GB642013A - Process for the manufacture of a new acylated sulphonamide, and of its salts - Google Patents
Process for the manufacture of a new acylated sulphonamide, and of its saltsInfo
- Publication number
- GB642013A GB642013A GB9300/48A GB930048A GB642013A GB 642013 A GB642013 A GB 642013A GB 9300/48 A GB9300/48 A GB 9300/48A GB 930048 A GB930048 A GB 930048A GB 642013 A GB642013 A GB 642013A
- Authority
- GB
- United Kingdom
- Prior art keywords
- group
- chloride
- sulphonamide
- product
- isopropoxybenzoyl
- 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.)
- Expired
Links
- 150000003839 salts Chemical class 0.000 title abstract 2
- 150000003456 sulfonamides Chemical class 0.000 title abstract 2
- 238000004519 manufacturing process Methods 0.000 title 1
- 238000000034 method Methods 0.000 title 1
- 239000000047 product Substances 0.000 abstract 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 6
- USRKDQLKRQMYKX-UHFFFAOYSA-N 4-propan-2-yloxybenzoyl chloride Chemical compound CC(C)OC1=CC=C(C(Cl)=O)C=C1 USRKDQLKRQMYKX-UHFFFAOYSA-N 0.000 abstract 5
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 abstract 5
- 125000003277 amino group Chemical group 0.000 abstract 5
- QWKKYJLAUWFPDB-UHFFFAOYSA-N 4-nitrobenzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=C([N+]([O-])=O)C=C1 QWKKYJLAUWFPDB-UHFFFAOYSA-N 0.000 abstract 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 abstract 4
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 abstract 4
- FDDDEECHVMSUSB-UHFFFAOYSA-N sulfanilamide Chemical compound NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 abstract 4
- 229940124530 sulfonamide Drugs 0.000 abstract 4
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 abstract 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 3
- FBFBRAFXKGRRHI-UHFFFAOYSA-N n-(4-aminophenyl)sulfonyl-4-propan-2-yloxybenzamide Chemical compound C1=CC(OC(C)C)=CC=C1C(=O)NS(=O)(=O)C1=CC=C(N)C=C1 FBFBRAFXKGRRHI-UHFFFAOYSA-N 0.000 abstract 3
- JXRGUPLJCCDGKG-UHFFFAOYSA-N 4-nitrobenzenesulfonyl chloride Chemical compound [O-][N+](=O)C1=CC=C(S(Cl)(=O)=O)C=C1 JXRGUPLJCCDGKG-UHFFFAOYSA-N 0.000 abstract 2
- CFBLSYXKTPNMCD-UHFFFAOYSA-N 4-propan-2-yloxybenzamide Chemical compound CC(C)OC1=CC=C(C(N)=O)C=C1 CFBLSYXKTPNMCD-UHFFFAOYSA-N 0.000 abstract 2
- MVYWQGWUWWEZQZ-UHFFFAOYSA-N 4-propan-2-yloxybenzenecarboximidamide Chemical compound CC(C)OC1=CC=C(C(N)=N)C=C1 MVYWQGWUWWEZQZ-UHFFFAOYSA-N 0.000 abstract 2
- ZVERWTXKKWSSHH-UHFFFAOYSA-N 4-propan-2-yloxybenzoic acid Chemical compound CC(C)OC1=CC=C(C(O)=O)C=C1 ZVERWTXKKWSSHH-UHFFFAOYSA-N 0.000 abstract 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 abstract 2
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical class NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 abstract 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 abstract 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 abstract 2
- -1 benzene-sulphonyl halide Chemical class 0.000 abstract 2
- 235000014113 dietary fatty acids Nutrition 0.000 abstract 2
- 229930195729 fatty acid Natural products 0.000 abstract 2
- 239000000194 fatty acid Substances 0.000 abstract 2
- 150000004665 fatty acids Chemical class 0.000 abstract 2
- 150000007529 inorganic bases Chemical class 0.000 abstract 2
- 229910052742 iron Inorganic materials 0.000 abstract 2
- 150000007530 organic bases Chemical class 0.000 abstract 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract 2
- BMNDNPMJFWNHCX-UHFFFAOYSA-N 2-(2-iminoethoxy)ethanimine Chemical compound N=CCOCC=N BMNDNPMJFWNHCX-UHFFFAOYSA-N 0.000 abstract 1
- MNTBPUJZYKDEEW-UHFFFAOYSA-N 4-propan-2-yloxybenzenecarboximidamide;hydrochloride Chemical compound Cl.CC(C)OC1=CC=C(C(N)=N)C=C1 MNTBPUJZYKDEEW-UHFFFAOYSA-N 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- 229910021578 Iron(III) chloride Inorganic materials 0.000 abstract 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 abstract 1
- 229910006069 SO3H Inorganic materials 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 125000004442 acylamino group Chemical group 0.000 abstract 1
- 230000001476 alcoholic effect Effects 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000004104 aryloxy group Chemical group 0.000 abstract 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical class OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 abstract 1
- 159000000007 calcium salts Chemical class 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 abstract 1
- YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 abstract 1
- 239000003995 emulsifying agent Substances 0.000 abstract 1
- 230000001804 emulsifying effect Effects 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 230000003301 hydrolyzing effect Effects 0.000 abstract 1
- 239000013067 intermediate product Substances 0.000 abstract 1
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 abstract 1
- 150000002736 metal compounds Chemical class 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- JQWKTXIPRZXRJP-UHFFFAOYSA-N methyl n-(4-sulfamoylphenyl)carbamate Chemical compound COC(=O)NC1=CC=C(S(N)(=O)=O)C=C1 JQWKTXIPRZXRJP-UHFFFAOYSA-N 0.000 abstract 1
