NO832314L - Ditioforbindelser, farmasoeytiske preparater inneholdende dem samt deres anvendelse - Google Patents

Info

Publication number

NO832314L

NO832314L NO832314A NO832314A NO832314L NO 832314 L NO832314 L NO 832314L NO 832314 A NO832314 A NO 832314A NO 832314 A NO832314 A NO 832314A NO 832314 L NO832314 L NO 832314L

Authority

NO

Norway

Prior art keywords

lower alkyl

phenyl

formula

optionally substituted

halogen

Prior art date

1982-06-25

Links

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• 150000001875 compounds Chemical class 0.000 title claims description 247
• 239000000825 pharmaceutical preparation Substances 0.000 title description 13
• -1 ketene thioacetals Chemical class 0.000 claims description 610
• 125000000217 alkyl group Chemical group 0.000 claims description 489
• 125000003545 alkoxy group Chemical group 0.000 claims description 185
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 178
• 229910052736 halogen Inorganic materials 0.000 claims description 162
• 150000002367 halogens Chemical class 0.000 claims description 160
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 152
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 113
• 125000003282 alkyl amino group Chemical group 0.000 claims description 101
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 73
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 72
• 125000004434 sulfur atom Chemical group 0.000 claims description 72
• 238000000034 method Methods 0.000 claims description 66
• 125000002947 alkylene group Chemical group 0.000 claims description 65
• 239000000203 mixture Substances 0.000 claims description 64
• 150000003839 salts Chemical class 0.000 claims description 64
• 125000004432 carbon atom Chemical group C* 0.000 claims description 62
• 239000003795 chemical substances by application Substances 0.000 claims description 60
• 125000002252 acyl group Chemical group 0.000 claims description 57
• 229910052717 sulfur Inorganic materials 0.000 claims description 57
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 56
• 125000003118 aryl group Chemical group 0.000 claims description 52
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 52
• 125000004423 acyloxy group Chemical group 0.000 claims description 49
• 238000006243 chemical reaction Methods 0.000 claims description 49
• 239000007858 starting material Substances 0.000 claims description 49
• 125000005237 alkyleneamino group Chemical group 0.000 claims description 46
• 239000001257 hydrogen Substances 0.000 claims description 43
• 229910052739 hydrogen Inorganic materials 0.000 claims description 43
• 239000002253 acid Substances 0.000 claims description 42
• 125000005236 alkanoylamino group Chemical group 0.000 claims description 40
• 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 40
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 40
• 125000004430 oxygen atom Chemical group O* 0.000 claims description 40
• 125000004414 alkyl thio group Chemical group 0.000 claims description 39
• 125000001072 heteroaryl group Chemical group 0.000 claims description 37
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 37
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 36
• 238000002360 preparation method Methods 0.000 claims description 35
• 229910052799 carbon Inorganic materials 0.000 claims description 33
• 150000002430 hydrocarbons Chemical group 0.000 claims description 33
• QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 claims description 31
• 125000001931 aliphatic group Chemical group 0.000 claims description 31
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 30
• 229910052757 nitrogen Inorganic materials 0.000 claims description 30
• 229910052801 chlorine Inorganic materials 0.000 claims description 28
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 27
• 125000003342 alkenyl group Chemical group 0.000 claims description 27
• 150000001721 carbon Chemical group 0.000 claims description 27
• 239000000460 chlorine Substances 0.000 claims description 27
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 26
• 229910052731 fluorine Inorganic materials 0.000 claims description 26
• 239000011737 fluorine Substances 0.000 claims description 26
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 26
• 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 26
• 125000004076 pyridyl group Chemical group 0.000 claims description 25
