PL60562B1 - - Google Patents
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- Publication number
- PL60562B1 PL60562B1 PL113910A PL11391066A PL60562B1 PL 60562 B1 PL60562 B1 PL 60562B1 PL 113910 A PL113910 A PL 113910A PL 11391066 A PL11391066 A PL 11391066A PL 60562 B1 PL60562 B1 PL 60562B1
- Authority
- PL
- Poland
- Prior art keywords
- radical
- formula
- acid
- converted
- cyano
- Prior art date
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- -1 alkoxy radical Chemical class 0.000 claims description 22
- 150000001875 compounds Chemical class 0.000 claims description 22
- 150000003254 radicals Chemical class 0.000 claims description 19
- 238000000034 method Methods 0.000 claims description 15
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 12
- 238000002360 preparation method Methods 0.000 claims description 11
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 10
- 239000000047 product Substances 0.000 claims description 9
- 150000003839 salts Chemical class 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 6
- 150000001735 carboxylic acids Chemical class 0.000 claims description 5
- 239000007795 chemical reaction product Substances 0.000 claims description 5
- 125000004185 ester group Chemical group 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 229910052740 iodine Inorganic materials 0.000 claims description 4
- 125000003277 amino group Chemical group 0.000 claims description 3
- 238000006356 dehydrogenation reaction Methods 0.000 claims description 3
- 150000007524 organic acids Chemical group 0.000 claims description 3
- 150000003577 thiophenes Chemical class 0.000 claims description 3
- WZKSXHQDXQKIQJ-UHFFFAOYSA-N F[C](F)F Chemical compound F[C](F)F WZKSXHQDXQKIQJ-UHFFFAOYSA-N 0.000 claims description 2
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical group [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- GLQWRXYOTXRDNH-UHFFFAOYSA-N thiophen-2-amine Chemical class NC1=CC=CS1 GLQWRXYOTXRDNH-UHFFFAOYSA-N 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 33
- 238000002844 melting Methods 0.000 description 26
- 230000008018 melting Effects 0.000 description 26
- 238000000354 decomposition reaction Methods 0.000 description 25
- 239000000243 solution Substances 0.000 description 22
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 20
- 239000002253 acid Substances 0.000 description 17
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 239000002904 solvent Substances 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 9
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 7
- 239000011734 sodium Substances 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 5
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 5
