NO752888L

NO752888L -

Info

Publication number: NO752888L
Authority: NO; Norway
Prior art keywords: melting point; methyl; acid addition; hydrogen; lower alkyl
Prior art date: 1973-12-21

Application number

NO752888A

Other languages

English (en)

Norwegian (no)

Inventor

H Ramuz

Original Assignee

Hoffmann La Roche

Priority date

1973-12-21

Filing date

1975-08-20

Publication date

1975-06-24

1973-12-21 Priority claimed from CH1803073A external-priority patent/CH611614A5/xx

1975-06-24 Publication of NO752888L publication Critical patent/NO752888L/no

1975-08-20 Application filed by Hoffmann La Roche filed Critical Hoffmann La Roche

1975-08-20 Priority to NO752888A priority Critical patent/NO752888L/no

Links

150000001875 compounds Chemical class 0.000 claims description 112
-1 nitro, amino Chemical group 0.000 claims description 47
239000002253 acid Substances 0.000 claims description 32
150000003839 salts Chemical class 0.000 claims description 26
125000003545 alkoxy group Chemical group 0.000 claims description 24
239000001257 hydrogen Substances 0.000 claims description 23
229910052739 hydrogen Inorganic materials 0.000 claims description 23
125000000217 alkyl group Chemical group 0.000 claims description 19
125000004432 carbon atom Chemical group C* 0.000 claims description 16
229910052717 sulfur Inorganic materials 0.000 claims description 16
125000004434 sulfur atom Chemical group 0.000 claims description 15
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 14
229910052736 halogen Inorganic materials 0.000 claims description 11
150000002367 halogens Chemical class 0.000 claims description 11
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 8
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 8
150000002431 hydrogen Chemical class 0.000 claims description 8
125000001931 aliphatic group Chemical group 0.000 claims description 6
125000004414 alkyl thio group Chemical group 0.000 claims description 6
125000004093 cyano group Chemical group *C#N 0.000 claims description 6
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 6
125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 5
125000001589 carboacyl group Chemical group 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
125000004423 acyloxy group Chemical group 0.000 claims description 4
125000005236 alkanoylamino group Chemical group 0.000 claims description 4
125000003282 alkyl amino group Chemical group 0.000 claims description 4
125000005153 alkyl sulfamoyl group Chemical group 0.000 claims description 4
125000003368 amide group Chemical group 0.000 claims description 4
125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 4
125000004104 aryloxy group Chemical group 0.000 claims description 4
125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 4
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
ZROUQTNYPCANTN-UHFFFAOYSA-N Tiapamil Chemical compound C1=C(OC)C(OC)=CC=C1CCN(C)CCCC1(C=2C=C(OC)C(OC)=CC=2)S(=O)(=O)CCCS1(=O)=O ZROUQTNYPCANTN-UHFFFAOYSA-N 0.000 claims description 3
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 3
125000005195 alkyl amino carbonyloxy group Chemical group 0.000 claims description 3
239000000825 pharmaceutical preparation Substances 0.000 claims description 3
239000000463 material Substances 0.000 claims description 2
125000004356 hydroxy functional group Chemical group O* 0.000 claims 6
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 3
KYARBIJYVGJZLB-UHFFFAOYSA-N 7-amino-4-hydroxy-2-naphthalenesulfonic acid Chemical compound OC1=CC(S(O)(=O)=O)=CC2=CC(N)=CC=C21 KYARBIJYVGJZLB-UHFFFAOYSA-N 0.000 claims 1
239000003937 drug carrier Substances 0.000 claims 1
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 141
238000002844 melting Methods 0.000 description 122
230000008018 melting Effects 0.000 description 122
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 71
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 57
