=C21 QIMMUPPBPVKWKM-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 4
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 4
- JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- 239000004809 Teflon Substances 0.000 description 4
- 229920006362 Teflon® Polymers 0.000 description 4
- 150000001408 amides Chemical group 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- 238000002425 crystallisation Methods 0.000 description 4
- 230000008025 crystallization Effects 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- 230000008020 evaporation Effects 0.000 description 4
- 238000000605 extraction Methods 0.000 description 4
- 238000000227 grinding Methods 0.000 description 4
- 230000002140 halogenating effect Effects 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 125000002883 imidazolyl group Chemical group 0.000 description 4
- 239000000543 intermediate Substances 0.000 description 4
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 4
- 238000010561 standard procedure Methods 0.000 description 4
- 150000003512 tertiary amines Chemical class 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- UAYWVJHJZHQCIE-UHFFFAOYSA-L zinc iodide Chemical compound I[Zn]I UAYWVJHJZHQCIE-UHFFFAOYSA-L 0.000 description 4
- TXJUTRJFNRYTHH-UHFFFAOYSA-N 1h-3,1-benzoxazine-2,4-dione Chemical compound C1=CC=C2C(=O)OC(=O)NC2=C1 TXJUTRJFNRYTHH-UHFFFAOYSA-N 0.000 description 3
- YGYNBBAUIYTWBF-UHFFFAOYSA-N 2,6-dimethylnaphthalene Chemical compound C1=C(C)C=CC2=CC(C)=CC=C21 YGYNBBAUIYTWBF-UHFFFAOYSA-N 0.000 description 3
- OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 3
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 239000005711 Benzoic acid Substances 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 3
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 3
- 239000004696 Poly ether ether ketone Substances 0.000 description 3
- 239000011260 aqueous acid Substances 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 235000010233 benzoic acid Nutrition 0.000 description 3
- 239000001569 carbon dioxide Substances 0.000 description 3
- 229910002092 carbon dioxide Inorganic materials 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 235000019253 formic acid Nutrition 0.000 description 3
- 238000007429 general method Methods 0.000 description 3
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- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- YODZTKMDCQEPHD-UHFFFAOYSA-N thiodiglycol Chemical compound OCCSCCO YODZTKMDCQEPHD-UHFFFAOYSA-N 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- UCPYLLCMEDAXFR-UHFFFAOYSA-N triphosgene Chemical compound ClC(Cl)(Cl)OC(=O)OC(Cl)(Cl)Cl UCPYLLCMEDAXFR-UHFFFAOYSA-N 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C253/00—Preparation of carboxylic acid nitriles
- C07C253/14—Preparation of carboxylic acid nitriles by reaction of cyanides with halogen-containing compounds with replacement of halogen atoms by cyano groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/49—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C255/58—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing cyano groups and singly-bound nitrogen atoms, not being further bound to other hetero atoms, bound to the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D231/16—Halogen atoms or nitro radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Toxicology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US6829708P | 2008-03-05 | 2008-03-05 | |
| US61/068,297 | 2008-03-05 | ||
| PCT/US2009/036012 WO2009111553A1 (en) | 2008-03-05 | 2009-03-04 | Process for preparing 2-amino-5-cyanobenzoic acid derivatives |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| RU2010140605A RU2010140605A (ru) | 2012-04-10 |