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 5
- 150000002148 esters Chemical class 0.000 description 5
- 229910052708 sodium Inorganic materials 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 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 4
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 229910052938 sodium sulfate Inorganic materials 0.000 description 4
- 235000011152 sodium sulphate Nutrition 0.000 description 4
- JDMFXJULNGEPOI-UHFFFAOYSA-N 2,6-dichloroaniline Chemical compound NC1=C(Cl)C=CC=C1Cl JDMFXJULNGEPOI-UHFFFAOYSA-N 0.000 description 3
- PQEGEBSTPQVBSW-UHFFFAOYSA-N 3-(2,3-dimethylanilino)thiophene-2-carboxylic acid Chemical compound CC1=C(NC2=C(SC=C2)C(=O)O)C=CC=C1C PQEGEBSTPQVBSW-UHFFFAOYSA-N 0.000 description 3
- CWEUKXMDWMAICX-UHFFFAOYSA-N 4-(2,6-dichloroanilino)thiophene-3-carboxylic acid Chemical compound OC(=O)C1=CSC=C1NC1=C(Cl)C=CC=C1Cl CWEUKXMDWMAICX-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 229960000583 acetic acid Drugs 0.000 description 3
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 3
- 230000003110 anti-inflammatory effect Effects 0.000 description 3
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 239000012362 glacial acetic acid Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- UGNWTBMOAKPKBL-UHFFFAOYSA-N tetrachloro-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(Cl)=C(Cl)C1=O UGNWTBMOAKPKBL-UHFFFAOYSA-N 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 2
- DOLQYFPDPKPQSS-UHFFFAOYSA-N 3,4-dimethylaniline Chemical compound CC1=CC=C(N)C=C1C DOLQYFPDPKPQSS-UHFFFAOYSA-N 0.000 description 2
- VIUDTWATMPPKEL-UHFFFAOYSA-N 3-(trifluoromethyl)aniline Chemical compound NC1=CC=CC(C(F)(F)F)=C1 VIUDTWATMPPKEL-UHFFFAOYSA-N 0.000 description 2
- WXHIHVGMTKXUAU-UHFFFAOYSA-N 4-(2,3-dimethylanilino)thiophene-3-carbonitrile Chemical compound CC1=C(NC2=CSC=C2C#N)C=CC=C1C WXHIHVGMTKXUAU-UHFFFAOYSA-N 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- 101100037762 Caenorhabditis elegans rnh-2 gene Proteins 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 2
- 206010015150 Erythema Diseases 0.000 description 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 150000001448 anilines Chemical class 0.000 description 2
- 230000001754 anti-pyretic effect Effects 0.000 description 2
- 229960004365 benzoic acid Drugs 0.000 description 2
- 235000010233 benzoic acid Nutrition 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 230000020176 deacylation Effects 0.000 description 2
- 238000005947 deacylation reaction Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 231100000321 erythema Toxicity 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 239000011630 iodine Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- RUEWFRBGWGXUEM-UHFFFAOYSA-N methyl 4-(2,6-dichloroanilino)-5-methylthiophene-3-carboxylate Chemical compound COC(=O)C1=CSC(C)=C1NC1=C(Cl)C=CC=C1Cl RUEWFRBGWGXUEM-UHFFFAOYSA-N 0.000 description 2
