JPS59212477A - β−（ベンズチアゾリルチオ）−およびβ−（ベンズイミダゾリルチオ）−カルボン酸類の製造方法 - Google Patents
β−（ベンズチアゾリルチオ）−およびβ−（ベンズイミダゾリルチオ）−カルボン酸類の製造方法Info
- Publication number
- JPS59212477A JPS59212477A JP59094773A JP9477384A JPS59212477A JP S59212477 A JPS59212477 A JP S59212477A JP 59094773 A JP59094773 A JP 59094773A JP 9477384 A JP9477384 A JP 9477384A JP S59212477 A JPS59212477 A JP S59212477A
- Authority
- JP
- Japan
- Prior art keywords
- group
- acid
- formula
- hydrogen
- reaction
- 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.)
- Granted
Links
- 238000004519 manufacturing process Methods 0.000 title claims description 5
- 239000002253 acid Substances 0.000 claims description 36
- 238000006243 chemical reaction Methods 0.000 claims description 21
- 150000001875 compounds Chemical class 0.000 claims description 17
- 229910052739 hydrogen Inorganic materials 0.000 claims description 16
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 14
- 239000001257 hydrogen Substances 0.000 claims description 12
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 11
- 238000000034 method Methods 0.000 claims description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 10
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 claims description 9
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 9
- 150000008065 acid anhydrides Chemical class 0.000 claims description 8
- 150000002431 hydrogen Chemical class 0.000 claims description 8
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 7
- 230000002378 acidificating effect Effects 0.000 claims description 7
- 239000007864 aqueous solution Substances 0.000 claims description 7
- 239000012429 reaction media Substances 0.000 claims description 7
- 125000001188 haloalkyl group Chemical group 0.000 claims description 6
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 6
- 239000011976 maleic acid Substances 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 150000002367 halogens Chemical class 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- 125000001424 substituent group Chemical group 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 claims description 4
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 4
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 4
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- 125000005037 alkyl phenyl group Chemical group 0.000 claims description 3
- 125000004414 alkyl thio group Chemical group 0.000 claims description 3
- 125000002947 alkylene group Chemical group 0.000 claims description 3
- 150000008064 anhydrides Chemical class 0.000 claims description 3
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 3
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 3
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 3
- 125000003107 substituted aryl group Chemical group 0.000 claims description 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 2
- 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 150000003512 tertiary amines Chemical class 0.000 claims description 2
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 claims description 2
- 125000003277 amino group Chemical group 0.000 claims 1
- 125000004181 carboxyalkyl group Chemical group 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 125000002924 primary amino group Chemical class [H]N([H])* 0.000 claims 1
- 125000000467 secondary amino group Chemical class [H]N([*:1])[*:2] 0.000 claims 1
- YXIWHUQXZSMYRE-UHFFFAOYSA-N 1,3-benzothiazole-2-thiol Chemical compound C1=CC=C2SC(S)=NC2=C1 YXIWHUQXZSMYRE-UHFFFAOYSA-N 0.000 description 25
- -1 -No2 Chemical group 0.000 description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
- 239000000243 solution Substances 0.000 description 12
- 150000007513 acids Chemical class 0.000 description 11
- 229940054266 2-mercaptobenzothiazole Drugs 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- 238000003756 stirring Methods 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 8
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 8
- YHMYGUUIMTVXNW-UHFFFAOYSA-N 1,3-dihydrobenzimidazole-2-thione Chemical compound C1=CC=C2NC(S)=NC2=C1 YHMYGUUIMTVXNW-UHFFFAOYSA-N 0.000 description 7
- 125000004432 carbon atom Chemical group C* 0.000 description 7
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000002609 medium Substances 0.000 description 6
- 238000002844 melting Methods 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- 238000001953 recrystallisation Methods 0.000 description 5
- ZPOQJHGXQZVXIO-UHFFFAOYSA-N 3-(1,3-benzothiazol-2-yl)-4-oxo-4-sulfanylbutanoic acid Chemical compound C1=CC=C2SC(C(C(O)=S)CC(=O)O)=NC2=C1 ZPOQJHGXQZVXIO-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 150000001735 carboxylic acids Chemical class 0.000 description 4
- LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 4
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 239000002841 Lewis acid Substances 0.000 description 3
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 3
- 229960000583 acetic acid Drugs 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 239000001530 fumaric acid Substances 0.000 description 3
- 125000000623 heterocyclic group Chemical group 0.000 description 3
- 229910052500 inorganic mineral Inorganic materials 0.000 description 3
- 150000007517 lewis acids Chemical class 0.000 description 3
- 239000011707 mineral Substances 0.000 description 3
- 235000010755 mineral Nutrition 0.000 description 3
- 235000011121 sodium hydroxide Nutrition 0.000 description 3
- 229910052717 sulfur Inorganic materials 0.000 description 3
- XVOUMQNXTGKGMA-OWOJBTEDSA-N (E)-glutaconic acid Chemical compound OC(=O)C\C=C\C(O)=O XVOUMQNXTGKGMA-OWOJBTEDSA-N 0.000 description 2
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 description 2
- YYPNJNDODFVZLE-UHFFFAOYSA-N 3-methylbut-2-enoic acid Chemical compound CC(C)=CC(O)=O YYPNJNDODFVZLE-UHFFFAOYSA-N 0.000 description 2
- 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 2
- ZZIHEYOZBRPWMB-UHFFFAOYSA-N 5-chloro-1,3-dihydrobenzimidazole-2-thione Chemical compound ClC1=CC=C2NC(S)=NC2=C1 ZZIHEYOZBRPWMB-UHFFFAOYSA-N 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 2
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 239000012736 aqueous medium Substances 0.000 description 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 235000019253 formic acid Nutrition 0.000 description 2
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 238000001226 reprecipitation Methods 0.000 description 2
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 2
- 125000005023 xylyl group Chemical group 0.000 description 2
- NIONDZDPPYHYKY-SNAWJCMRSA-N (2E)-hexenoic acid Chemical compound CCC\C=C\C(O)=O NIONDZDPPYHYKY-SNAWJCMRSA-N 0.000 description 1
- CWMPPVPFLSZGCY-VOTSOKGWSA-N (2E)-oct-2-enoic acid Chemical compound CCCCC\C=C\C(O)=O CWMPPVPFLSZGCY-VOTSOKGWSA-N 0.000 description 1
- PAWGRNGPMLVJQH-UHFFFAOYSA-N (E)-2-Dodecenoic acid Natural products CCCCCCCCCC=CC(O)=O PAWGRNGPMLVJQH-UHFFFAOYSA-N 0.000 description 1
- 239000001124 (E)-prop-1-ene-1,2,3-tricarboxylic acid Substances 0.000 description 1
- UBJNPHAYKBNFOC-XNWCZRBMSA-N (e)-2-phenylbut-2-enoic acid Chemical compound C\C=C(\C(O)=O)C1=CC=CC=C1 UBJNPHAYKBNFOC-XNWCZRBMSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 1
- DKZRLCHWDNEKRH-UHFFFAOYSA-N 1-nonoxynonane Chemical compound CCCCCCCCCOCCCCCCCCC DKZRLCHWDNEKRH-UHFFFAOYSA-N 0.000 description 1
- ZRMKAMAPVMHSFW-UHFFFAOYSA-N 2-(1,3-benzothiazol-2-ylsulfanyl)propanoic acid Chemical compound C1=CC=C2SC(SC(C)C(O)=O)=NC2=C1 ZRMKAMAPVMHSFW-UHFFFAOYSA-N 0.000 description 1
- QWUHZSXWNAAZBZ-UHFFFAOYSA-N 2-(3-carboxy-1-oxo-1-sulfanylpropan-2-yl)-1,3-benzothiazole-5-carboxylic acid Chemical compound OC(=O)C1=CC=C2SC(C(C(O)=S)CC(=O)O)=NC2=C1 QWUHZSXWNAAZBZ-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- CWMPPVPFLSZGCY-UHFFFAOYSA-N 2-Octenoic Acid Natural products CCCCCC=CC(O)=O CWMPPVPFLSZGCY-UHFFFAOYSA-N 0.000 description 1
- KXTAOXNYQGASTA-UHFFFAOYSA-N 2-benzylidenepropanedioic acid Chemical compound OC(=O)C(C(O)=O)=CC1=CC=CC=C1 KXTAOXNYQGASTA-UHFFFAOYSA-N 0.000 description 1
- 125000000143 2-carboxyethyl group Chemical group [H]OC(=O)C([H])([H])C([H])([H])* 0.000 description 1
- HLUAPEYGTZFBLX-UHFFFAOYSA-N 2-ethylidenehexanedioic acid Chemical compound CC=C(C(O)=O)CCCC(O)=O HLUAPEYGTZFBLX-UHFFFAOYSA-N 0.000 description 1
- HSBSUGYTMJWPAX-UHFFFAOYSA-N 2-hexenedioic acid Chemical compound OC(=O)CCC=CC(O)=O HSBSUGYTMJWPAX-UHFFFAOYSA-N 0.000 description 1
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
- CWNNYYIZGGDCHS-UHFFFAOYSA-N 2-methylideneglutaric acid Chemical compound OC(=O)CCC(=C)C(O)=O CWNNYYIZGGDCHS-UHFFFAOYSA-N 0.000 description 1
- GQXRTXAQSDUAEY-UHFFFAOYSA-N 2-methylidenehexanedioic acid Chemical compound OC(=O)CCCC(=C)C(O)=O GQXRTXAQSDUAEY-UHFFFAOYSA-N 0.000 description 1
- ONPJWQSDZCGSQM-UHFFFAOYSA-N 2-phenylprop-2-enoic acid Chemical compound OC(=O)C(=C)C1=CC=CC=C1 ONPJWQSDZCGSQM-UHFFFAOYSA-N 0.000 description 1
- JJKFHPCWCOXSPU-UHFFFAOYSA-N 2-sulfanylidene-1,3-dihydrobenzimidazole-5-carbonitrile Chemical compound N#CC1=CC=C2NC(S)=NC2=C1 JJKFHPCWCOXSPU-UHFFFAOYSA-N 0.000 description 1
- DCRZVUIGGYMOBI-UHFFFAOYSA-N 2-sulfanylidene-1,3-dihydrobenzimidazole-5-carboxylic acid Chemical compound OC(=O)C1=CC=C2NC(=S)NC2=C1 DCRZVUIGGYMOBI-UHFFFAOYSA-N 0.000 description 1
- YDRKHDJUGAULIN-UHFFFAOYSA-N 2-sulfanylidene-3h-1,3-benzothiazole-5-carbonitrile Chemical compound N#CC1=CC=C2SC(S)=NC2=C1 YDRKHDJUGAULIN-UHFFFAOYSA-N 0.000 description 1
- SWFYMDYYCUPCQW-UHFFFAOYSA-N 2-sulfanylidene-3h-1,3-benzothiazole-5-carboxamide Chemical compound NC(=O)C1=CC=C2SC(S)=NC2=C1 SWFYMDYYCUPCQW-UHFFFAOYSA-N 0.000 description 1
- NLPZRWDNWKLLCI-UHFFFAOYSA-N 2-sulfanylidene-3h-1,3-benzothiazole-5-carboxylic acid Chemical compound OC(=O)C1=CC=C2SC(=S)NC2=C1 NLPZRWDNWKLLCI-UHFFFAOYSA-N 0.000 description 1
- WXBXVVIUZANZAU-UHFFFAOYSA-N 2E-decenoic acid Natural products CCCCCCCC=CC(O)=O WXBXVVIUZANZAU-UHFFFAOYSA-N 0.000 description 1
- AHRGBNQQXOAACA-UHFFFAOYSA-N 3-(1,3-benzothiazol-2-ylsulfanyl)pentanedioic acid Chemical compound C1=CC=C2SC(SC(CC(O)=O)CC(=O)O)=NC2=C1 AHRGBNQQXOAACA-UHFFFAOYSA-N 0.000 description 1
- GVIDXMLXAPYFLY-UHFFFAOYSA-N 3-(6-chloro-4-methyl-1,3-benzothiazol-2-yl)-4-oxo-4-sulfanylbutanoic acid Chemical compound CC1=CC(Cl)=CC2=C1N=C(C(CC(O)=O)C(O)=S)S2 GVIDXMLXAPYFLY-UHFFFAOYSA-N 0.000 description 1
- QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 description 1
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 description 1
- DWRWRXAXFHRUAC-UHFFFAOYSA-N 3-methylcyclohexene-1,2-dicarboxylic acid Chemical compound CC1CCCC(C(O)=O)=C1C(O)=O DWRWRXAXFHRUAC-UHFFFAOYSA-N 0.000 description 1
- AYKYXWQEBUNJCN-UHFFFAOYSA-N 3-methylfuran-2,5-dione Chemical compound CC1=CC(=O)OC1=O AYKYXWQEBUNJCN-UHFFFAOYSA-N 0.000 description 1
- OFNISBHGPNMTMS-UHFFFAOYSA-N 3-methylideneoxolane-2,5-dione Chemical compound C=C1CC(=O)OC1=O OFNISBHGPNMTMS-UHFFFAOYSA-N 0.000 description 1
- NTRIZZIJLMOQLR-UHFFFAOYSA-N 4-benzyl-1,3-dihydrobenzimidazole-2-thione Chemical compound C1=CC=C2NC(S)=NC2=C1CC1=CC=CC=C1 NTRIZZIJLMOQLR-UHFFFAOYSA-N 0.000 description 1
- CSDBFIYGLRXUDX-UHFFFAOYSA-N 4-fluoro-1,3-dihydrobenzimidazole-2-thione Chemical compound FC1=CC=CC2=C1N=C(S)N2 CSDBFIYGLRXUDX-UHFFFAOYSA-N 0.000 description 1
- RCIYHBWAAXQWTQ-UHFFFAOYSA-N 4-fluoro-3h-1,3-benzothiazole-2-thione Chemical compound FC1=CC=CC2=C1N=C(S)S2 RCIYHBWAAXQWTQ-UHFFFAOYSA-N 0.000 description 1
- 125000004176 4-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1F)C([H])([H])* 0.000 description 1
- KOBTUCRWSZGEKO-UHFFFAOYSA-N 4-hydroxy-1,3-dihydrobenzimidazole-2-thione Chemical compound OC1=CC=CC2=C1N=C(S)N2 KOBTUCRWSZGEKO-UHFFFAOYSA-N 0.000 description 1
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 125000006181 4-methyl benzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])C([H])([H])* 0.000 description 1
- FODDJZLXUBUTCG-UHFFFAOYSA-N 4-methylsulfanyl-3h-1,3-benzothiazole-2-thione Chemical compound CSC1=CC=CC2=C1N=C(S)S2 FODDJZLXUBUTCG-UHFFFAOYSA-N 0.000 description 1
- LYSPITZTNMFQBM-UHFFFAOYSA-N 4-phenyl-1,3-dihydrobenzimidazole-2-thione Chemical compound C=12NC(S)=NC2=CC=CC=1C1=CC=CC=C1 LYSPITZTNMFQBM-UHFFFAOYSA-N 0.000 description 1
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- SCBUQIQXUBOQAI-UHFFFAOYSA-N 4-phenylbut-2-enoic acid Chemical compound OC(=O)C=CCC1=CC=CC=C1 SCBUQIQXUBOQAI-UHFFFAOYSA-N 0.000 description 1
- GMVNKSKUBXRRLL-UHFFFAOYSA-N 4-propan-2-yl-1,3-dihydrobenzimidazole-2-thione Chemical compound CC(C)C1=CC=CC2=C1NC(S)=N2 GMVNKSKUBXRRLL-UHFFFAOYSA-N 0.000 description 1
- JDOYPEBMMLVKHE-UHFFFAOYSA-N 4-propan-2-yl-3h-1,3-benzothiazole-2-thione Chemical compound CC(C)C1=CC=CC2=C1N=C(S)S2 JDOYPEBMMLVKHE-UHFFFAOYSA-N 0.000 description 1
- JHNQFHYZWGYNKZ-UHFFFAOYSA-N 5-(2,4,4-trimethylpentan-2-yl)-1,3-dihydrobenzimidazole-2-thione Chemical compound CC(C)(C)CC(C)(C)C1=CC=C2NC(S)=NC2=C1 JHNQFHYZWGYNKZ-UHFFFAOYSA-N 0.000 description 1
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- CWIYBOJLSWJGKV-UHFFFAOYSA-N 5-methyl-1,3-dihydrobenzimidazole-2-thione Chemical compound CC1=CC=C2NC(S)=NC2=C1 CWIYBOJLSWJGKV-UHFFFAOYSA-N 0.000 description 1
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- YPXQSGWOGQPLQO-UHFFFAOYSA-N 5-nitro-1,3-dihydrobenzimidazole-2-thione Chemical compound [O-][N+](=O)C1=CC=C2N=C(S)NC2=C1 YPXQSGWOGQPLQO-UHFFFAOYSA-N 0.000 description 1
- IDPNFKLUBIKHSW-UHFFFAOYSA-N 6-amino-3h-1,3-benzothiazole-2-thione Chemical compound NC1=CC=C2N=C(S)SC2=C1 IDPNFKLUBIKHSW-UHFFFAOYSA-N 0.000 description 1
- UXZYGYFEKNAWDV-UHFFFAOYSA-N 6-butyl-5-chloro-3h-1,3-benzothiazole-2-thione Chemical compound C1=C(Cl)C(CCCC)=CC2=C1N=C(S)S2 UXZYGYFEKNAWDV-UHFFFAOYSA-N 0.000 description 1
- CLHLOHAQAADLRA-UHFFFAOYSA-N 6-chloro-3h-1,3-benzothiazole-2-thione Chemical compound C1=C(Cl)C=C2SC(S)=NC2=C1 CLHLOHAQAADLRA-UHFFFAOYSA-N 0.000 description 1
- HRIUCIMVVPGVKM-UHFFFAOYSA-N 6-chloro-4-methyl-3h-1,3-benzothiazole-2-thione Chemical compound CC1=CC(Cl)=CC2=C1NC(=S)S2 HRIUCIMVVPGVKM-UHFFFAOYSA-N 0.000 description 1
- ROPAWMWQGYCNCW-UHFFFAOYSA-N 6-cyclohexyl-3h-1,3-benzothiazole-2-thione Chemical compound C1=C2SC(S)=NC2=CC=C1C1CCCCC1 ROPAWMWQGYCNCW-UHFFFAOYSA-N 0.000 description 1
- YBSMSNSADXVROP-UHFFFAOYSA-N 6-methylsulfonyl-3h-1,3-benzothiazole-2-thione Chemical compound CS(=O)(=O)C1=CC=C2N=C(S)SC2=C1 YBSMSNSADXVROP-UHFFFAOYSA-N 0.000 description 1
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- YWXNRYBRNJLDHM-UHFFFAOYSA-N 6-propoxy-3h-1,3-benzothiazole-2-thione Chemical compound CCCOC1=CC=C2NC(=S)SC2=C1 YWXNRYBRNJLDHM-UHFFFAOYSA-N 0.000 description 1
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- ADJUCSVIOHCBNT-UHFFFAOYSA-N 7-hydroxy-3h-1,3-benzothiazole-2-thione Chemical compound OC1=CC=CC2=C1SC(S)=N2 ADJUCSVIOHCBNT-UHFFFAOYSA-N 0.000 description 1
- 229910021630 Antimony pentafluoride Inorganic materials 0.000 description 1
- PMVSDNDAUGGCCE-TYYBGVCCSA-L Ferrous fumarate Chemical compound [Fe+2].[O-]C(=O)\C=C\C([O-])=O PMVSDNDAUGGCCE-TYYBGVCCSA-L 0.000 description 1
- 240000007594 Oryza sativa Species 0.000 description 1
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- PQLAYKMGZDUDLQ-UHFFFAOYSA-K aluminium bromide Chemical compound Br[Al](Br)Br PQLAYKMGZDUDLQ-UHFFFAOYSA-K 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- VBVBHWZYQGJZLR-UHFFFAOYSA-I antimony pentafluoride Chemical compound F[Sb](F)(F)(F)F VBVBHWZYQGJZLR-UHFFFAOYSA-I 0.000 description 1
- 239000011260 aqueous acid Substances 0.000 description 1
- 239000002152 aqueous-organic solution Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 1
- 125000005997 bromomethyl group Chemical group 0.000 description 1
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 1
- 125000004744 butyloxycarbonyl group Chemical group 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- GTZCVFVGUGFEME-IWQZZHSRSA-N cis-aconitic acid Chemical compound OC(=O)C\C(C(O)=O)=C\C(O)=O GTZCVFVGUGFEME-IWQZZHSRSA-N 0.000 description 1
- HNEGQIOMVPPMNR-IHWYPQMZSA-N citraconic acid Chemical compound OC(=O)C(/C)=C\C(O)=O HNEGQIOMVPPMNR-IHWYPQMZSA-N 0.000 description 1