| RU2495869C2 true RU2495869C2 (ru) | 2013-10-20 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2010140605/04A RU2495869C2 (ru) | 2008-03-05 | 2009-03-04 | Способ получения производных 2-амино-5-цианобензойной кислоты |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US8242279B2 (enExample) |
| EP (1) | EP2254858B1 (enExample) |
| JP (1) | JP5480167B2 (enExample) |
| KR (1) | KR101609891B1 (enExample) |
| CN (1) | CN101965329B (enExample) |
| AR (1) | AR070803A1 (enExample) |
| BR (1) | BRPI0906098B8 (enExample) |
| CA (1) | CA2714409A1 (enExample) |
| CL (1) | CL2009000503A1 (enExample) |
| CO (1) | CO6290753A2 (enExample) |
| HU (1) | HUE032406T2 (enExample) |
| IL (1) | IL207526A (enExample) |
| MX (1) | MX2010009583A (enExample) |
| MY (1) | MY150514A (enExample) |
| RU (1) | RU2495869C2 (enExample) |
| TW (1) | TWI431000B (enExample) |
| UA (1) | UA105173C2 (enExample) |
| WO (1) | WO2009111553A1 (enExample) |
| ZA (1) | ZA201005350B (enExample) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TWI432421B (zh) | 2007-12-19 | 2014-04-01 | Du Pont | 製備２－胺基－５－氰基苯甲酸衍生物之方法 |
| HUE025309T2 (en) * | 2011-01-28 | 2016-01-28 | Du Pont | Process for the preparation of 2-aminobenzamide derivatives |
| EP2729444B1 (de) * | 2011-07-08 | 2017-08-23 | Bayer Intellectual Property GmbH | Verfahren zur herstellung von 2-amino-5-cyano-n,3-dimethylbenzamid |
| US8921567B2 (en) | 2011-08-12 | 2014-12-30 | Basf Se | Process for preparing N-substituted 1H-pyrazole-5-carbonylchloride compounds |
| MX2014001038A (es) | 2011-08-12 | 2014-03-27 | Basf Se | Compuestos tipo anilina. |
| CN103889960A (zh) | 2011-08-18 | 2014-06-25 | 巴斯夫欧洲公司 | 用于防治无脊椎动物害虫的氨基甲酰基甲氧基-和氨基甲酰基甲硫基-及氨基甲酰基甲基氨基苯甲酰胺 |
| US9199975B2 (en) | 2011-09-30 | 2015-12-01 | Asana Biosciences, Llc | Biaryl imidazole derivatives for regulating CYP17 |
| AU2012342564A1 (en) | 2011-11-21 | 2014-06-12 | Basf Se | Process for preparing N-substituted 1H-pyrazole-5-carboxylate compounds and derivatives thereof |
| BR112014019487A2 (pt) | 2012-02-07 | 2020-10-27 | Bayer Intellectual Property Gmbh | processo para preparar derivados de ácidos antranílico substituídos |
| CN103060837B (zh) * | 2013-01-29 | 2015-12-23 | 哈尔滨理工大学 | 一种2-氨基-5-溴-n,3-二甲基苯甲酰胺的制备方法 |
| KR20150135485A (ko) | 2013-03-28 | 2015-12-02 | 바스프 에스이 | 술피민의 제조 방법 및 술피민의 ｎ-（２-아미노-벤조일）-술피민으로의 제자리 전환 |
| TWI678354B (zh) | 2014-05-29 | 2019-12-01 | 新加坡商艾佛艾姆希農業新加坡有限公司 | 藉空氣氧化製備３-甲基-２-硝基苯甲酸之製程 |
| CN105461683B (zh) * | 2015-11-18 | 2019-01-15 | 江苏省农用激素工程技术研究中心有限公司 | 邻氨基苯甲酰胺化合物的制备方法 |
| CN108484572A (zh) * | 2018-04-29 | 2018-09-04 | 江苏省农用激素工程技术研究中心有限公司 | 新型双酰胺类化合物及其制备方法和应用 |
| US12234217B2 (en) * | 2018-12-03 | 2025-02-25 | Fmc Corporation | Method for preparing N-phenylpyrazole-1-carboxamides |
| WO2023012081A1 (en) | 2021-08-05 | 2023-02-09 | Syngenta Crop Protection Ag | Method for controlling diamide resistant pests & compounds therefor |
| CN114621144A (zh) * | 2022-03-23 | 2022-06-14 | 南开大学 | 一类氰基取代的苯基吡唑酰胺衍生物及其制备方法和用途 |
| CN120379959A (zh) | 2022-08-16 | 2025-07-25 | 安道麦马克西姆有限公司 | 用于经由氨基-氰基-苯衍生物制备溴氰虫酰胺的方法 |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2262231C1 (ru) * | 2001-08-13 | 2005-10-20 | Е.И.Дюпон Де Немур Энд Компани | Способ борьбы с конкретными насекомыми-вредителями путем нанесения антраниламидных соединений |
| WO2006068669A1 (en) * | 2004-07-26 | 2006-06-29 | E.I. Dupont De Nemours And Company | Mixtures of anthranilamide invertebrate pest control agents |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20050032107A (ko) | 2002-08-02 | 2005-04-06 | 메사추세츠 인스티튜트 오브 테크놀로지 | 구리를 촉매로 한 탄소-헤테로원자 결합 및 탄소-탄소결합 형성방법 |