- VSHTWPWTCXQLQN-UHFFFAOYSA-N n-butylaniline Chemical compound CCCCNC1=CC=CC=C1 VSHTWPWTCXQLQN-UHFFFAOYSA-N 0.000 description 2
- RNVCVTLRINQCPJ-UHFFFAOYSA-N o-toluidine Chemical compound CC1=CC=CC=C1N RNVCVTLRINQCPJ-UHFFFAOYSA-N 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 229960002895 phenylbutazone Drugs 0.000 description 2
- VYMDGNCVAMGZFE-UHFFFAOYSA-N phenylbutazonum Chemical compound O=C1C(CCCC)C(=O)N(C=2C=CC=CC=2)N1C1=CC=CC=C1 VYMDGNCVAMGZFE-UHFFFAOYSA-N 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 229930192474 thiophene Natural products 0.000 description 2
- CUPOOAWTRIURFT-UHFFFAOYSA-N thiophene-2-carbonitrile Chemical class N#CC1=CC=CS1 CUPOOAWTRIURFT-UHFFFAOYSA-N 0.000 description 2
- QERYCTSHXKAMIS-UHFFFAOYSA-N thiophene-2-carboxylic acid Chemical class OC(=O)C1=CC=CS1 QERYCTSHXKAMIS-UHFFFAOYSA-N 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- 231100000419 toxicity Toxicity 0.000 description 2
- 230000001988 toxicity Effects 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- FHMPFSKGDPKPDJ-UHFFFAOYSA-N 2,3,6-trimethylaniline Chemical compound CC1=CC=C(C)C(N)=C1C FHMPFSKGDPKPDJ-UHFFFAOYSA-N 0.000 description 1
- LEWZOBYWGWKNCK-UHFFFAOYSA-N 2,3-dihydro-1h-inden-5-amine Chemical compound NC1=CC=C2CCCC2=C1 LEWZOBYWGWKNCK-UHFFFAOYSA-N 0.000 description 1
- AYVZXDFCFQSWJD-UHFFFAOYSA-N 2,6-dichloro-3-methylaniline Chemical compound CC1=CC=C(Cl)C(N)=C1Cl AYVZXDFCFQSWJD-UHFFFAOYSA-N 0.000 description 1
- VBLXCTYLWZJBKA-UHFFFAOYSA-N 2-(trifluoromethyl)aniline Chemical compound NC1=CC=CC=C1C(F)(F)F VBLXCTYLWZJBKA-UHFFFAOYSA-N 0.000 description 1
- WFNLHDJJZSJARK-UHFFFAOYSA-N 2-chloro-6-methylaniline Chemical group CC1=CC=CC(Cl)=C1N WFNLHDJJZSJARK-UHFFFAOYSA-N 0.000 description 1
- YMDNODNLFSHHCV-UHFFFAOYSA-N 2-chloro-n,n-diethylethanamine Chemical compound CCN(CC)CCCl YMDNODNLFSHHCV-UHFFFAOYSA-N 0.000 description 1
- LGDHZCLREKIGKJ-UHFFFAOYSA-N 3,4-dimethoxyaniline Chemical compound COC1=CC=C(N)C=C1OC LGDHZCLREKIGKJ-UHFFFAOYSA-N 0.000 description 1
- PKSVGXWYIIJWGH-UHFFFAOYSA-N 3-(2,3-dichloroanilino)thiophene-2-carboxylic acid Chemical compound ClC1=C(NC2=C(SC=C2)C(=O)O)C=CC=C1Cl PKSVGXWYIIJWGH-UHFFFAOYSA-N 0.000 description 1
- SLWLIBFEBFJIMY-UHFFFAOYSA-N 3-(2,6-dichloroanilino)thiophene-2-carboxylic acid Chemical compound S1C=CC(NC=2C(=CC=CC=2Cl)Cl)=C1C(=O)O SLWLIBFEBFJIMY-UHFFFAOYSA-N 0.000 description 1
- FOSQFGVKHUAVNE-UHFFFAOYSA-N 3-(2,6-dimethylanilino)thiophene-2-carboxylic acid Chemical compound CC1=C(NC2=C(SC=C2)C(=O)O)C(=CC=C1)C FOSQFGVKHUAVNE-UHFFFAOYSA-N 0.000 description 1