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 24
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 24
• 229910052794 bromium Inorganic materials 0.000 claims description 24
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 23
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 22
• 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 21
• 150000002431 hydrogen Chemical group 0.000 claims description 20
• 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 19
• 125000003277 amino group Chemical group 0.000 claims description 19
• 229910052760 oxygen Inorganic materials 0.000 claims description 19
• 239000001301 oxygen Substances 0.000 claims description 19
• 125000001544 thienyl group Chemical group 0.000 claims description 19
• 125000003396 thiol group Chemical group [H]S* 0.000 claims description 19
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 18
• VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 17
• 239000005977 Ethylene Substances 0.000 claims description 17
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 17
• 125000002541 furyl group Chemical group 0.000 claims description 17
• 125000004043 oxo group Chemical group O=* 0.000 claims description 16
• 150000003254 radicals Chemical class 0.000 claims description 16
• MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 15
• 150000001450 anions Chemical class 0.000 claims description 15
• 125000001231 benzoyloxy group Chemical group C(C1=CC=CC=C1)(=O)O* 0.000 claims description 15
• 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 15
• 125000004450 alkenylene group Chemical group 0.000 claims description 14
• 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 14
• 229910052751 metal Inorganic materials 0.000 claims description 14
• 239000002184 metal Substances 0.000 claims description 14
• 230000008569 process Effects 0.000 claims description 14
• 125000005678 ethenylene group Chemical group [H]C([*:1])=C([H])[*:2] 0.000 claims description 13
• 125000000524 functional group Chemical group 0.000 claims description 13
• 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 13
• 238000012546 transfer Methods 0.000 claims description 13
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 12
• 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 11
• 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 11
• 238000004519 manufacturing process Methods 0.000 claims description 11
• CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical group [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 10
• 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 10
• 125000001118 alkylidene group Chemical group 0.000 claims description 10
• 125000005928 isopropyloxycarbonyl group Chemical group [H]C([H])([H])C([H])(OC(*)=O)C([H])([H])[H] 0.000 claims description 10
• 125000003441 thioacyl group Chemical group 0.000 claims description 10
• 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 9
• 125000002950 monocyclic group Chemical group 0.000 claims description 9
• 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 9
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 9
• 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 9
• 229920002554 vinyl polymer Polymers 0.000 claims description 9
• WGLLSSPDPJPLOR-UHFFFAOYSA-N 2,3-dimethylbut-2-ene Chemical group CC(C)=C(C)C WGLLSSPDPJPLOR-UHFFFAOYSA-N 0.000 claims description 8
• 239000002168 alkylating agent Substances 0.000 claims description 8
• 229940100198 alkylating agent Drugs 0.000 claims description 8
• 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 claims description 8
• 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 8
• 125000001624 naphthyl group Chemical group 0.000 claims description 8
• 125000003431 oxalo group Chemical group 0.000 claims description 8
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 7
• 150000001338 aliphatic hydrocarbons Chemical group 0.000 claims description 7
• 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 7
• 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 7
• 125000002883 imidazolyl group Chemical group 0.000 claims description 7
• 125000001041 indolyl group Chemical group 0.000 claims description 7
• 125000000842 isoxazolyl group Chemical group 0.000 claims description 7
• 125000002971 oxazolyl group Chemical group 0.000 claims description 7
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 7