- 229940018557 citraconic acid Drugs 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 150000004683 dihydrates Chemical class 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 125000006182 dimethyl benzyl group Chemical group 0.000 description 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
- 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 description 1
- AIJZIRPGCQPZSL-UHFFFAOYSA-N ethylenetetracarboxylic acid Chemical compound OC(=O)C(C(O)=O)=C(C(O)=O)C(O)=O AIJZIRPGCQPZSL-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 229940093915 gynecological organic acid Drugs 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- HNEGQIOMVPPMNR-NSCUHMNNSA-N mesaconic acid Chemical compound OC(=O)C(/C)=C/C(O)=O HNEGQIOMVPPMNR-NSCUHMNNSA-N 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- DCUFMVPCXCSVNP-UHFFFAOYSA-N methacrylic anhydride Chemical compound CC(=C)C(=O)OC(=O)C(C)=C DCUFMVPCXCSVNP-UHFFFAOYSA-N 0.000 description 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
- RODLEVQAZWKRIQ-UHFFFAOYSA-N methyl 2-sulfanylidene-3h-1,3-benzothiazole-5-carboxylate Chemical compound COC(=O)C1=CC=C2SC(S)=NC2=C1 RODLEVQAZWKRIQ-UHFFFAOYSA-N 0.000 description 1
- HNEGQIOMVPPMNR-UHFFFAOYSA-N methylfumaric acid Natural products OC(=O)C(C)=CC(O)=O HNEGQIOMVPPMNR-UHFFFAOYSA-N 0.000 description 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
- 150000002763 monocarboxylic acids Chemical class 0.000 description 1
- 239000004570 mortar (masonry) Substances 0.000 description 1
- JJMCCZLIAMHGME-UHFFFAOYSA-N n-(2-imidazol-1-yl-2-phenylethyl)-1h-imidazole-5-carboxamide Chemical compound C=1N=CNC=1C(=O)NCC(N1C=NC=C1)C1=CC=CC=C1 JJMCCZLIAMHGME-UHFFFAOYSA-N 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 1
- XNERWVPQCYSMLC-UHFFFAOYSA-N phenylpropiolic acid Chemical compound OC(=O)C#CC1=CC=CC=C1 XNERWVPQCYSMLC-UHFFFAOYSA-N 0.000 description 1
- 229920000137 polyphosphoric acid Polymers 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- ARJOQCYCJMAIFR-UHFFFAOYSA-N prop-2-enoyl prop-2-enoate Chemical compound C=CC(=O)OC(=O)C=C ARJOQCYCJMAIFR-UHFFFAOYSA-N 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- UORVCLMRJXCDCP-UHFFFAOYSA-N propynoic acid Chemical compound OC(=O)C#C UORVCLMRJXCDCP-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 239000013049 sediment Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- UIIMBOGNXHQVGW-UHFFFAOYSA-N sodium;hydron;carbonate Chemical compound [Na+].OC(O)=O UIIMBOGNXHQVGW-UHFFFAOYSA-N 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- WXBXVVIUZANZAU-CMDGGOBGSA-N trans-2-decenoic acid Chemical compound CCCCCCC\C=C\C(O)=O WXBXVVIUZANZAU-CMDGGOBGSA-N 0.000 description 1
- PAWGRNGPMLVJQH-ZHACJKMWSA-N trans-2-dodecenoic acid Chemical compound CCCCCCCCC\C=C\C(O)=O PAWGRNGPMLVJQH-ZHACJKMWSA-N 0.000 description 1
- GTZCVFVGUGFEME-UHFFFAOYSA-N trans-aconitic acid Natural products OC(=O)CC(C(O)=O)=CC(O)=O GTZCVFVGUGFEME-UHFFFAOYSA-N 0.000 description 1
- LKOVPWSSZFDYPG-WUKNDPDISA-N trans-octadec-2-enoic acid Chemical compound CCCCCCCCCCCCCCC\C=C\C(O)=O LKOVPWSSZFDYPG-WUKNDPDISA-N 0.000 description 1
- YIYBQIKDCADOSF-ONEGZZNKSA-N trans-pent-2-enoic acid Chemical compound CC\C=C\C(O)=O YIYBQIKDCADOSF-ONEGZZNKSA-N 0.000 description 1
- IGBBVTAVILYDIO-MDZDMXLPSA-N trans-undec-2-enoic acid Chemical compound CCCCCCCC\C=C\C(O)=O IGBBVTAVILYDIO-MDZDMXLPSA-N 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