- NNHXRUDOPLVTMS-UHFFFAOYSA-N 3-(2-chloroanilino)thiophene-2-carboxylic acid Chemical compound ClC1=C(NC2=C(SC=C2)C(=O)O)C=CC=C1 NNHXRUDOPLVTMS-UHFFFAOYSA-N 0.000 description 1
- ATANNAJKSFDCGR-UHFFFAOYSA-N 3-(2-phenylethoxy)aniline Chemical compound NC1=CC=CC(OCCC=2C=CC=CC=2)=C1 ATANNAJKSFDCGR-UHFFFAOYSA-N 0.000 description 1
- FJRYBTGNQFYGIW-UHFFFAOYSA-N 3-(3,4-dimethylanilino)thiophene-2-carboxylic acid Chemical compound CC=1C=C(NC2=C(SC=C2)C(=O)O)C=CC1C FJRYBTGNQFYGIW-UHFFFAOYSA-N 0.000 description 1
- YUGHWVNGFOVRSV-UHFFFAOYSA-N 3-(4-ethoxyanilino)thiophene-2-carboxylic acid Chemical compound C(C)OC1=CC=C(NC2=C(SC=C2)C(=O)O)C=C1 YUGHWVNGFOVRSV-UHFFFAOYSA-N 0.000 description 1
- VFKSCJTVSOGPCO-UHFFFAOYSA-N 3-(4-fluoroanilino)thiophene-2-carboxylic acid Chemical compound S1C=CC(NC=2C=CC(F)=CC=2)=C1C(=O)O VFKSCJTVSOGPCO-UHFFFAOYSA-N 0.000 description 1
- DPBDOUSDHLHDRA-UHFFFAOYSA-N 3-(4-propan-2-ylanilino)thiophene-2-carboxylic acid Chemical compound C(C)(C)C1=CC=C(NC2=C(SC=C2)C(=O)O)C=C1 DPBDOUSDHLHDRA-UHFFFAOYSA-N 0.000 description 1
- DTPVHHHYUHDVLY-UHFFFAOYSA-N 3-[2-(trifluoromethyl)anilino]thiophene-2-carboxylic acid Chemical compound S1C=CC(NC=2C(=CC=CC=2)C(F)(F)F)=C1C(=O)O DTPVHHHYUHDVLY-UHFFFAOYSA-N 0.000 description 1
- FRKPCXYPIHAOFI-UHFFFAOYSA-N 3-methylaniline Chemical compound [CH2]C1=CC=CC(N)=C1 FRKPCXYPIHAOFI-UHFFFAOYSA-N 0.000 description 1
- WYQDLENRCGHSPX-UHFFFAOYSA-N 4-(2,3-dichloroanilino)thiophene-3-carbonitrile Chemical compound ClC1=C(NC2=CSC=C2C#N)C=CC=C1Cl WYQDLENRCGHSPX-UHFFFAOYSA-N 0.000 description 1
- VBYQGFVYASOKSL-UHFFFAOYSA-N 4-(2,4,6-trimethylanilino)-2,5-dihydrothiophene-3-carbonitrile Chemical compound CC1=C(NC=2CSCC=2C#N)C(=CC(=C1)C)C VBYQGFVYASOKSL-UHFFFAOYSA-N 0.000 description 1
- WCYVGOMGUCKGFX-UHFFFAOYSA-N 4-(2,4-dichloro-5-methylanilino)thiophene-3-carbonitrile Chemical compound ClC1=C(NC2=CSC=C2C#N)C=C(C(=C1)Cl)C WCYVGOMGUCKGFX-UHFFFAOYSA-N 0.000 description 1
- SGGWYLXMEYVDOE-UHFFFAOYSA-N 4-(2,6-dichloroanilino)thiophene-3-carbonitrile Chemical compound ClC1=CC=CC(Cl)=C1NC1=CSC=C1C#N SGGWYLXMEYVDOE-UHFFFAOYSA-N 0.000 description 1
- VJIBENZYQWSMHS-UHFFFAOYSA-N 4-(2,6-dimethylanilino)thiophene-3-carbonitrile Chemical compound CC1=C(NC2=CSC=C2C#N)C(=CC=C1)C VJIBENZYQWSMHS-UHFFFAOYSA-N 0.000 description 1
- SBTOIPCXKHBWKA-UHFFFAOYSA-N 4-(2-chloro-3-methylanilino)-2,5-dihydrothiophene-3-carbonitrile Chemical compound ClC1=C(NC=2CSCC=2C#N)C=CC=C1C SBTOIPCXKHBWKA-UHFFFAOYSA-N 0.000 description 1
- MZZCNHHJVYCQRD-UHFFFAOYSA-N 4-(2-chloro-3-methylanilino)thiophene-3-carbonitrile Chemical compound ClC1=C(NC2=CSC=C2C#N)C=CC=C1C MZZCNHHJVYCQRD-UHFFFAOYSA-N 0.000 description 1