• 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 7
• 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 6
• 125000006323 alkenyl amino group Chemical group 0.000 claims description 6
• 125000003302 alkenyloxy group Chemical group 0.000 claims description 6
• 125000005138 alkoxysulfonyl group Chemical group 0.000 claims description 6
• 125000000304 alkynyl group Chemical group 0.000 claims description 6
• 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 6
• 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 6
• 125000006222 dimethylaminomethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])* 0.000 claims description 6
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 6
• 238000007363 ring formation reaction Methods 0.000 claims description 6
• 125000003006 2-dimethylaminoethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims description 5
• 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 5
• 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 5
• 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims description 5
• 125000005517 carbenium group Chemical group 0.000 claims description 5
• 125000001841 imino group Chemical group [H]N=* 0.000 claims description 5
• 125000001064 morpholinomethyl group Chemical group [H]C([H])(*)N1C([H])([H])C([H])([H])OC([H])([H])C1([H])[H] 0.000 claims description 5
• 125000001038 naphthoyl group Chemical group C1(=CC=CC2=CC=CC=C12)C(=O)* 0.000 claims description 5
• 125000000335 thiazolyl group Chemical group 0.000 claims description 5
• GQQIOHKGLFZJDS-UHFFFAOYSA-N 1-methoxy-4-[2-(2-methylphenyl)ethynyl]benzene Chemical group C1=CC(OC)=CC=C1C#CC1=CC=CC=C1C GQQIOHKGLFZJDS-UHFFFAOYSA-N 0.000 claims description 4
• 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 4
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
• 239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 4
• 125000006263 dimethyl aminosulfonyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])S(*)(=O)=O 0.000 claims description 4
• CCGKOQOJPYTBIH-UHFFFAOYSA-N ethenone Chemical class C=C=O CCGKOQOJPYTBIH-UHFFFAOYSA-N 0.000 claims description 4
• 125000005843 halogen group Chemical group 0.000 claims description 4
• RIFHJAODNHLCBH-UHFFFAOYSA-N methanethione Chemical group S=[CH] RIFHJAODNHLCBH-UHFFFAOYSA-N 0.000 claims description 4
• JFGWPXKGINUNDH-UHFFFAOYSA-N methyl 3-phenylprop-2-ynoate Chemical group COC(=O)C#CC1=CC=CC=C1 JFGWPXKGINUNDH-UHFFFAOYSA-N 0.000 claims description 4
• 150000002825 nitriles Chemical class 0.000 claims description 4
• 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims description 4
• KJIZBVIKUWCBGU-UHFFFAOYSA-N octyl 2-(1,3-dithian-2-ylidene)-2-[3-(trifluoromethyl)phenyl]acetate Chemical compound C=1C=CC(C(F)(F)F)=CC=1C(C(=O)OCCCCCCCC)=C1SCCCS1 KJIZBVIKUWCBGU-UHFFFAOYSA-N 0.000 claims description 4
• 238000000926 separation method Methods 0.000 claims description 4
• SOKVHNRGXBDUAO-UHFFFAOYSA-N 2-[bis(4-fluorophenyl)methylidene]-1,3-dithiane Chemical compound C1=CC(F)=CC=C1C(C=1C=CC(F)=CC=1)=C1SCCCS1 SOKVHNRGXBDUAO-UHFFFAOYSA-N 0.000 claims description 3
• 125000003635 2-dimethylaminoethoxy group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])C([H])([H])O* 0.000 claims description 3
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
• XXTZHYXQVWRADW-UHFFFAOYSA-N diazomethanone Chemical compound [N]N=C=O XXTZHYXQVWRADW-UHFFFAOYSA-N 0.000 claims description 3
• 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 3
• 125000002312 hydrocarbylidene group Chemical group 0.000 claims description 3
• 230000003301 hydrolyzing effect Effects 0.000 claims description 3
• 238000006317 isomerization reaction Methods 0.000 claims description 3
• 125000005496 phosphonium group Chemical group 0.000 claims description 3
• VFXAZUNSZGDKCB-UHFFFAOYSA-N propan-2-yl 2-(1,3-dithiol-2-ylidene)-2-(4-fluorophenyl)acetate Chemical compound C=1C=C(F)C=CC=1C(C(=O)OC(C)C)=C1SC=CS1 VFXAZUNSZGDKCB-UHFFFAOYSA-N 0.000 claims description 3
• VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 claims description 3
• 150000003566 thiocarboxylic acids Chemical class 0.000 claims description 3
• MKGRNKFPGZXUKH-UHFFFAOYSA-N 2-[(3,4-dimethoxyphenyl)methylidene]-1,3-dithiolane Chemical compound C1=C(OC)C(OC)=CC=C1C=C1SCCS1 MKGRNKFPGZXUKH-UHFFFAOYSA-N 0.000 claims description 2
• NSEFTTRTTZOWRO-UHFFFAOYSA-N 2-[1-(1,3-dithian-2-ylidene)-2-phenylethyl]pyridine Chemical compound C=1C=CC=CC=1CC(C=1N=CC=CC=1)=C1SCCCS1 NSEFTTRTTZOWRO-UHFFFAOYSA-N 0.000 claims description 2
