DE4103393C2 - - Google Patents
Info
- Publication number
- DE4103393C2 DE4103393C2 DE19914103393 DE4103393A DE4103393C2 DE 4103393 C2 DE4103393 C2 DE 4103393C2 DE 19914103393 DE19914103393 DE 19914103393 DE 4103393 A DE4103393 A DE 4103393A DE 4103393 C2 DE4103393 C2 DE 4103393C2
- Authority
- DE
- Germany
- Prior art keywords
- water
- weight
- hour
- acid
- neutralized
- 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 - Fee Related
Links
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 14
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 12
- WVAKABMNNSMCDK-UHFFFAOYSA-N sulfacarbamide Chemical compound NC(=O)NS(=O)(=O)C1=CC=C(N)C=C1 WVAKABMNNSMCDK-UHFFFAOYSA-N 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 4
- 238000003756 stirring Methods 0.000 claims description 4
- 230000006196 deacetylation Effects 0.000 claims description 3
- 238000003381 deacetylation reaction Methods 0.000 claims description 3
- 150000007522 mineralic acids Chemical class 0.000 claims description 3
- XCSGUMXBOFCZJC-UHFFFAOYSA-N n-[4-(carbamoylsulfamoyl)phenyl]acetamide Chemical compound CC(=O)NC1=CC=C(S(=O)(=O)NC(N)=O)C=C1 XCSGUMXBOFCZJC-UHFFFAOYSA-N 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims 1
- 239000000047 product Substances 0.000 description 7
- 239000000243 solution Substances 0.000 description 4
- 229940124530 sulfonamide Drugs 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 229930000044 secondary metabolite Natural products 0.000 description 3
- FDDDEECHVMSUSB-UHFFFAOYSA-N sulfanilamide Chemical compound NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 description 3
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 239000012670 alkaline solution Substances 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 239000004202 carbamide Substances 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- WVBFNSJUEUADMP-UHFFFAOYSA-N 4-acetyl-4-aminocyclohexa-1,5-diene-1-sulfonamide Chemical compound CC(=O)C1(N)CC=C(S(N)(=O)=O)C=C1 WVBFNSJUEUADMP-UHFFFAOYSA-N 0.000 description 1
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 1
- 230000021736 acetylation Effects 0.000 description 1
- 238000006640 acetylation reaction Methods 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000008092 positive effect Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/36—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of amides of sulfonic acids
- C07C303/40—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of amides of sulfonic acids by reactions not involving the formation of sulfonamide groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19914103393 DE4103393A1 (de) | 1991-02-05 | 1991-02-05 | Verfahren zur herstellung von kristallinem p-aminophenylsulfonylharnstoff |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19914103393 DE4103393A1 (de) | 1991-02-05 | 1991-02-05 | Verfahren zur herstellung von kristallinem p-aminophenylsulfonylharnstoff |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE4103393A1 DE4103393A1 (de) | 1992-08-06 |
| DE4103393C2 true DE4103393C2 (enrdf_load_html_response) | 1993-07-08 |
Family
ID=6424395
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19914103393 Granted DE4103393A1 (de) | 1991-02-05 | 1991-02-05 | Verfahren zur herstellung von kristallinem p-aminophenylsulfonylharnstoff |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE4103393A1 (enrdf_load_html_response) |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2411661A (en) * | 1939-12-23 | 1946-11-26 | Geigy Ag J R | 4-aminobenzene-sulfone-carbamic acid derivative |
-
1991
- 1991-02-05 DE DE19914103393 patent/DE4103393A1/de active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| DE4103393A1 (de) | 1992-08-06 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OP8 | Request for examination as to paragraph 44 patent law | ||
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |