DE2325300A1 - Cyclische schwefelverbindungen - Google Patents

Info

Publication number

DE2325300A1

DE2325300A1 DE2325300A DE2325300A DE2325300A1 DE 2325300 A1 DE2325300 A1 DE 2325300A1 DE 2325300 A DE2325300 A DE 2325300A DE 2325300 A DE2325300 A DE 2325300A DE 2325300 A1 DE2325300 A1 DE 2325300A1

Authority

DE

Germany

Prior art keywords

group

alkyl

tetrazolyl

dioxide

acid

Prior art date

1972-05-19

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.)

Pending

Links

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• 150000003464 sulfur compounds Chemical class 0.000 title 1
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 259
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 169
• 238000002844 melting Methods 0.000 claims description 139
• 230000008018 melting Effects 0.000 claims description 138
• 150000001875 compounds Chemical class 0.000 claims description 136
• 238000002360 preparation method Methods 0.000 claims description 116
• -1 5-tetrazolyl Chemical group 0.000 claims description 106
• 125000000217 alkyl group Chemical group 0.000 claims description 103
• 239000000203 mixture Substances 0.000 claims description 99
• 150000003839 salts Chemical class 0.000 claims description 88
• 125000001424 substituent group Chemical group 0.000 claims description 67
• 125000004432 carbon atom Chemical group C* 0.000 claims description 64
• 239000007787 solid Substances 0.000 claims description 61
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 57
• MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 53
• 238000000034 method Methods 0.000 claims description 53
• 239000000825 pharmaceutical preparation Substances 0.000 claims description 47
• 239000002253 acid Substances 0.000 claims description 44
• 125000002252 acyl group Chemical group 0.000 claims description 41
• 150000001408 amides Chemical class 0.000 claims description 41
• 125000003545 alkoxy group Chemical group 0.000 claims description 39
• 125000004442 acylamino group Chemical group 0.000 claims description 38
• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 37
• 125000003831 tetrazolyl group Chemical group 0.000 claims description 34
• 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 33
• 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 33
• 239000000843 powder Substances 0.000 claims description 31
• 150000002148 esters Chemical class 0.000 claims description 30
• 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 30
• 125000004001 thioalkyl group Chemical group 0.000 claims description 29
• 239000003380 propellant Substances 0.000 claims description 27
• 238000009835 boiling Methods 0.000 claims description 26
• 230000002378 acidificating effect Effects 0.000 claims description 25
• 238000004519 manufacturing process Methods 0.000 claims description 25
• 229910052717 sulfur Inorganic materials 0.000 claims description 25
• 150000003462 sulfoxides Chemical class 0.000 claims description 24
• 230000015572 biosynthetic process Effects 0.000 claims description 23
• 239000000460 chlorine Substances 0.000 claims description 23
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 22
• 238000006243 chemical reaction Methods 0.000 claims description 22
• 229910052801 chlorine Inorganic materials 0.000 claims description 22
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 22
• 239000007788 liquid Substances 0.000 claims description 22
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 21
• 239000002245 particle Substances 0.000 claims description 21
• 239000002585 base Substances 0.000 claims description 20
• 239000007789 gas Substances 0.000 claims description 20
• 238000010438 heat treatment Methods 0.000 claims description 20
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 20
• 239000011734 sodium Substances 0.000 claims description 20
• 229910052708 sodium Inorganic materials 0.000 claims description 20
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 19
• 239000000443 aerosol Substances 0.000 claims description 19
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 18
• 229910052794 bromium Inorganic materials 0.000 claims description 18
• 229910052760 oxygen Inorganic materials 0.000 claims description 18
• 239000001301 oxygen Substances 0.000 claims description 18
• 239000002243 precursor Substances 0.000 claims description 18
• DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical group 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 claims description 17
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 17
