GB602934A - Manufacture of aromatic acyl-sulphonamides - Google Patents
Manufacture of aromatic acyl-sulphonamidesInfo
- Publication number
- GB602934A GB602934A GB2804545A GB2804545A GB602934A GB 602934 A GB602934 A GB 602934A GB 2804545 A GB2804545 A GB 2804545A GB 2804545 A GB2804545 A GB 2804545A GB 602934 A GB602934 A GB 602934A
- Authority
- GB
- United Kingdom
- Prior art keywords
- sulphonamide
- benzene
- heating
- toluene
- naphthoyl
- 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 1
- 238000004519 manufacturing process Methods 0.000 title 1
- 238000010438 heat treatment Methods 0.000 abstract 6
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 abstract 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 5
- KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 abstract 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 2
- 125000003545 alkoxy group Chemical group 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 125000004414 alkyl thio 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
- -1 aromatic carboxylic acids Chemical class 0.000 abstract 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 abstract 2
- 229910052736 halogen Chemical group 0.000 abstract 2
- 150000002367 halogens Chemical group 0.000 abstract 2
- 159000000000 sodium salts Chemical class 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
- LKGIATHYPPEJEL-UHFFFAOYSA-N 2,2-diphenyl-N-(2,3,5,6-tetramethylphenyl)sulfonylacetamide Chemical compound C1(=CC=CC=C1)C(C(=O)NS(=O)(=O)C=1C(=C(C)C=C(C=1C)C)C)C1=CC=CC=C1 LKGIATHYPPEJEL-UHFFFAOYSA-N 0.000 abstract 1
- WOTPIPCWLVBYSQ-UHFFFAOYSA-N 2,3,5,6-tetramethylbenzenesulfonamide Chemical compound CC1=CC(C)=C(C)C(S(N)(=O)=O)=C1C WOTPIPCWLVBYSQ-UHFFFAOYSA-N 0.000 abstract 1
- WBJWXIQDBDZMAW-UHFFFAOYSA-N 2-hydroxynaphthalene-1-carbonyl chloride Chemical compound C1=CC=CC2=C(C(Cl)=O)C(O)=CC=C21 WBJWXIQDBDZMAW-UHFFFAOYSA-N 0.000 abstract 1
- HSPZFYZBTVVAOC-UHFFFAOYSA-N 3,4-dimethylbenzenesulfonamide Chemical compound CC1=CC=C(S(N)(=O)=O)C=C1C HSPZFYZBTVVAOC-UHFFFAOYSA-N 0.000 abstract 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 abstract 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 abstract 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 abstract 1
- PYHXGXCGESYPCW-UHFFFAOYSA-N alpha-phenylbenzeneacetic acid Natural products C=1C=CC=CC=1C(C(=O)O)C1=CC=CC=C1 PYHXGXCGESYPCW-UHFFFAOYSA-N 0.000 abstract 1
- 150000001408 amides Chemical class 0.000 abstract 1
- 159000000032 aromatic acids Chemical class 0.000 abstract 1
- 150000001735 carboxylic acids Chemical class 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
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- FDDDEECHVMSUSB-UHFFFAOYSA-N sulfanilamide Chemical compound NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 abstract 1
- 229940124530 sulfonamide Drugs 0.000 abstract 1
- XTHPWXDJESJLNJ-UHFFFAOYSA-N sulfurochloridic acid Chemical compound OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 abstract 1
- LMYRWZFENFIFIT-UHFFFAOYSA-N toluene-4-sulfonamide Chemical compound CC1=CC=C(S(N)(=O)=O)C=C1 LMYRWZFENFIFIT-UHFFFAOYSA-N 0.000 abstract 1
- 239000008096 xylene Substances 0.000 abstract 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Acyl-sulphonamides are made by reacting a benzene sulphonamide, in which the benzene radical may be substituted by alkyl, alkoxy, alkylmercapto groups and/or halogen, with araliphatic or condensed aromatic carboxylic acids or their functional derivatives. In a modification, benzene sulphohalide, which may be substituted by alkyl, alkoxy, alkylmercapto groups and/or halogen, are reacted with salts of amides of araliphatic or of condensed aromatic carboxylic acids. In examples: (1) N-(a -naphthoyl)-benzene sulphonamide is made by heating benzene sulphonamide and a -naphthoyl chloride in pyridine, or by heating the sodium salt of benzene sulphonamide with a - naphthoyl chloride or bromide in nitrobenzene; (2) N-(a a -dimethyl-phenacetyl)-p-toluene sulphonamide is made by heating p-toluene sulphochloride and the sodium salt of a a -dimethyl-phenacetamide in xylene; (3) N-(b -naphthoyl)-3,4-dimethylbenzene sulphonamide is made by heating 3,4-dimethylbenzene sulphonamide and b -naphthoic acid chloride with aluminium chloride in nitrobenzene; (4) N - (b -phenyl-cinnamoyl) - p - toluene sulphonamide is made by heating p-toluene sulphonamide and b -phenyl-cinnamic acid with phosphorus pentoxide in chlorobenzene; and (5) N - (diphenyl - acetyl) - durene sulphonamide is made by heating durene sulphonamide and diphenyl-acetic acid with phosphorus pentachloride in nitrobenzene. Many other suitable substituted benzene sulphonamides, araliphatic carboxylic acids and condensed aromatic acids are specified.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2804545A GB602934A (en) | 1945-10-24 | 1945-10-24 | Manufacture of aromatic acyl-sulphonamides |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2804545A GB602934A (en) | 1945-10-24 | 1945-10-24 | Manufacture of aromatic acyl-sulphonamides |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB602934A true GB602934A (en) | 1948-06-07 |
Family
ID=10269366
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2804545A Expired GB602934A (en) | 1945-10-24 | 1945-10-24 | Manufacture of aromatic acyl-sulphonamides |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB602934A (en) |
-
1945
- 1945-10-24 GB GB2804545A patent/GB602934A/en not_active Expired
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