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 56
238000006243 chemical reaction Methods 0.000 description 43
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 39
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 39
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 36
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 36
239000000243 solution Substances 0.000 description 36
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 33
239000000203 mixture Substances 0.000 description 29
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 28
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 28
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 27
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 27
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 26
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 22
239000000284 extract Substances 0.000 description 19
HNJWKRMESUMDQE-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-n-methylethanamine Chemical compound CNCCC1=CC=C(OC)C(OC)=C1 HNJWKRMESUMDQE-UHFFFAOYSA-N 0.000 description 18
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 18
XEKOWRVHYACXOJ-UHFFFAOYSA-N ethyl acetate Substances CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
239000002904 solvent Substances 0.000 description 18
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 17
239000007858 starting material Substances 0.000 description 17
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 16
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 14
239000002585 base Substances 0.000 description 14
229910052943 magnesium sulfate Inorganic materials 0.000 description 14
235000019341 magnesium sulphate Nutrition 0.000 description 14
230000009467 reduction Effects 0.000 description 14
238000006722 reduction reaction Methods 0.000 description 14
238000010992 reflux Methods 0.000 description 14
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 12
KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 12
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
239000003960 organic solvent Substances 0.000 description 12
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 11
229910000041 hydrogen chloride Inorganic materials 0.000 description 11
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 10
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
229960000583 acetic acid Drugs 0.000 description 10
238000001704 evaporation Methods 0.000 description 10
230000008020 evaporation Effects 0.000 description 10
239000003921 oil Substances 0.000 description 10
235000019198 oils Nutrition 0.000 description 10
239000011541 reaction mixture Substances 0.000 description 9
235000011121 sodium hydroxide Nutrition 0.000 description 9
239000000725 suspension Substances 0.000 description 9
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
229910052783 alkali metal Inorganic materials 0.000 description 8
238000004458 analytical method Methods 0.000 description 8
229910052786 argon Inorganic materials 0.000 description 8
239000012362 glacial acetic acid Substances 0.000 description 8
230000003647 oxidation Effects 0.000 description 8
238000007254 oxidation reaction Methods 0.000 description 8
239000002244 precipitate Substances 0.000 description 8
ZJLMKPKYJBQJNH-UHFFFAOYSA-N propane-1,3-dithiol Chemical compound SCCCS ZJLMKPKYJBQJNH-UHFFFAOYSA-N 0.000 description 8
239000000741 silica gel Substances 0.000 description 8
229910002027 silica gel Inorganic materials 0.000 description 8
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 7
238000000354 decomposition reaction Methods 0.000 description 7
238000002360 preparation method Methods 0.000 description 7
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 6
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 6
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 6
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
