GB578564A - Manufacture of p-aminobenzene sulphonic acid amides - Google Patents
Manufacture of p-aminobenzene sulphonic acid amidesInfo
- Publication number
- GB578564A GB578564A GB6551/44A GB655144A GB578564A GB 578564 A GB578564 A GB 578564A GB 6551/44 A GB6551/44 A GB 6551/44A GB 655144 A GB655144 A GB 655144A GB 578564 A GB578564 A GB 578564A
- Authority
- GB
- United Kingdom
- Prior art keywords
- acid
- amide
- sulphonamide
- treated
- chloride
- 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
- FDDDEECHVMSUSB-UHFFFAOYSA-N sulfanilamide Chemical class NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 title abstract 4
- 238000004519 manufacturing process Methods 0.000 title 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 6
- 229940124530 sulfonamide Drugs 0.000 abstract 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 abstract 3
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 abstract 3
- 159000000000 sodium salts Chemical class 0.000 abstract 3
- 239000008096 xylene Substances 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
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 abstract 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract 2
- -1 araliphatic Chemical group 0.000 abstract 2
- 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
- 239000007868 Raney catalyst Substances 0.000 abstract 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 abstract 1
- 229910000564 Raney nickel Inorganic materials 0.000 abstract 1
- 125000001931 aliphatic group Chemical group 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 238000010531 catalytic reduction reaction Methods 0.000 abstract 1
- 238000009833 condensation Methods 0.000 abstract 1
- 230000005494 condensation Effects 0.000 abstract 1
- QIJQSTNYYPTNBF-UHFFFAOYSA-N ethyl n-(4-chlorosulfonylphenyl)carbamate Chemical compound CCOC(=O)NC1=CC=C(S(Cl)(=O)=O)C=C1 QIJQSTNYYPTNBF-UHFFFAOYSA-N 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 230000007062 hydrolysis Effects 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 1
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 abstract 1
- HKTBRYQNVRPBCF-UHFFFAOYSA-N nitrobenzene;sulfurochloridic acid Chemical compound OS(Cl)(=O)=O.[O-][N+](=O)C1=CC=CC=C1 HKTBRYQNVRPBCF-UHFFFAOYSA-N 0.000 abstract 1
- IBBMAWULFFBRKK-UHFFFAOYSA-N picolinamide Chemical compound NC(=O)C1=CC=CC=N1 IBBMAWULFFBRKK-UHFFFAOYSA-N 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- 239000000376 reactant Substances 0.000 abstract 1
- 239000011541 reaction mixture Substances 0.000 abstract 1
- 238000006722 reduction reaction Methods 0.000 abstract 1
- 238000010992 reflux Methods 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 235000011121 sodium hydroxide Nutrition 0.000 abstract 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
p-Aminobenzene sulphonic acid amides are produced by the condensation of a p-nitro-, or a p-acylamino-benzene sulphonic acid halide with a salt of an aliphatic, araliphatic, aromatic hydroaromatic or heterocyclic carboxylic acid amide followed by reduction or hydrolysis as necessary to form the primary amino group. In examples: (1) Powdered sodium amide is added to a xylene solution of 3 : 4-dimethylbenzamide, and the reactants then treated with p-nitrobenzenesulphonic acid chloride. The 4 - nitrobenzene - N - (31 : 41 - dimethylbenzoyl) sulphonamide is reduced by catalytic reduction with Raney nickel to the corresponding p-amino compound. (2) b b -dimethylacrylic acid amide is converted into its sodium salt with sodium amide and treated with p-nitrobenzenesulphonic acid chloride as in example (1) to form 4-nitrobenzene-N-(b b -dimethylacroyl)-sulphonamide, which is then reduced with iron powder and acetic acid. (3) b b -dimethylacrylic acid amide is converted into its sodium salt as in example (1) and treated with acetylsulphonilic acid chloride to form 4-(N-acetylamino)-N1-b b -dimethylacroyl-sulphonamide which is then saponified. (4) 3 : 4 - dimethyl - benzamide is converted into its sodium salt as in example (1) and then treated with N-carbethoxysulphanilic acid chloride to form 4-(N-carbethoxyaminobenzene)-N1-(31 : 41-dimethylbenzoyl) sulphonamide, which is then saponified with dilute soda lye on the water bath. A sample has been filed under Sect. 2 (5) of the Acts of 4-aminobenzene-N1-picolyl sulphonic acid amide prepared by adding sodium amide to a solution of picolinic acid amide in xylene followed by a xylene solution of p-nitrobenzene sulpho-chloride, and heating the reaction mixture under reflux. The nitro group is then reduced according to the method of Bechamp with iron powder and acetic acid.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH578564X | 1943-04-09 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB578564A true GB578564A (en) | 1946-07-03 |
Family
ID=4521353
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB6551/44A Expired GB578564A (en) | 1943-04-09 | 1944-04-07 | Manufacture of p-aminobenzene sulphonic acid amides |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB578564A (en) |
-
1944
- 1944-04-07 GB GB6551/44A patent/GB578564A/en not_active Expired
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