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 17
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 16
• 125000005843 halogen group Chemical group 0.000 claims description 16
• 230000008569 process Effects 0.000 claims description 15
• 239000003937 drug carrier Substances 0.000 claims description 14
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 14
• NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical group CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims description 13
• 159000000000 sodium salts Chemical class 0.000 claims description 12
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 11
• 125000005599 alkyl carboxylate group Chemical group 0.000 claims description 11
• 239000002775 capsule Substances 0.000 claims description 11
• 229910052736 halogen Inorganic materials 0.000 claims description 11
• 150000002367 halogens Chemical class 0.000 claims description 11
• 125000003277 amino group Chemical group 0.000 claims description 10
• 150000001768 cations Chemical class 0.000 claims description 10
• 239000011593 sulfur Substances 0.000 claims description 10
• 229910052727 yttrium Inorganic materials 0.000 claims description 10
• 210000004072 lung Anatomy 0.000 claims description 9
• VIDCTSLIEZMQRF-UHFFFAOYSA-N 10,10-dioxo-3-(2h-tetrazol-5-yl)thioxanthen-9-one Chemical compound C=1C=C2C(=O)C3=CC=CC=C3S(=O)(=O)C2=CC=1C=1N=NNN=1 VIDCTSLIEZMQRF-UHFFFAOYSA-N 0.000 claims description 8
• KTMTUGYSHWKLNN-UHFFFAOYSA-N 9,10,10-trioxothioxanthene-3-carboxylic acid Chemical compound C1=CC=C2S(=O)(=O)C3=CC(C(=O)O)=CC=C3C(=O)C2=C1 KTMTUGYSHWKLNN-UHFFFAOYSA-N 0.000 claims description 8
• 125000004429 atom Chemical group 0.000 claims description 8
• 229940117975 chromium trioxide Drugs 0.000 claims description 8
• WGLPBDUCMAPZCE-UHFFFAOYSA-N chromium trioxide Inorganic materials O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 claims description 8
• GAMDZJFZMJECOS-UHFFFAOYSA-N chromium(6+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[Cr+6] GAMDZJFZMJECOS-UHFFFAOYSA-N 0.000 claims description 8
• RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 7
• 229910052783 alkali metal Inorganic materials 0.000 claims description 7
• 150000004702 methyl esters Chemical class 0.000 claims description 7
• 150000003254 radicals Chemical class 0.000 claims description 7
• 239000002841 Lewis acid Substances 0.000 claims description 6
• YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 6
• 125000005392 carboxamide group Chemical group NC(=O)* 0.000 claims description 6
• 229930195733 hydrocarbon Natural products 0.000 claims description 6
• JUINSXZKUKVTMD-UHFFFAOYSA-N hydrogen azide Chemical compound N=[N+]=[N-] JUINSXZKUKVTMD-UHFFFAOYSA-N 0.000 claims description 6
• 150000007517 lewis acids Chemical class 0.000 claims description 6
• 239000007800 oxidant agent Substances 0.000 claims description 6
• 239000004094 surface-active agent Substances 0.000 claims description 6
• GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims description 5
• 150000007513 acids Chemical class 0.000 claims description 5
• 229910052802 copper Inorganic materials 0.000 claims description 5
• 239000010949 copper Substances 0.000 claims description 5
• 229910017604 nitric acid Inorganic materials 0.000 claims description 5
• 150000007530 organic bases Chemical class 0.000 claims description 5
• FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 4
• IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 claims description 4
• GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 4
• 229910052782 aluminium Inorganic materials 0.000 claims description 4
• XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 4
• WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 claims description 4
• 239000011777 magnesium Substances 0.000 claims description 4
• 229910052749 magnesium Inorganic materials 0.000 claims description 4
• 125000004430 oxygen atom Chemical group O* 0.000 claims description 4
• 230000009467 reduction Effects 0.000 claims description 4
• 230000002829 reductive effect Effects 0.000 claims description 4
• 238000007363 ring formation reaction Methods 0.000 claims description 4
• KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 claims description 3
• QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 3
• 239000003513 alkali Substances 0.000 claims description 3
• 150000003863 ammonium salts Chemical class 0.000 claims description 3
• 239000003054 catalyst Substances 0.000 claims description 3
• XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 claims description 3
