US2417004A - Process for the manufacture of 4-aminobenzene-nu1-(3':4'-dimethylbenzoyl)-sulfonamide - Google Patents
Process for the manufacture of 4-aminobenzene-nu1-(3':4'-dimethylbenzoyl)-sulfonamide Download PDFInfo
- Publication number
- US2417004A US2417004A US528340A US52834044A US2417004A US 2417004 A US2417004 A US 2417004A US 528340 A US528340 A US 528340A US 52834044 A US52834044 A US 52834044A US 2417004 A US2417004 A US 2417004A
- Authority
- US
- United States
- Prior art keywords
- sulfonamide
- dimethylbenzoyl
- nitrobenzene
- manufacture
- aminobenzene
- 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 - Lifetime
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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
Definitions
- Example 1 part of 3:4-dimethyl benzamide is dissolved at 30-40 C. in parts of absolute pyridine and slowly heated with .1 part of 4-nitrobenzene-sulfene chloride. After a short heating on .the water-bath the mixture is poured into ice-cold diluted hydrochloric acid. The precipitation thus separated is filtered, dried and recrystallised from absolute benzene. Thus colorless prisms are obtained, the same havingthe melting point of 158 C.
- the oxidation can also be performed with hydrogen peroxide instead of potassium permanganate.
- a process for the manufacture of 4-nitrobenzene N1 (3' :4 dimethylbenzoyl)-su1fonamide which comprises subjecting 4-nitrobenzene- N1-(3 :4-dimethylbenzoyl) -sulfenamide to the action of an oxidizing agent whereby the corresponding sulfonamide is obtained, and then subjecting the resultant 4-nitrobenzene-N1-(3:4- dimethylbenzoyl) -sulfonamide to the action of a reducing agent whereby the nitro group is reduced to amino.
Description
Patented Mar. 4, 1947 PROCESS FOR THE MANUFACTURE OF 4- AlVIINOBENZENE-N (3:4'-DIMETHYLBEN- ZOYL) SULFONAMIDE Henry Martin and Otto Neracher, Basel, Switzerland, assignors to the firm of J. R. Geigy A. G.,
Basel, Switzerland No Drawing. Application March 27, 1944, Serial No. 528,340. In Switzerland April 9, 1943 4 Claims.
The condensation of p-nitrobenzene sulfene chloride with acetamide and subsequent oxidation of the acetylated p-nitrobenzene sulfenamide to p-nitrobenzene sulfone acetamide is known.
However, the same interaction cannot be carried out with tetramethyl benzamide, the arcmatic acids, which are rich in alkyl groups, being largely decomposed and destroyed on oxidation.
Surprisingly we have now found that the oxidation of p-nitrobenzene-Ni- (3' :4-dimethy1benzoyl) -su1fenamide can nevertheless be carried out. Of course this fact could not be presumed.
The invention i illustrated, but not limited by the following example, wherein the parts are by weight.
Example 1 part of 3:4-dimethyl benzamide is dissolved at 30-40 C. in parts of absolute pyridine and slowly heated with .1 part of 4-nitrobenzene-sulfene chloride. After a short heating on .the water-bath the mixture is poured into ice-cold diluted hydrochloric acid. The precipitation thus separated is filtered, dried and recrystallised from absolute benzene. Thus colorless prisms are obtained, the same havingthe melting point of 158 C.
1 part of 4-nitrobenzene-N1-(3z4' dimethylbenzoyD-sulfenamide is dissolved in 50 parts of acetone and, while stirring, dropwise treated at room temperature with a 3% potassium per manganate solution in acetone, until the red coloration remains unchanged. Then there is rapidly sucked oil and the 4-nitrobenzene-N1-(3' :4- dimethylbenzoyll-sulfamide melting at 192 C. is recovered by concentration of the acetone solution. By reduction it can be converted into paminobenzene-sulfone-3 4-dimethy1 benzamide.
The oxidation can also be performed with hydrogen peroxide instead of potassium permanganate.
- Number What we claim is:
1. In a process for the manufacture of 4-aminobenZene-N1-(3' :4-dimethylbenzoyl) sulfonamide, the step which consists in subjecting 4- nitrobenzene-N1-(3 :4-dimethy1benzoyl) -sulfenamide to the action of an oxidizing agent whereby the corresponding sulfonamide is obtained.
2. In a process for the manufacture of 4-aminobenzene-N1-(3' :4 -dimethy1benzoyl) sulfonamide, the step which consists in subjecting 4-nitrobenzene N1 (3' :4-dimethylbenzoyl) -sulfenamide to the action of potassium permanganate whereby the corresponding sulfonamide is obtained.
3. In a process for the manufacture of 4-aminobenzene-N1-(3 :4-dimethylbenzoyl) sulfonamide, the step which consists in subjecting 4-nitrobenzene-N1-(3' :4-dimethylbenzoyl) sulfenamide to the action of hydrogen peroxide whereby the corresponding sulfonamide is obtained.
4. A process for the manufacture of 4-nitrobenzene N1 (3' :4 dimethylbenzoyl)-su1fonamide, which comprises subjecting 4-nitrobenzene- N1-(3 :4-dimethylbenzoyl) -sulfenamide to the action of an oxidizing agent whereby the corresponding sulfonamide is obtained, and then subjecting the resultant 4-nitrobenzene-N1-(3:4- dimethylbenzoyl) -sulfonamide to the action of a reducing agent whereby the nitro group is reduced to amino.
HENRY MARTIN. OTTO NERACHER.
REFERENCES CITED The following references are of record in the file of this patent:
FOREIGN PATENTS Country Date 551,207 British 1942
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH2417004X | 1943-04-09 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2417004A true US2417004A (en) | 1947-03-04 |
Family
ID=4569122
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US528340A Expired - Lifetime US2417004A (en) | 1943-04-09 | 1944-03-27 | Process for the manufacture of 4-aminobenzene-nu1-(3':4'-dimethylbenzoyl)-sulfonamide |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US2417004A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3180559A (en) * | 1962-04-11 | 1965-04-27 | John R Boyd | Mechanical vacuum pump |
| US3855262A (en) * | 1968-03-20 | 1974-12-17 | Monsanto Co | N-(hydrocarbylthio) amides |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB551207A (en) * | 1941-04-29 | 1943-02-11 | Manchester Oxide Co Ltd | Improvements in and relating to the manufacture of sulphonamido compounds |
-
1944
- 1944-03-27 US US528340A patent/US2417004A/en not_active Expired - Lifetime
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB551207A (en) * | 1941-04-29 | 1943-02-11 | Manchester Oxide Co Ltd | Improvements in and relating to the manufacture of sulphonamido compounds |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3180559A (en) * | 1962-04-11 | 1965-04-27 | John R Boyd | Mechanical vacuum pump |
| US3855262A (en) * | 1968-03-20 | 1974-12-17 | Monsanto Co | N-(hydrocarbylthio) amides |
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