- MAGMHVGCLSZEIT-UHFFFAOYSA-N 4-(2-chloroanilino)thiophene-3-carbonitrile Chemical compound ClC1=C(NC2=CSC=C2C#N)C=CC=C1 MAGMHVGCLSZEIT-UHFFFAOYSA-N 0.000 description 1
- VEFUBIQEJIFCRQ-UHFFFAOYSA-N 4-(3,4-dimethylanilino)thiophene-3-carbonitrile Chemical compound CC=1C=C(NC2=CSC=C2C#N)C=CC=1C VEFUBIQEJIFCRQ-UHFFFAOYSA-N 0.000 description 1
- RBIIWWZZORODKE-UHFFFAOYSA-N 4-(4-ethoxyanilino)thiophene-3-carbonitrile Chemical compound C(C)OC1=CC=C(NC2=CSC=C2C#N)C=C1 RBIIWWZZORODKE-UHFFFAOYSA-N 0.000 description 1
- YTZRDPYRBNHGRR-UHFFFAOYSA-N 4-[3-(trifluoromethyl)anilino]-2,5-dihydrothiophene-3-carbonitrile Chemical compound FC(C=1C=C(NC=2CSCC2C#N)C=CC1)(F)F YTZRDPYRBNHGRR-UHFFFAOYSA-N 0.000 description 1
- LLSVPXMALQOPAA-UHFFFAOYSA-N 4-[3-(trifluoromethyl)anilino]thiophene-3-carbonitrile Chemical compound FC(C=1C=C(NC2=CSC=C2C#N)C=CC1)(F)F LLSVPXMALQOPAA-UHFFFAOYSA-N 0.000 description 1
- VQKAQKOHQUHGTN-UHFFFAOYSA-N 4-chloro-N,N-diethoxyaniline Chemical compound CCON(OCC)C1=CC=C(Cl)C=C1 VQKAQKOHQUHGTN-UHFFFAOYSA-N 0.000 description 1
- SLMYAIGAJWJBKI-UHFFFAOYSA-N 4-cyclohexyl-2-methylaniline Chemical compound C1=C(N)C(C)=CC(C2CCCCC2)=C1 SLMYAIGAJWJBKI-UHFFFAOYSA-N 0.000 description 1
- IMPPGHMHELILKG-UHFFFAOYSA-N 4-ethoxyaniline Chemical compound CCOC1=CC=C(N)C=C1 IMPPGHMHELILKG-UHFFFAOYSA-N 0.000 description 1
- ODGIMMLDVSWADK-UHFFFAOYSA-N 4-trifluoromethylaniline Chemical compound NC1=CC=C(C(F)(F)F)C=C1 ODGIMMLDVSWADK-UHFFFAOYSA-N 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- RMMXTBMQSGEXHJ-UHFFFAOYSA-N Aminophenazone Chemical compound O=C1C(N(C)C)=C(C)N(C)N1C1=CC=CC=C1 RMMXTBMQSGEXHJ-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- DJQVGQNLOQVRGF-UHFFFAOYSA-N C(C)(C)C1=CC=C(NC2=CSC=C2C#N)C=C1 Chemical compound C(C)(C)C1=CC=C(NC2=CSC=C2C#N)C=C1 DJQVGQNLOQVRGF-UHFFFAOYSA-N 0.000 description 1
- PGUODAXRIRBPAO-UHFFFAOYSA-N C1(CCCCC1)C1=CC=C(NC2=C(SC=C2)C(=O)O)C=C1 Chemical compound C1(CCCCC1)C1=CC=C(NC2=C(SC=C2)C(=O)O)C=C1 PGUODAXRIRBPAO-UHFFFAOYSA-N 0.000 description 1
- YDFAYSIZBKGBJD-UHFFFAOYSA-N C1(CCCCC1)C1=CC=C(NC2=CSC=C2C#N)C=C1 Chemical compound C1(CCCCC1)C1=CC=C(NC2=CSC=C2C#N)C=C1 YDFAYSIZBKGBJD-UHFFFAOYSA-N 0.000 description 1
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- HZJCAUPKLDBZPN-UHFFFAOYSA-M sodium;thiophene-3-carboxylate Chemical compound [Na+].[O-]C(=O)C=1C=CSC=1 HZJCAUPKLDBZPN-UHFFFAOYSA-M 0.000 description 1
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- GSXCEVHRIVLFJV-UHFFFAOYSA-N thiophene-3-carbonitrile Chemical class N#CC=1C=CSC=1 GSXCEVHRIVLFJV-UHFFFAOYSA-N 0.000 description 1
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PL60562B1 true PL60562B1 (cg-RX-API-DMAC7.html) | 1970-06-25 |
Family
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