• 150000001923 cyclic compounds Chemical class 0.000 claims description 3
• 125000002560 nitrile group Chemical group 0.000 claims description 3
• 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 3
• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 3
• URUXPTBGYCJMMI-UHFFFAOYSA-N 7-nitro-9,10,10-trioxothioxanthene-2-carboxylic acid Chemical compound [O-][N+](=O)C1=CC=C2S(=O)(=O)C3=CC=C(C(=O)O)C=C3C(=O)C2=C1 URUXPTBGYCJMMI-UHFFFAOYSA-N 0.000 claims description 2
• 229910015900 BF3 Inorganic materials 0.000 claims description 2
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
• QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 claims description 2
• RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical group O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 claims description 2
• GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 claims description 2
• 229910052799 carbon Inorganic materials 0.000 claims description 2
• IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical group [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 claims description 2
• SOCTUWSJJQCPFX-UHFFFAOYSA-N dichromate(2-) Chemical class [O-][Cr](=O)(=O)O[Cr]([O-])(=O)=O SOCTUWSJJQCPFX-UHFFFAOYSA-N 0.000 claims description 2
• 238000009472 formulation Methods 0.000 claims description 2
• CUILPNURFADTPE-UHFFFAOYSA-N hypobromous acid Chemical compound BrO CUILPNURFADTPE-UHFFFAOYSA-N 0.000 claims description 2
• 229910052500 inorganic mineral Inorganic materials 0.000 claims description 2
• 239000007791 liquid phase Substances 0.000 claims description 2
• OJURWUUOVGOHJZ-UHFFFAOYSA-N methyl 2-[(2-acetyloxyphenyl)methyl-[2-[(2-acetyloxyphenyl)methyl-(2-methoxy-2-oxoethyl)amino]ethyl]amino]acetate Chemical compound C=1C=CC=C(OC(C)=O)C=1CN(CC(=O)OC)CCN(CC(=O)OC)CC1=CC=CC=C1OC(C)=O OJURWUUOVGOHJZ-UHFFFAOYSA-N 0.000 claims description 2
• 239000011707 mineral Substances 0.000 claims description 2
• 238000006396 nitration reaction Methods 0.000 claims description 2
• 229910052979 sodium sulfide Inorganic materials 0.000 claims description 2
• GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 claims description 2
• PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 claims description 2
• 125000004434 sulfur atom Chemical group 0.000 claims 15
• ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims 4
• 239000011591 potassium Substances 0.000 claims 4
• 229910052700 potassium Inorganic materials 0.000 claims 4
• NLLBEEJQCHRDQG-UHFFFAOYSA-N 8-chloro-10,10-dioxophenoxathiine-2-carboxylic acid Chemical compound C1=C(Cl)C=C2S(=O)(=O)C3=CC(C(=O)O)=CC=C3OC2=C1 NLLBEEJQCHRDQG-UHFFFAOYSA-N 0.000 claims 3
• 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims 3
• 239000008194 pharmaceutical composition Substances 0.000 claims 3
• AJLLKBKSHTWSHL-UHFFFAOYSA-N 9-nitro-10,10-dioxophenoxathiine-4-carboxylic acid Chemical compound O1C2=CC=CC([N+]([O-])=O)=C2S(=O)(=O)C2=C1C(C(=O)O)=CC=C2 AJLLKBKSHTWSHL-UHFFFAOYSA-N 0.000 claims 2
• OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims 2
• GQPLMRYTRLFLPF-UHFFFAOYSA-N Nitrous Oxide Chemical compound [O-][N+]#N GQPLMRYTRLFLPF-UHFFFAOYSA-N 0.000 claims 2
• 239000011575 calcium Substances 0.000 claims 2
• 229910052791 calcium Inorganic materials 0.000 claims 2
• 230000000269 nucleophilic effect Effects 0.000 claims 2
• 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 claims 2
• AVWMOHMIEPITMO-UHFFFAOYSA-N 3-(2h-tetrazol-5-yl)-9h-thioxanthene 10,10-dioxide Chemical compound C1=C2S(=O)(=O)C3=CC=CC=C3CC2=CC=C1C=1N=NNN=1 AVWMOHMIEPITMO-UHFFFAOYSA-N 0.000 claims 1
• KFTPXAFBDZWJNK-UHFFFAOYSA-N 9,10,10-trioxothioxanthene-3-carbonitrile Chemical compound N#CC1=CC=C2C(=O)C3=CC=CC=C3S(=O)(=O)C2=C1 KFTPXAFBDZWJNK-UHFFFAOYSA-N 0.000 claims 1
• MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims 1
• ATTZFSUZZUNHBP-UHFFFAOYSA-N Piperonyl sulfoxide Chemical group CCCCCCCCS(=O)C(C)CC1=CC=C2OCOC2=C1 ATTZFSUZZUNHBP-UHFFFAOYSA-N 0.000 claims 1
• 125000003172 aldehyde group Chemical group 0.000 claims 1
• 150000003857 carboxamides Chemical class 0.000 claims 1
• 150000007942 carboxylates Chemical class 0.000 claims 1
• 239000003795 chemical substances by application Substances 0.000 claims 1
• 125000004494 ethyl ester group Chemical group 0.000 claims 1
• 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims 1
• QWPPOHNGKGFGJK-UHFFFAOYSA-N hypochlorous acid Chemical compound ClO QWPPOHNGKGFGJK-UHFFFAOYSA-N 0.000 claims 1
• 150000003949 imides Chemical class 0.000 claims 1
