PL54012B1 - - Google Patents

Info

Publication number

PL54012B1

PL54012B1 PL108460A PL10846065A PL54012B1 PL 54012 B1 PL54012 B1 PL 54012B1 PL 108460 A PL108460 A PL 108460A PL 10846065 A PL10846065 A PL 10846065A PL 54012 B1 PL54012 B1 PL 54012B1

Authority

PL

Poland

Prior art keywords

aminophenol

nitrosophenol

acetyl

water

phenol

Prior art date

1965-04-20

Links

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• PLIKAWJENQZMHA-UHFFFAOYSA-N 4-aminophenol Chemical compound NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 claims description 42
• WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 15
• JSTCPNFNKICNNO-UHFFFAOYSA-N 4-nitrosophenol Chemical compound OC1=CC=C(N=O)C=C1 JSTCPNFNKICNNO-UHFFFAOYSA-N 0.000 claims description 11
• RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 claims description 11
• 238000000034 method Methods 0.000 claims description 9
• 230000021736 acetylation Effects 0.000 claims description 5
• 238000006640 acetylation reaction Methods 0.000 claims description 5
• 230000009467 reduction Effects 0.000 claims description 5
• BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 claims description 4
• 238000002360 preparation method Methods 0.000 claims description 4
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 claims description 3
• 229910052921 ammonium sulfate Inorganic materials 0.000 claims description 3
• 239000001166 ammonium sulphate Substances 0.000 claims description 3
• 235000011130 ammonium sulphate Nutrition 0.000 claims description 3
• 239000012047 saturated solution Substances 0.000 claims description 3
• 239000012736 aqueous medium Substances 0.000 claims description 2
• 230000001376 precipitating effect Effects 0.000 claims description 2
• 229910052938 sodium sulfate Inorganic materials 0.000 claims description 2
• 235000011152 sodium sulphate Nutrition 0.000 claims description 2
• JVUOZFIKJGZTCN-UHFFFAOYSA-N 4-aminophenol;sodium Chemical compound [Na].NC1=CC=C(O)C=C1 JVUOZFIKJGZTCN-UHFFFAOYSA-N 0.000 claims 1
• 239000012429 reaction media Substances 0.000 claims 1
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
• 239000000243 solution Substances 0.000 description 7
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
• 238000002425 crystallisation Methods 0.000 description 5
• 230000008025 crystallization Effects 0.000 description 5
• 238000000746 purification Methods 0.000 description 4
• GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 description 4
• 238000006243 chemical reaction Methods 0.000 description 3
• 238000003756 stirring Methods 0.000 description 3
• 238000005406 washing Methods 0.000 description 3
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
• CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
• ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
• 239000007864 aqueous solution Substances 0.000 description 2
• 239000003814 drug Substances 0.000 description 2
• 229940079593 drug Drugs 0.000 description 2
• 238000004519 manufacturing process Methods 0.000 description 2
• LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
• 239000002244 precipitate Substances 0.000 description 2
• 239000000047 product Substances 0.000 description 2
• 239000011541 reaction mixture Substances 0.000 description 2
• LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
• 229910052979 sodium sulfide Inorganic materials 0.000 description 2
• QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 1
• NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
• VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
• RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
• 239000007832 Na2SO4 Substances 0.000 description 1
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
• TUCNEACPLKLKNU-UHFFFAOYSA-N acetyl Chemical compound C[C]=O TUCNEACPLKLKNU-UHFFFAOYSA-N 0.000 description 1
• 235000011114 ammonium hydroxide Nutrition 0.000 description 1
• 239000001569 carbon dioxide Substances 0.000 description 1
• 229910002092 carbon dioxide Inorganic materials 0.000 description 1
• 238000005119 centrifugation Methods 0.000 description 1
• 210000000078 claw Anatomy 0.000 description 1
• 150000001875 compounds Chemical class 0.000 description 1
• 238000004042 decolorization Methods 0.000 description 1
• 239000012153 distilled water Substances 0.000 description 1
• 238000001035 drying Methods 0.000 description 1
• 229910052949 galena Inorganic materials 0.000 description 1
• 230000005484 gravity Effects 0.000 description 1
• 238000000227 grinding Methods 0.000 description 1
• 229910052739 hydrogen Inorganic materials 0.000 description 1
• 239000001257 hydrogen Substances 0.000 description 1
• -1 hydrogen ions Chemical class 0.000 description 1
• 239000005457 ice water Substances 0.000 description 1
• XCAUINMIESBTBL-UHFFFAOYSA-N lead(ii) sulfide Chemical compound [Pb]=S XCAUINMIESBTBL-UHFFFAOYSA-N 0.000 description 1
• 238000002156 mixing Methods 0.000 description 1
• 239000000203 mixture Substances 0.000 description 1
• 150000002832 nitroso derivatives Chemical class 0.000 description 1
• 238000001556 precipitation Methods 0.000 description 1
• 229920006395 saturated elastomer Polymers 0.000 description 1
• 235000010288 sodium nitrite Nutrition 0.000 description 1
• 159000000000 sodium salts Chemical class 0.000 description 1
• AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
• 235000019345 sodium thiosulphate Nutrition 0.000 description 1
• 239000007787 solid Substances 0.000 description 1
• 239000000126 substance Substances 0.000 description 1