PQLVXDKIJBQVDF-UHFFFAOYSA-N acetic acid;hydrate Chemical compound O.CC(O)=O PQLVXDKIJBQVDF-UHFFFAOYSA-N 0.000 description 6
150000001412 amines Chemical class 0.000 description 6
125000002887 hydroxy group Chemical group [H]O* 0.000 description 6
239000012280 lithium aluminium hydride Substances 0.000 description 6
238000000034 method Methods 0.000 description 6
BYSFFOIEDQTZBD-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-1,3-dithiane Chemical compound C1=C(OC)C(OC)=CC=C1C1SCCCS1 BYSFFOIEDQTZBD-UHFFFAOYSA-N 0.000 description 5
ODNGPQOKPLSWSJ-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-1,3-dithiane 1,1,3,3-tetraoxide Chemical compound C1=C(OC)C(OC)=CC=C1C1S(=O)(=O)CCCS1(=O)=O ODNGPQOKPLSWSJ-UHFFFAOYSA-N 0.000 description 5
GXKPARDRBFURON-UHFFFAOYSA-N 2-phenyl-1,3-dithiane Chemical compound S1CCCSC1C1=CC=CC=C1 GXKPARDRBFURON-UHFFFAOYSA-N 0.000 description 5
HJBBKVHYQQUPQW-UHFFFAOYSA-N 3-chloro-n-[2-(3,4-dimethoxyphenyl)ethyl]-n-methylpropan-1-amine Chemical compound COC1=CC=C(CCN(C)CCCCl)C=C1OC HJBBKVHYQQUPQW-UHFFFAOYSA-N 0.000 description 5
NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 5
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 5
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 5
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 5
238000009835 boiling Methods 0.000 description 5
239000003795 chemical substances by application Substances 0.000 description 5
150000004820 halides Chemical class 0.000 description 5
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 5
NIQQIJXGUZVEBB-UHFFFAOYSA-N methanol;propan-2-one Chemical compound OC.CC(C)=O NIQQIJXGUZVEBB-UHFFFAOYSA-N 0.000 description 5
239000000047 product Substances 0.000 description 5
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
229910052708 sodium Inorganic materials 0.000 description 5
239000011734 sodium Substances 0.000 description 5
239000012312 sodium hydride Substances 0.000 description 5
229910000104 sodium hydride Inorganic materials 0.000 description 5
238000003756 stirring Methods 0.000 description 5
YOIBGXUIAJFDER-UHFFFAOYSA-N 4-chloro-3,4-dimethoxy-1-phenylbutan-1-one Chemical compound COC(Cl)C(OC)CC(=O)C1=CC=CC=C1 YOIBGXUIAJFDER-UHFFFAOYSA-N 0.000 description 4
KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 4
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 4
MFESCIUQSIBMSM-UHFFFAOYSA-N I-BCP Chemical compound ClCCCBr MFESCIUQSIBMSM-UHFFFAOYSA-N 0.000 description 4
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 4
JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 4
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
GPEHQHXBPDGGDP-UHFFFAOYSA-N acetonitrile;propan-2-one Chemical compound CC#N.CC(C)=O GPEHQHXBPDGGDP-UHFFFAOYSA-N 0.000 description 4
230000002378 acidificating effect Effects 0.000 description 4
150000001340 alkali metals Chemical class 0.000 description 4
125000003277 amino group Chemical group 0.000 description 4
150000004945 aromatic hydrocarbons Chemical class 0.000 description 4
239000000460 chlorine Substances 0.000 description 4
UXTMROKLAAOEQO-UHFFFAOYSA-N chloroform;ethanol Chemical compound CCO.ClC(Cl)Cl UXTMROKLAAOEQO-UHFFFAOYSA-N 0.000 description 4
239000013078 crystal Substances 0.000 description 4
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 4
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 4
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
239000008096 xylene Substances 0.000 description 4
229910052727 yttrium Inorganic materials 0.000 description 4
CATQBTMIAAXXND-UHFFFAOYSA-N 2-(3-chloropropyl)-2-(3,4-dimethoxyphenyl)-1,3-dithiane 1,1,3,3-tetraoxide Chemical compound C1=C(OC)C(OC)=CC=C1C1(CCCCl)S(=O)(=O)CCCS1(=O)=O CATQBTMIAAXXND-UHFFFAOYSA-N 0.000 description 3
ZYAIFCGRNDAPLN-UHFFFAOYSA-N 2-[[2-(3,4-dimethoxyphenyl)-1,3-dithian-2-yl]methyl]oxirane Chemical compound C1=C(OC)C(OC)=CC=C1C1(CC2OC2)SCCCS1 ZYAIFCGRNDAPLN-UHFFFAOYSA-N 0.000 description 3
GLVYLTSKTCWWJR-UHFFFAOYSA-N 2-carbonoperoxoylbenzoic acid Chemical compound OOC(=O)C1=CC=CC=C1C(O)=O GLVYLTSKTCWWJR-UHFFFAOYSA-N 0.000 description 3