• 159000000003 magnesium salts Chemical class 0.000 claims 1
• UDGSVBYJWHOHNN-UHFFFAOYSA-N n',n'-diethylethane-1,2-diamine Chemical compound CCN(CC)CCN UDGSVBYJWHOHNN-UHFFFAOYSA-N 0.000 claims 1
• 239000001272 nitrous oxide Substances 0.000 claims 1
• XJLRCPYQIPAQCA-UHFFFAOYSA-N phenoxathiine 10,10-dioxide Chemical compound C1=CC=C2S(=O)(=O)C3=CC=CC=C3OC2=C1 XJLRCPYQIPAQCA-UHFFFAOYSA-N 0.000 claims 1
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 153
• 239000000243 solution Substances 0.000 description 134
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 86
• 229960000583 acetic acid Drugs 0.000 description 86
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 78
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 57
• 239000000047 product Substances 0.000 description 56
• FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 54
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 51
• 238000004458 analytical method Methods 0.000 description 39
• 239000004480 active ingredient Substances 0.000 description 35
• 238000001816 cooling Methods 0.000 description 29
• 235000019441 ethanol Nutrition 0.000 description 29
• NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 28
• 229960002163 hydrogen peroxide Drugs 0.000 description 25
• PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 24
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 22
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 21
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 20
• 238000003756 stirring Methods 0.000 description 18
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
• QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 14
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 14
• 238000001953 recrystallisation Methods 0.000 description 14
• 238000010992 reflux Methods 0.000 description 14
• VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 13
• 235000019270 ammonium chloride Nutrition 0.000 description 13
• 239000002904 solvent Substances 0.000 description 13
• 238000011282 treatment Methods 0.000 description 13
• 150000001732 carboxylic acid derivatives Chemical class 0.000 description 12
• 239000001257 hydrogen Substances 0.000 description 12
• 229910052739 hydrogen Inorganic materials 0.000 description 12
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 11
• 239000007864 aqueous solution Substances 0.000 description 11
• 229960001760 dimethyl sulfoxide Drugs 0.000 description 11
• 239000002244 precipitate Substances 0.000 description 11
• 239000011541 reaction mixture Substances 0.000 description 11
• 229910021529 ammonia Inorganic materials 0.000 description 10
• 239000004615 ingredient Substances 0.000 description 10
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 9
• 208000006673 asthma Diseases 0.000 description 9
• 238000000354 decomposition reaction Methods 0.000 description 9
• 239000006196 drop Substances 0.000 description 9
• 239000000725 suspension Substances 0.000 description 9
• 239000003826 tablet Substances 0.000 description 9
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
• KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 8
• 239000000706 filtrate Substances 0.000 description 8
• 238000001914 filtration Methods 0.000 description 8
• HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 8
• 150000002825 nitriles Chemical class 0.000 description 8
• 229920000137 polyphosphoric acid Polymers 0.000 description 8
• KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 7
• 239000013078 crystal Substances 0.000 description 7
• 239000000463 material Substances 0.000 description 7
• 230000003647 oxidation Effects 0.000 description 7
• 238000007254 oxidation reaction Methods 0.000 description 7
• 229920000036 polyvinylpyrrolidone Polymers 0.000 description 7
• 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 7
• 239000008213 purified water Substances 0.000 description 7
• 235000017557 sodium bicarbonate Nutrition 0.000 description 7
• 229910000030 sodium bicarbonate Inorganic materials 0.000 description 7
• 239000012265 solid product Substances 0.000 description 7
• WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
• 229920002261 Corn starch Polymers 0.000 description 6
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
• 239000004606 Fillers/Extenders Substances 0.000 description 6
• PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
• WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 6
• HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 6
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