DE210564C - - Google Patents

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Publication number

DE210564C

DE210564C DENDAT210564D DE210564DA DE210564C DE 210564 C DE210564 C DE 210564C DE NDAT210564 D DENDAT210564 D DE NDAT210564D DE 210564D A DE210564D A DE 210564DA DE 210564 C DE210564 C DE 210564C

Authority

DE

Germany

Prior art keywords

acid

sodium

nitrothiophenol

thioaniline

parts

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.)

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• 239000002253 acid Substances 0.000 claims description 7
• 239000000243 solution Substances 0.000 claims description 6
• 238000009835 boiling Methods 0.000 claims description 5
• AXBVSRMHOPMXBA-UHFFFAOYSA-N 4-nitrothiophenol Chemical compound [O-][N+](=O)C1=CC=C(S)C=C1 AXBVSRMHOPMXBA-UHFFFAOYSA-N 0.000 claims description 4
• 239000012670 alkaline solution Substances 0.000 claims description 4
• 238000006243 chemical reaction Methods 0.000 claims description 4
• 238000000034 method Methods 0.000 claims description 3
• 159000000000 sodium salts Chemical class 0.000 claims description 3
• 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 claims description 2
• 239000007864 aqueous solution Substances 0.000 claims description 2
• 239000003638 chemical reducing agent Substances 0.000 claims description 2
• 238000010992 reflux Methods 0.000 claims description 2
• 239000011734 sodium Substances 0.000 claims description 2
• 229910052708 sodium Inorganic materials 0.000 claims description 2
• ICNFHJVPAJKPHW-UHFFFAOYSA-N 4,4'-Thiodianiline Chemical compound C1=CC(N)=CC=C1SC1=CC=C(N)C=C1 ICNFHJVPAJKPHW-UHFFFAOYSA-N 0.000 claims 2
• 150000003460 sulfonic acids Chemical class 0.000 claims 2
• WYIXHEJIUZZJLJ-UHFFFAOYSA-N 1-(2,3-dinitrophenyl)sulfanyl-2,3-dinitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC(SC=2C(=C(C=CC=2)[N+]([O-])=O)[N+]([O-])=O)=C1[N+]([O-])=O WYIXHEJIUZZJLJ-UHFFFAOYSA-N 0.000 claims 1
• KIXANWDXDRBCLI-UHFFFAOYSA-N 2-chloro-4-nitrobenzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=C([N+]([O-])=O)C=C1Cl KIXANWDXDRBCLI-UHFFFAOYSA-N 0.000 claims 1
• BTJIUGUIPKRLHP-UHFFFAOYSA-N 4-nitrophenol Chemical compound OC1=CC=C([N+]([O-])=O)C=C1 BTJIUGUIPKRLHP-UHFFFAOYSA-N 0.000 claims 1
• 239000013078 crystal Substances 0.000 claims 1
• 238000002360 preparation method Methods 0.000 claims 1
• PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 6
• LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 5
• HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 4
• 229910052801 chlorine Inorganic materials 0.000 description 4
• RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 4
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
• 239000000460 chlorine Substances 0.000 description 3
• 238000009833 condensation Methods 0.000 description 3
• 230000005494 condensation Effects 0.000 description 3
• LTYMSROWYAPPGB-UHFFFAOYSA-N diphenyl sulfide Chemical class C=1C=CC=CC=1SC1=CC=CC=C1 LTYMSROWYAPPGB-UHFFFAOYSA-N 0.000 description 3
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
• QWIWYBUPJLCBSE-UHFFFAOYSA-N 3-chloro-2-nitrobenzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC(Cl)=C1[N+]([O-])=O QWIWYBUPJLCBSE-UHFFFAOYSA-N 0.000 description 2
• WYFNYCOJHYLRHJ-UHFFFAOYSA-N 4-nitrobenzenethiol;sodium Chemical compound [Na].[O-][N+](=O)C1=CC=C(S)C=C1 WYFNYCOJHYLRHJ-UHFFFAOYSA-N 0.000 description 2
• CHBFUBKXMBQCKO-UHFFFAOYSA-N 5-amino-2-(4-amino-2-sulfophenyl)sulfanylbenzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC(N)=CC=C1SC1=CC=C(N)C=C1S(O)(=O)=O CHBFUBKXMBQCKO-UHFFFAOYSA-N 0.000 description 2
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
• 150000007513 acids Chemical class 0.000 description 2
• 230000015572 biosynthetic process Effects 0.000 description 2
• 239000000843 powder Substances 0.000 description 2
• 239000000047 product Substances 0.000 description 2
• JKIFPWHZEZQCQA-UHFFFAOYSA-N 2-nitrobenzenethiol Chemical compound [O-][N+](=O)C1=CC=CC=C1S JKIFPWHZEZQCQA-UHFFFAOYSA-N 0.000 description 1
• QTRNDORTMVTOEG-UHFFFAOYSA-N [O-][N+](=O)OS(=O)(=O)[N+]([O-])=O Chemical compound [O-][N+](=O)OS(=O)(=O)[N+]([O-])=O QTRNDORTMVTOEG-UHFFFAOYSA-N 0.000 description 1
• 230000001476 alcoholic effect Effects 0.000 description 1
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
• 229910052794 bromium Inorganic materials 0.000 description 1
• 239000012295 chemical reaction liquid Substances 0.000 description 1
• 125000001309 chloro group Chemical group Cl* 0.000 description 1
• 238000001914 filtration Methods 0.000 description 1
• 239000012452 mother liquor Substances 0.000 description 1
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
• -1 p-nitrochlorobenzenesulfonic acid Sodium Chemical compound 0.000 description 1
• 239000002244 precipitate Substances 0.000 description 1
• 230000002035 prolonged effect Effects 0.000 description 1
• 150000003839 salts Chemical class 0.000 description 1
• PROMGPNHMOSZSZ-UHFFFAOYSA-M sodium 4-chloro-2-nitrobenzenesulfonate Chemical compound [Na+].[O-][N+](=O)c1cc(Cl)ccc1S([O-])(=O)=O PROMGPNHMOSZSZ-UHFFFAOYSA-M 0.000 description 1
• 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1