GB602426A - Manufacture of aromatic acyl-sulphonamides - Google Patents
Manufacture of aromatic acyl-sulphonamidesInfo
- Publication number
- GB602426A GB602426A GB28046/45A GB2804645A GB602426A GB 602426 A GB602426 A GB 602426A GB 28046/45 A GB28046/45 A GB 28046/45A GB 2804645 A GB2804645 A GB 2804645A GB 602426 A GB602426 A GB 602426A
- Authority
- GB
- United Kingdom
- Prior art keywords
- naphthalene
- sulphonamide
- heating
- carboxylic acid
- sulphonamides
- 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
- 125000003118 aryl group Chemical group 0.000 title abstract 5
- 238000004519 manufacturing process Methods 0.000 title 1
- 229940124530 sulfonamide Drugs 0.000 abstract 7
- 238000010438 heat treatment Methods 0.000 abstract 6
- FDDDEECHVMSUSB-UHFFFAOYSA-N sulfanilamide Chemical compound NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 abstract 6
- 150000001735 carboxylic acids Chemical class 0.000 abstract 3
- 125000001931 aliphatic group Chemical group 0.000 abstract 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 abstract 2
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 abstract 2
- 125000000623 heterocyclic group Chemical group 0.000 abstract 2
- 125000001624 naphthyl group Chemical group 0.000 abstract 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 abstract 2
- DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 abstract 2
- WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 abstract 1
- YAHLWSGIQJATGG-UHFFFAOYSA-N 1-(4-chlorophenyl)cyclopropane-1-carboxylic acid Chemical compound C=1C=C(Cl)C=CC=1C1(C(=O)O)CC1 YAHLWSGIQJATGG-UHFFFAOYSA-N 0.000 abstract 1
- ICGNTMSBIYZZPY-UHFFFAOYSA-N 1-chloronaphthalene sulfurochloridic acid Chemical compound S(=O)(=O)(O)Cl.ClC1=CC=CC2=CC=CC=C12 ICGNTMSBIYZZPY-UHFFFAOYSA-N 0.000 abstract 1
- 125000001088 1-naphthoyl group Chemical group C1(=CC=CC2=CC=CC=C12)C(=O)* 0.000 abstract 1
- -1 1-propylcinnamoyl Chemical group 0.000 abstract 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 abstract 1
- XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 abstract 1
- WBYWAXJHAXSJNI-SREVYHEPSA-N Cinnamic acid Chemical compound OC(=O)\C=C/C1=CC=CC=C1 WBYWAXJHAXSJNI-SREVYHEPSA-N 0.000 abstract 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 abstract 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 abstract 1
- 150000001408 amides Chemical class 0.000 abstract 1
- 229930016911 cinnamic acid Natural products 0.000 abstract 1
- 235000013985 cinnamic acid Nutrition 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 abstract 1
- 230000004048 modification Effects 0.000 abstract 1
- 238000012986 modification Methods 0.000 abstract 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 159000000000 sodium salts Chemical class 0.000 abstract 1
- 150000003456 sulfonamides Chemical class 0.000 abstract 1
- 239000008096 xylene Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
- C07C2603/22—Ortho- or ortho- and peri-condensed systems containing three rings containing only six-membered rings
- C07C2603/24—Anthracenes; Hydrogenated anthracenes
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Acyl-sulphonamides are made by reacting naphthyl-, anthryl-, or phenanthryl-sulphonamides, which may contain non-saltforming groups in the nucleus, with aliphatic, cycloaliphatic, araliphatic, heterocyclic, substituted aromatic, or aromatic condensed ring carboxylic acids or their functional derivatives. In a modification, the naphthyl-, anthryl-, or phenanthryl-sulphohalides, which may be substituted by non-saltforming groups, are reacted with salts of amides of aliphatic, cycloaliphatic, araliphatic, heterocyclic substituted aromatic, or aromatic condensed ring carboxylic acids. In examples: (1) N - (b 1 - naphthoyl) - b - naphthalene sulphonamide is made by heating b -naphthalene sulphonamide with b -naphthalene carboxylic acid chloride in pyridine-in a similar reaction the a -naphthalene carboxylic acid chloride may be used instead of the b -naphthalene carboxylic acid chloride; (2) N-cinnamoyl-a -naphthalene sulphonamide is made by heating a -naphthalene sulphonamide with cinnamic acid chloide; (3) N-(g g g -trichlorocrotonyl) - a - naphthalene sulphonamide is made by heating a -naphthalene sulphonamide and g g g -trichlorocrotonic acid chloride with aluminium chloride or copper powder in nitrobenzene; (4) N - (a - phenyl - isovaleryl) - 4 - chloronaphthalene-2-sulphonamide is made by heating 4 - chloronaphthalene sulphochloride with the sodium salt of a -phenyl-isovaleric acid amide in xylene; (5) N-(a -naphthalenesulphonyl) - 1 - (p - chlorophenyl) - cyclopropane - 1 - carboxylic acid amide is made by heating a -naphthalene sulphonamide and 1-(p-chlorophenyl) - cyclopropane - 1 - carboxylic acid with phosphorus pentoxide in chlorobenzene- and in an analogous manner, N-(a -naphthalene - sulphonyl) - 1 - (31,41 - dimethylphenyl) - cyclopentane - 1 - carboxylic acid amide may be produced, and (6) N - (b 1-propylcinnamoyl) - b - naphthalene-sulphonamide is made by heating b -naphthalene-sulphonamide and b -propyl-cinnamic acid with phosphorus pentachloride in nitrobenzene-and in an analogous manner N-(2,5-dichlorobenzoyl)-b -naphthalene sulphonamide may be produced. Many other sulphonamides and carboxylic acids suitable for use in the process are specified.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB28046/45A GB602426A (en) | 1945-10-24 | 1945-10-24 | Manufacture of aromatic acyl-sulphonamides |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB28046/45A GB602426A (en) | 1945-10-24 | 1945-10-24 | Manufacture of aromatic acyl-sulphonamides |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB602426A true GB602426A (en) | 1948-05-26 |
Family
ID=10269384
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB28046/45A Expired GB602426A (en) | 1945-10-24 | 1945-10-24 | Manufacture of aromatic acyl-sulphonamides |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB602426A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7838537B2 (en) | 2003-01-22 | 2010-11-23 | Boehringer Ingelheim International Gmbh | Viral polymerase inhibitors |
| US7888363B2 (en) | 2003-01-22 | 2011-02-15 | Boehringer Ingelheim International Gmbh | Viral polymerase inhibitors |
| WO2019053634A1 (en) * | 2017-09-14 | 2019-03-21 | AbbVie S.à.r.l. | Modulators of the cystic fibrosis transmembrane conductance regulator protein and methods of use |
-
1945
- 1945-10-24 GB GB28046/45A patent/GB602426A/en not_active Expired
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7838537B2 (en) | 2003-01-22 | 2010-11-23 | Boehringer Ingelheim International Gmbh | Viral polymerase inhibitors |
| US7888363B2 (en) | 2003-01-22 | 2011-02-15 | Boehringer Ingelheim International Gmbh | Viral polymerase inhibitors |
| WO2019053634A1 (en) * | 2017-09-14 | 2019-03-21 | AbbVie S.à.r.l. | Modulators of the cystic fibrosis transmembrane conductance regulator protein and methods of use |
| EP3865474A1 (en) * | 2017-09-14 | 2021-08-18 | AbbVie Overseas S.à r.l. | Modulators of the cystic fibrosis transmembrane conductance regulator protein and methods of use |
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