- C09D5/08—Anti-corrosive paints
- C09D5/082—Anti-corrosive paints characterised by the anti-corrosive pigment
- C09D5/086—Organic or non-macromolecular compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D233/28—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
- C07D277/62—Benzothiazoles
- C07D277/68—Benzothiazoles 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 in position 2
- C07D277/70—Sulfur atoms
- C07D277/74—Sulfur atoms substituted by carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Indole Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB8313321 | 1983-05-14 | ||
| GB838313321A GB8313321D0 (en) | 1983-05-14 | 1983-05-14 | Preparation of mercaptan substituted carboxylic acids |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS59212477A true JPS59212477A (ja) | 1984-12-01 |
| JPH053464B2 JPH053464B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1993-01-14 |
Family
ID=10542740
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP59094773A Granted JPS59212477A (ja) | 1983-05-14 | 1984-05-14 | β−（ベンズチアゾリルチオ）−およびβ−（ベンズイミダゾリルチオ）−カルボン酸類の製造方法 |
Country Status (7)
Families Citing this family (55)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8313322D0 (en) * | 1983-05-14 | 1983-06-22 | Ciba Geigy Ag | Heterocyclic-(cyclo)aliphatic carboxylic acids |
| DE3341633A1 (de) * | 1983-11-17 | 1985-05-30 | Sanshin Kagaku Kogyo Co., Ltd., Yanai, Yamaguchi | Rosthemmende substanz |
| GB8412063D0 (en) * | 1984-05-11 | 1984-06-20 | Ciba Geigy Ag | Compositions containing heterocyclic corrosion inhibitors |
| GB8412065D0 (en) * | 1984-05-11 | 1984-06-20 | Ciba Geigy Ag | Preparation of carboxylic acid derivatives |
| IT1185511B (it) * | 1985-02-19 | 1987-11-12 | Hoechst Italia | Agenti anticorrosivi acquosi contenenti un sale ammonico dell'acido 2-benzotiazoliltiocarbossilico |
| HU193951B (en) * | 1985-03-11 | 1987-12-28 | Richter Gedeon Vegyeszet | Process for producing new sulfur-containing 5-substituted benzimidazol derivatives and pharmaceutical compositions containing them |
| US5243047A (en) * | 1988-02-15 | 1993-09-07 | Imperial Chemical Industries Plc | Triazole/thiazole amino-s-triazine bonding agents |
| GB2290789B (en) * | 1994-07-01 | 1998-09-16 | Ciba Geigy Ag | Titanium and zirconium complexes of carboxylic acids as corrosion inhibitors |
| US6083416A (en) * | 1996-07-18 | 2000-07-04 | Fmc Corporation | Corrosion inhibiting processes for refrigeration systems |
| FR2765595B1 (fr) * | 1997-07-01 | 1999-10-01 | Lorraine Laminage | Composition pour protection temporaire contre la corrosion de pieces metalliques, ses procedes de preparation et d'application et pieces metalliques obtenues a partir de cette composition |
| US6004476A (en) * | 1997-07-26 | 1999-12-21 | Fmc Corporation | Corrosion inhibiting solutions and processes for refrigeration systems comprising heteropoly complex anions of transition metal elements additional additives |
| US6024892A (en) * | 1997-10-06 | 2000-02-15 | Fmc Corporation | Anticorrosion and pH stable alkali metal halide solutions for air dehumidification |
| US6326384B1 (en) | 1999-08-26 | 2001-12-04 | Robert R. Whittle | Dry blend pharmaceutical unit dosage form |