- PKOFBDHYTMYVGJ-UHFFFAOYSA-N n-(4-sulfamoylphenyl)acetamide Chemical compound CC(=O)NC1=CC=C(S(N)(=O)=O)C=C1 PKOFBDHYTMYVGJ-UHFFFAOYSA-N 0.000 abstract 1
- 229910052759 nickel Inorganic materials 0.000 abstract 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 abstract 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 abstract 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 abstract 1
- 159000000000 sodium salts Chemical class 0.000 abstract 1
- 239000000725 suspension Substances 0.000 abstract 1
- 238000005406 washing Methods 0.000 abstract 1
- 239000000080 wetting agent Substances 0.000 abstract 1
- 239000008096 xylene Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/30—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/45—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups at least one of the singly-bound nitrogen atoms being part of any of the groups, X being a hetero atom, Y being any atom, e.g. N-acylaminosulfonamides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Abstract
An acylated sulphonamide of the formula <FORM:0642013/IV (b)/1> is prepared by (a) acylating a sulphonamide of the formula <FORM:0642013/IV (b)/2> with p-isopropoxybenzoic acid or with a reactive derivative thereof, and converting the group R1 to an amino group, (2) condensing a benzene-sulphonyl halide of formula R1-C6H4-SO2-Hal with a metal compound of p-isopropoxybenzamide, and converting the group R1 to an amino group, or (3) condensing a reactive derivative of benzenesulphonic acid of the formula R1-C6H4-SO3H with a p-isopropoxy benziminoether or a p-isopropoxybenzamidine of the general formula <FORM:0642013/IV (b)/3> to give a product of formula <FORM:0642013/IV (b)/4> and then hydrolysing the group -N = CR2-to a -NH-CO- group and converting the group R1 to an amino group. In the above formul R1 is a nitrogen-containing group convertible to an amino group, e.g. an acylamino, nitro, p-benzeneazo or p-benzeneazoxy group, and R2 is an alkoxy, aryloxy or amino group. Salts of the new sulphonamide may be prepared, e.g. with inorganic or organic bases, several of which are specified. The p-amino groups in the sulphonamide may be acylated with high molecular fatty acids to produce capillary active products. In examples: (1) p-isopropoxy-benzoyl chloride and p-nitrobenzenesulphonamide are refluxed in the presence of chlorobenzene and copper powder (or ferric chloride or aluminium chloride) and the product reduced with iron filings and acetic acid; alternatively the intermediate product may be obtained by condensing p-isopropoxybenzoic acid with p-nitrobenzenesulphonamide in the presence of phosphorus pentachloride or pentoxide; (2) p-isopropoxybenzoyl chloride is refluxed with p-carbomethoxyamino - benzene - sulphonamide, chlorobenzene and copper powder and the product saponified to give N1-(4-isopropoxybenzoyl)-p-aminobenzenesulphonamide which is then converted to its calcium salt; (3) p-isopropoxybenzoyl chloride, p-acetylaminobenzenesulphonamide, nitrobenzene and copper powder are heated together and the product hydrolysed; (4) p-isopropoxybenzoyl chloride is added to p-nitrobenzenesulphonamide in pyridine or other acid-binding medium, and the product reduced with iron powder, hydrochloric acid and alcohol; (5) 4-isopropoxybenzoyl chloride is added to the sodium salt of p-nitrobenzenesulphonamide in nitrobenzene and the product reduced with iron and acetic acid; (6) p-nitrobenzenesulphonyl chloride in xylene is added to p-isopropoxybenzamide which has been heated with sodium amide, and the product is reduced with nickel and hydrogen; (7) p-nitrobenzenesulphonyl chloride is added to a suspension of p-isopropoxybenzamidine hydrochloride in pyridine, the product reduced, and the N - (4 - aminobenzenesulphonyl) - 41 - isopropoxybenzamidine obtained is hydrolysed with dilute hydrochloric acid; instead of p-isopropoxybenzamidine the corresponding imino-ethyl ether may be employed; (8) the ethylenediamine salt of N1-(4-isopropoxybenzoyl)-p-aminobenzenesulphonamide is prepared by adding ethylenediamine to an absolute methyl alcoholic solution of the sulphonamide; other organic or inorganic bases, e.g. diethylamine and ethylamine, may be used similarly. Specification 560,661 is referred to.ALSO:Capillary active products suitable for use as washing, emulsifying or wetting agents are obtained by acylating with high molecular fatty acids the p-amino group in the compound N1 - (4 - isopropoxybenzoyl) - p - aminobenzenesulphonamide.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH642013X | 1947-04-03 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB642013A true GB642013A (en) | 1950-08-23 |
Family
ID=4525498
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB9300/48A Expired GB642013A (en) | 1947-04-03 | 1948-04-02 | Process for the manufacture of a new acylated sulphonamide, and of its salts |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB642013A (en) |
-
1948
- 1948-04-02 GB GB9300/48A patent/GB642013A/en not_active Expired
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