DE209695C - - Google Patents

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Publication number

DE209695C

DE209695C DENDAT209695D DE209695DA DE209695C DE 209695 C DE209695 C DE 209695C DE NDAT209695 D DENDAT209695 D DE NDAT209695D DE 209695D A DE209695D A DE 209695DA DE 209695 C DE209695 C DE 209695C

Authority

DE

Germany

Prior art keywords

salt

salts

sodium

acid

percent

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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• WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 9
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 8
• IMPPGHMHELILKG-UHFFFAOYSA-N 4-ethoxyaniline Chemical compound CCOC1=CC=C(N)C=C1 IMPPGHMHELILKG-UHFFFAOYSA-N 0.000 claims description 5
• 238000000034 method Methods 0.000 claims description 5
• QMLLUTUQHWNQQS-UHFFFAOYSA-N CCOC(C=C1)=CC=C1NCS(O)(O)=O Chemical class CCOC(C=C1)=CC=C1NCS(O)(O)=O QMLLUTUQHWNQQS-UHFFFAOYSA-N 0.000 claims description 4
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 4
• 238000002360 preparation method Methods 0.000 claims description 2
• AOSFMYBATFLTAQ-UHFFFAOYSA-N 1-amino-3-(benzimidazol-1-yl)propan-2-ol Chemical compound C1=CC=C2N(CC(O)CN)C=NC2=C1 AOSFMYBATFLTAQ-UHFFFAOYSA-N 0.000 claims 1
• 239000003513 alkali Substances 0.000 claims 1
• 150000003839 salts Chemical class 0.000 description 12
• 239000000243 solution Substances 0.000 description 6
• 239000002253 acid Substances 0.000 description 5
• 239000000047 product Substances 0.000 description 5
• PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
• 230000001225 therapeutic effect Effects 0.000 description 4
• LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 3
• 239000013078 crystal Substances 0.000 description 3
• 238000000354 decomposition reaction Methods 0.000 description 3
• CPJSUEIXXCENMM-UHFFFAOYSA-N phenacetin Chemical compound CCOC1=CC=C(NC(C)=O)C=C1 CPJSUEIXXCENMM-UHFFFAOYSA-N 0.000 description 3
• -1 sodium p-ethoxyphenylaminomethylsulfur Chemical compound 0.000 description 3
• 159000000000 sodium salts Chemical class 0.000 description 3
• DETXZQGDWUJKMO-UHFFFAOYSA-N 2-hydroxymethanesulfonic acid Chemical compound OCS(O)(=O)=O DETXZQGDWUJKMO-UHFFFAOYSA-N 0.000 description 2
• PLIKAWJENQZMHA-UHFFFAOYSA-N 4-aminophenol Chemical compound NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 description 2
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
• 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 2
• 150000003863 ammonium salts Chemical class 0.000 description 2
• 230000001754 anti-pyretic effect Effects 0.000 description 2
• 239000007864 aqueous solution Substances 0.000 description 2
• 238000009835 boiling Methods 0.000 description 2
• 238000006243 chemical reaction Methods 0.000 description 2
• 150000001875 compounds Chemical class 0.000 description 2
• 239000007859 condensation product Substances 0.000 description 2
• 229960003893 phenacetin Drugs 0.000 description 2
• XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 2
• 238000001556 precipitation Methods 0.000 description 2
• 238000001953 recrystallisation Methods 0.000 description 2
• SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 2
• 229910052708 sodium Inorganic materials 0.000 description 2
• 239000011734 sodium Substances 0.000 description 2
• 238000003786 synthesis reaction Methods 0.000 description 2
• 231100000419 toxicity Toxicity 0.000 description 2
• 230000001988 toxicity Effects 0.000 description 2