• VWFGHYLXNSRNGT-UHFFFAOYSA-N 2-[1-(4-fluorophenyl)ethylidene]-1,3-dithiolane Chemical compound C=1C=C(F)C=CC=1C(C)=C1SCCS1 VWFGHYLXNSRNGT-UHFFFAOYSA-N 0.000 claims description 2
• DPJXUVPWESDYLI-UHFFFAOYSA-N 4-[1,3-dithian-2-ylidene(phenyl)methyl]-n,n-dimethylaniline Chemical compound C1=CC(N(C)C)=CC=C1C(C=1C=CC=CC=1)=C1SCCCS1 DPJXUVPWESDYLI-UHFFFAOYSA-N 0.000 claims description 2
• 229910052782 aluminium Inorganic materials 0.000 claims description 2
• 125000005872 benzooxazolyl group Chemical group 0.000 claims description 2
• AEOCXXJPGCBFJA-UHFFFAOYSA-N ethionamide Chemical compound CCC1=CC(C(N)=S)=CC=N1 AEOCXXJPGCBFJA-UHFFFAOYSA-N 0.000 claims description 2
• KEHXBJVZKLLTQB-UHFFFAOYSA-N octyl 2-(1,3-dithiepan-2-ylidene)-2-[3-(trifluoromethyl)phenyl]acetate Chemical compound S1CCCCSC1=C(C(=O)OCCCCCCCC)C1=CC=CC(C(F)(F)F)=C1 KEHXBJVZKLLTQB-UHFFFAOYSA-N 0.000 claims description 2
• HDFRDWFLWVCOGP-UHFFFAOYSA-M sulfanylformate Chemical compound [O-]C(S)=O HDFRDWFLWVCOGP-UHFFFAOYSA-M 0.000 claims description 2
• 125000001589 carboacyl group Chemical group 0.000 claims 10
• XKDHDWOTKYRQQM-UHFFFAOYSA-N 2-(1,3-dithian-2-ylidene)-1-(4-methoxyphenyl)-2-[3-(trifluoromethyl)phenyl]ethanone Chemical compound C1=CC(OC)=CC=C1C(=O)C(C=1C=C(C=CC=1)C(F)(F)F)=C1SCCCS1 XKDHDWOTKYRQQM-UHFFFAOYSA-N 0.000 claims 1
• 239000005864 Sulphur Substances 0.000 claims 1
• IGOUYMHIMXMPDU-UHFFFAOYSA-N propan-2-yl 2-(1,3-dithiolan-2-ylidene)-2-(4-fluorophenyl)acetate Chemical compound C=1C=C(F)C=CC=1C(C(=O)OC(C)C)=C1SCCS1 IGOUYMHIMXMPDU-UHFFFAOYSA-N 0.000 claims 1
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 108
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 108
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 69
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 67
• 239000000243 solution Substances 0.000 description 63
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 60
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 57
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 48
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 48
• KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 47
• 239000002904 solvent Substances 0.000 description 46
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 44
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 39
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 39
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 37
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 35
• 239000002585 base Substances 0.000 description 34
• 239000000047 product Substances 0.000 description 30
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 29
• 239000012442 inert solvent Substances 0.000 description 29
• MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 28
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 26
• 229910052740 iodine Inorganic materials 0.000 description 25
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 24
• 229910052943 magnesium sulfate Inorganic materials 0.000 description 22
• 235000019341 magnesium sulphate Nutrition 0.000 description 22
• WEGYGNROSJDEIW-UHFFFAOYSA-N 3-Acetylpyridine Chemical compound CC(=O)C1=CC=CN=C1 WEGYGNROSJDEIW-UHFFFAOYSA-N 0.000 description 20
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 20
• 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 20
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 20
• 239000007864 aqueous solution Substances 0.000 description 19
• 238000004440 column chromatography Methods 0.000 description 18
• 239000003480 eluent Substances 0.000 description 18
• 125000001424 substituent group Chemical group 0.000 description 18
• JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 18
• HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Substances [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 17
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 17
• 229910052783 alkali metal Inorganic materials 0.000 description 16
• 229930195733 hydrocarbon Natural products 0.000 description 16
• 239000011261 inert gas Substances 0.000 description 16
• 239000004215 Carbon black (E152) Substances 0.000 description 15
• 241001465754 Metazoa Species 0.000 description 15
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 15
• 238000012360 testing method Methods 0.000 description 15
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