| US6780880B1 (en) | 1999-08-26 | 2004-08-24 | Robert R. Whittle | FT-Raman spectroscopic measurement |
| US6268385B1 (en) | 1999-08-26 | 2001-07-31 | Robert R. Whittle | Dry blend pharmaceutical formulations |
| US6312712B1 (en) | 1999-08-26 | 2001-11-06 | Robert R. Whittle | Method of improving bioavailability |
| US6369087B1 (en) | 1999-08-26 | 2002-04-09 | Robert R. Whittle | Alkoxy substituted benzimidazole compounds, pharmaceutical preparations containing the same, and methods of using the same |
| US6262085B1 (en) | 1999-08-26 | 2001-07-17 | Robert R. Whittle | Alkoxy substituted Benzimidazole compounds, pharmaceutical preparations containing the same, and methods of using the same |
| US6262086B1 (en) | 1999-08-26 | 2001-07-17 | Robert R. Whittle | Pharmaceutical unit dosage form |
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| RU2673338C1 (ru) * | 2017-11-29 | 2018-11-26 | Федеральное государственное бюджетное образовательное учреждение высшего образования "Санкт-Петербургский государственный химико-фармацевтический университет" Министерства здравоохранения Российской Федерации (ФГБОУ ВО СПХФУ Минздрава России) | Антигипоксическое и актопротекторное средство на основе 2-(этилсульфанил)-1Н-бензимидазол-3-ия (2Е)-3-карбоксипроп-2-еноата |
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Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2725364A (en) * | 1952-12-31 | 1955-11-29 | Monsanto Chemicals | Vinyl halide polymers plasticized with diesters of acid derivatives of 2-benzothiazolyl mercaptan |
| BE578934A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1958-05-23 | |||
| US3136689A (en) * | 1959-12-28 | 1964-06-09 | Monsanto Co | Heterocyclic esters effective against micro-organisms |
| SU149785A1 (ru) * | 1961-12-11 | 1962-11-30 | В.Г. Песин | Способ получени 2, 1, З-тиодиазол-4, 5-дикарбоновой кислоты |
| DE1542886A1 (de) * | 1966-10-04 | 1970-05-14 | Bayer Ag | Fungizide Mittel |
| BR7903775A (pt) * | 1978-06-15 | 1980-02-05 | Monsanto Co | Processo para regular o crescimento de plantas leguminosas,e composicao para uso no mesmo |
| US4289886A (en) * | 1979-07-05 | 1981-09-15 | Monsanto Company | Imides derived from 2-thioxo-3-benzox(thia)azoline acetic, and propionic acids |
| JPS58204183A (ja) * | 1982-05-22 | 1983-11-28 | Sanshin Kagaku Kogyo Kk | 防錆剤 |
-
1983
- 1983-05-14 GB GB838313321A patent/GB8313321D0/en active Pending
-
1984
- 1984-05-08 EP EP84810219A patent/EP0126030A3/de not_active Withdrawn
- 1984-05-11 SU SU843741050A patent/SU1277890A3/ru active
- 1984-05-12 ES ES532470A patent/ES8602692A1/es not_active Expired
- 1984-05-14 JP JP59094773A patent/JPS59212477A/ja active Granted
- 1984-05-14 US US06/610,145 patent/US4612378A/en not_active Expired - Lifetime
- 1984-11-14 BR BR8402250A patent/BR8402250A/pt not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| ES532470A0 (es) | 1985-12-16 |
| EP0126030A3 (de) | 1987-04-15 |
| EP0126030A2 (de) | 1984-11-21 |
| SU1277890A3 (ru) | 1986-12-15 |
| BR8402250A (pt) | 1984-12-18 |
| GB8313321D0 (en) | 1983-06-22 |
| JPH053464B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1993-01-14 |
| US4612378A (en) | 1986-09-16 |
| ES8602692A1 (es) | 1985-12-16 |
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