• PRWQMQQGSFHEJJ-UHFFFAOYSA-N C1(=CC=CC=C1)NCS(O)(O)=O Chemical class C1(=CC=CC=C1)NCS(O)(O)=O PRWQMQQGSFHEJJ-UHFFFAOYSA-N 0.000 description 1
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
• 229910021578 Iron(III) chloride Inorganic materials 0.000 description 1
• FZERHIULMFGESH-UHFFFAOYSA-N N-phenylacetamide Chemical compound CC(=O)NC1=CC=CC=C1 FZERHIULMFGESH-UHFFFAOYSA-N 0.000 description 1
• ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
• 239000002262 Schiff base Substances 0.000 description 1
• 150000004753 Schiff bases Chemical class 0.000 description 1
• DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
• ZUYFLSARRQBQPE-UHFFFAOYSA-M [Cl-].[Ba+] Chemical compound [Cl-].[Ba+] ZUYFLSARRQBQPE-UHFFFAOYSA-M 0.000 description 1
• 150000007513 acids Chemical class 0.000 description 1
• 239000007900 aqueous suspension Substances 0.000 description 1
• 150000004982 aromatic amines Chemical class 0.000 description 1
• 125000003118 aryl group Chemical group 0.000 description 1
• ZETCGWYACBNPIH-UHFFFAOYSA-N azane;sulfurous acid Chemical compound N.OS(O)=O ZETCGWYACBNPIH-UHFFFAOYSA-N 0.000 description 1
• 159000000009 barium salts Chemical class 0.000 description 1
• 239000002585 base Substances 0.000 description 1
• 230000009286 beneficial effect Effects 0.000 description 1
• 230000015572 biosynthetic process Effects 0.000 description 1
• 230000000747 cardiac effect Effects 0.000 description 1
• 235000009508 confectionery Nutrition 0.000 description 1
• SOCTUWSJJQCPFX-UHFFFAOYSA-N dichromate(2-) Chemical compound [O-][Cr](=O)(=O)O[Cr]([O-])(=O)=O SOCTUWSJJQCPFX-UHFFFAOYSA-N 0.000 description 1
• 238000004090 dissolution Methods 0.000 description 1
• 230000000694 effects Effects 0.000 description 1
• 125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 1
• 239000012458 free base Substances 0.000 description 1
• 238000011835 investigation Methods 0.000 description 1
• RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
• GHZNWXGYWUBLLI-UHFFFAOYSA-N p-Lactophenetide Chemical compound CCOC1=CC=C(NC(=O)C(C)O)C=C1 GHZNWXGYWUBLLI-UHFFFAOYSA-N 0.000 description 1
• 230000000144 pharmacologic effect Effects 0.000 description 1
• 229910052700 potassium Inorganic materials 0.000 description 1
• 239000011591 potassium Substances 0.000 description 1
• 238000010992 reflux Methods 0.000 description 1
• 230000001105 regulatory effect Effects 0.000 description 1
• 229920006395 saturated elastomer Polymers 0.000 description 1
• 239000012047 saturated solution Substances 0.000 description 1
• 229910052709 silver Inorganic materials 0.000 description 1
• 239000004332 silver Substances 0.000 description 1
• 229910001961 silver nitrate Inorganic materials 0.000 description 1
• ORFSSYGWXNGVFB-UHFFFAOYSA-N sodium 4-amino-6-[[4-[4-[(8-amino-1-hydroxy-5,7-disulfonaphthalen-2-yl)diazenyl]-3-methoxyphenyl]-2-methoxyphenyl]diazenyl]-5-hydroxynaphthalene-1,3-disulfonic acid Chemical compound COC1=C(C=CC(=C1)C2=CC(=C(C=C2)N=NC3=C(C4=C(C=C3)C(=CC(=C4N)S(=O)(=O)O)S(=O)(=O)O)O)OC)N=NC5=C(C6=C(C=C5)C(=CC(=C6N)S(=O)(=O)O)S(=O)(=O)O)O.[Na+] ORFSSYGWXNGVFB-UHFFFAOYSA-N 0.000 description 1
• 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
• 238000010186 staining Methods 0.000 description 1
• 238000003756 stirring Methods 0.000 description 1
• 150000004992 toluidines Chemical class 0.000 description 1
• 231100000331 toxic Toxicity 0.000 description 1
• 230000002588 toxic effect Effects 0.000 description 1