| PT1599463E (pt) | 2003-01-28 | 2013-09-03 | Du Pont | Insecticidas à base de ciano-antranilamida |
| TWI363756B (en) * | 2004-12-07 | 2012-05-11 | Du Pont | Method for preparing n-phenylpyrazole-1-carboxamides |
| DE102006042439A1 (de) | 2006-09-09 | 2008-03-27 | Saltigo Gmbh | Verfahren zur katalytischen Herstellung von aromatischen oder heteroaromatischen Nitrilen |
| TWI415827B (zh) | 2006-12-21 | 2013-11-21 | Du Pont | 製備２-胺基-５-氰基苯甲酸衍生物之方法 |
| TWI432421B (zh) | 2007-12-19 | 2014-04-01 | Du Pont | 製備２－胺基－５－氰基苯甲酸衍生物之方法 |
-
2009
- 2009-02-25 TW TW098106032A patent/TWI431000B/zh active
- 2009-03-04 CL CL2009000503A patent/CL2009000503A1/es unknown
- 2009-03-04 CN CN200980106569.3A patent/CN101965329B/zh active Active
- 2009-03-04 KR KR1020107022122A patent/KR101609891B1/ko active Active
- 2009-03-04 EP EP09718451.9A patent/EP2254858B1/en active Active
- 2009-03-04 CA CA2714409A patent/CA2714409A1/en not_active Abandoned
- 2009-03-04 US US12/920,401 patent/US8242279B2/en active Active
- 2009-03-04 HU HUE09718451A patent/HUE032406T2/en unknown
- 2009-03-04 WO PCT/US2009/036012 patent/WO2009111553A1/en not_active Ceased
- 2009-03-04 BR BRPI0906098A patent/BRPI0906098B8/pt active IP Right Grant
- 2009-03-04 MY MYPI20103504 patent/MY150514A/en unknown
- 2009-03-04 RU RU2010140605/04A patent/RU2495869C2/ru active
- 2009-03-04 UA UAA201010673A patent/UA105173C2/uk unknown
- 2009-03-04 MX MX2010009583A patent/MX2010009583A/es active IP Right Grant
- 2009-03-04 JP JP2010549849A patent/JP5480167B2/ja active Active
- 2009-03-05 AR ARP090100791A patent/AR070803A1/es unknown
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- 2010-08-10 IL IL207526A patent/IL207526A/en active IP Right Grant
- 2010-09-03 CO CO10109228A patent/CO6290753A2/es not_active Application Discontinuation
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2262231C1 (ru) * | 2001-08-13 | 2005-10-20 | Е.И.Дюпон Де Немур Энд Компани | Способ борьбы с конкретными насекомыми-вредителями путем нанесения антраниламидных соединений |
| WO2006068669A1 (en) * | 2004-07-26 | 2006-06-29 | E.I. Dupont De Nemours And Company | Mixtures of anthranilamide invertebrate pest control agents |
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| Schareina Т. et al: "A state-of-the-art cyanation of aryl bromides: a novel and versatile cooper catalyst system inspired by nature", Chem. Eur. J. 2007, 13, pp.6249-6254. * |
Also Published As
| Publication number | Publication date |
|---|---|
| MX2010009583A (es) | 2010-09-24 |
| EP2254858B1 (en) | 2016-09-28 |
| IL207526A0 (en) | 2010-12-30 |
| KR101609891B1 (ko) | 2016-04-06 |
| HUE032406T2 (en) | 2017-09-28 |
| KR20100125384A (ko) | 2010-11-30 |
| BRPI0906098B1 (pt) | 2018-02-06 |
| TWI431000B (zh) | 2014-03-21 |
| AU2009221864A1 (en) | 2009-09-11 |
| US20110003998A1 (en) | 2011-01-06 |
| US8242279B2 (en) | 2012-08-14 |
| JP2011513422A (ja) | 2011-04-28 |
| BRPI0906098A2 (pt) | 2015-06-30 |
| MY150514A (en) | 2014-01-30 |
| CN101965329B (zh) | 2014-02-12 |
| EP2254858A1 (en) | 2010-12-01 |
| WO2009111553A1 (en) | 2009-09-11 |
| CN101965329A (zh) | 2011-02-02 |
| UA105173C2 (uk) | 2014-04-25 |
| RU2010140605A (ru) | 2012-04-10 |
| JP5480167B2 (ja) | 2014-04-23 |
| BRPI0906098B8 (pt) | 2018-02-27 |
| CO6290753A2 (es) | 2011-06-20 |
| ZA201005350B (en) | 2011-10-26 |
| CL2009000503A1 (es) | 2010-04-09 |
| CA2714409A1 (en) | 2009-09-11 |
| IL207526A (en) | 2014-06-30 |
| AR070803A1 (es) | 2010-05-05 |
| TW200940521A (en) | 2009-10-01 |
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