YOETUEMZNOLGDB-UHFFFAOYSA-N 2-methylpropyl carbonochloridate Chemical compound CC(C)COC(Cl)=O YOETUEMZNOLGDB-UHFFFAOYSA-N 0.000 description 3
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
229910000147 aluminium phosphate Inorganic materials 0.000 description 3
150000001408 amides Chemical class 0.000 description 3
239000002775 capsule Substances 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
238000003776 cleavage reaction Methods 0.000 description 3
238000001816 cooling Methods 0.000 description 3
NPOMSUOUAZCMBL-UHFFFAOYSA-N dichloromethane;ethoxyethane Chemical compound ClCCl.CCOCC NPOMSUOUAZCMBL-UHFFFAOYSA-N 0.000 description 3
230000032050 esterification Effects 0.000 description 3
238000005886 esterification reaction Methods 0.000 description 3
235000019439 ethyl acetate Nutrition 0.000 description 3
238000011065 in-situ storage Methods 0.000 description 3
239000000155 melt Substances 0.000 description 3
229910052987 metal hydride Inorganic materials 0.000 description 3
150000004681 metal hydrides Chemical class 0.000 description 3
125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 3
239000012074 organic phase Substances 0.000 description 3
235000006408 oxalic acid Nutrition 0.000 description 3
150000004965 peroxy acids Chemical class 0.000 description 3
230000007017 scission Effects 0.000 description 3
229910000029 sodium carbonate Inorganic materials 0.000 description 3
229910052938 sodium sulfate Inorganic materials 0.000 description 3
235000011152 sodium sulphate Nutrition 0.000 description 3
239000000126 substance Substances 0.000 description 3
150000003512 tertiary amines Chemical class 0.000 description 3
239000000052 vinegar Substances 0.000 description 3
235000021419 vinegar Nutrition 0.000 description 3
DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 2
ADRVWTYHWDZXFF-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-2-(oxiran-2-ylmethyl)-1,3-dithiane 1,1,3,3-tetraoxide Chemical compound C1=C(OC)C(OC)=CC=C1C1(CC2OC2)S(=O)(=O)CCCS1(=O)=O ADRVWTYHWDZXFF-UHFFFAOYSA-N 0.000 description 2
FEEDFNKRGAKOFI-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)ethyl-[3-[2-(3,4-dimethoxyphenyl)-1,1,3,3-tetraoxo-1,3-dithian-2-yl]propyl]-methylazanium;chloride Chemical compound [Cl-].C1=C(OC)C(OC)=CC=C1CC[NH+](C)CCCC1(C=2C=C(OC)C(OC)=CC=2)S(=O)(=O)CCCS1(=O)=O FEEDFNKRGAKOFI-UHFFFAOYSA-N 0.000 description 2
QWKZHSATRDJODU-UHFFFAOYSA-N 2-(3-chloropropyl)-2-(3,4-dimethoxyphenyl)-1,3-dithiane 1,3-dioxide Chemical compound C1=C(OC)C(OC)=CC=C1C1(CCCCl)S(=O)CCCS1=O QWKZHSATRDJODU-UHFFFAOYSA-N 0.000 description 2
HSYKXUHKZHKUQA-UHFFFAOYSA-N 2-(3-chloropropyl)-2-phenyl-1,3-dithiane 1,1,3,3-tetraoxide Chemical compound C=1C=CC=CC=1C1(CCCCl)S(=O)(=O)CCCS1(=O)=O HSYKXUHKZHKUQA-UHFFFAOYSA-N 0.000 description 2
GIHYCFJFKPVUGQ-UHFFFAOYSA-N 3-[2-(3,4-dimethoxyphenyl)-1,1,3,3-tetraoxo-1,3-dithian-2-yl]-n-methylpropan-1-amine Chemical compound C=1C=C(OC)C(OC)=CC=1C1(CCCNC)S(=O)(=O)CCCS1(=O)=O GIHYCFJFKPVUGQ-UHFFFAOYSA-N 0.000 description 2
NZIYMXRIWYDZGJ-UHFFFAOYSA-N 3-[2-(3,4-dimethoxyphenyl)-1,3-dithian-2-yl]-n-[2-(3,4-dimethoxyphenyl)ethyl]-n-methylpropan-1-amine;hydrobromide Chemical compound Br.C1=C(OC)C(OC)=CC=C1CCN(C)CCCC1(C=2C=C(OC)C(OC)=CC=2)SCCCS1 NZIYMXRIWYDZGJ-UHFFFAOYSA-N 0.000 description 2
IXADASBXSLCGOW-UHFFFAOYSA-N 3-[2-(3,4-dimethoxyphenyl)-1,3-dithian-2-yl]-n-[2-(3,4-dimethoxyphenyl)ethyl]propanamide Chemical compound C1=C(OC)C(OC)=CC=C1CCNC(=O)CCC1(C=2C=C(OC)C(OC)=CC=2)SCCCS1 IXADASBXSLCGOW-UHFFFAOYSA-N 0.000 description 2
ASLKIHDOGVHGDY-UHFFFAOYSA-N 3-[2-(3,4-dimethoxyphenyl)-1,3-dithian-2-yl]propanoic acid Chemical compound C1=C(OC)C(OC)=CC=C1C1(CCC(O)=O)SCCCS1 ASLKIHDOGVHGDY-UHFFFAOYSA-N 0.000 description 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 2
BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 2
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