CH215335A - Process for the preparation of phthalimide-4-sulfophenylamide. - Google Patents
Process for the preparation of phthalimide-4-sulfophenylamide.Info
- Publication number
- CH215335A CH215335A CH215335DA CH215335A CH 215335 A CH215335 A CH 215335A CH 215335D A CH215335D A CH 215335DA CH 215335 A CH215335 A CH 215335A
- Authority
- CH
- Switzerland
- Prior art keywords
- sep
- sulfophenylamide
- phthalimide
- acid
- parts
- Prior art date
Links
- -1 phthalimide-4-sulfophenylamide Chemical compound 0.000 title claims description 9
- 238000000034 method Methods 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title description 3
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 6
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 claims description 4
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 claims description 4
- XRXMNWGCKISMOH-UHFFFAOYSA-N 2-bromobenzoic acid Chemical compound OC(=O)C1=CC=CC=C1Br XRXMNWGCKISMOH-UHFFFAOYSA-N 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 3
- DOBRDRYODQBAMW-UHFFFAOYSA-N copper(i) cyanide Chemical compound [Cu+].N#[C-] DOBRDRYODQBAMW-UHFFFAOYSA-N 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 239000000155 melt Substances 0.000 claims description 3
- 239000000975 dye Substances 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims description 2
- 229940126601 medicinal product Drugs 0.000 claims 1
- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 claims 1
- 239000007858 starting material Substances 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 229940124530 sulfonamide Drugs 0.000 description 2
- IKCLCGXPQILATA-UHFFFAOYSA-N 2-chlorobenzoic acid Chemical compound OC(=O)C1=CC=CC=C1Cl IKCLCGXPQILATA-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
Landscapes
- Indole Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung von Phthalimid-4-sulfophenylamid. Im Hauptpatent ist ein Verfahren zur Herstellung von Phthalimid-4-sulfonamid be schrieben, bei dem man 2-Chlorbenzoesäure mit Chlorsulfonsäure in das 2-Chlorbenzoe- 5 säure-5-sulfochlorid überführt, dieses mit Ammoniak behandelt und das erhaltene 2- Chlorbenzoesäure-5-sulfonamid mit Kupfer (1)-cyanid erhitzt.
Es wurde nun gefunden, dass man Phthal- imid-4-sulfophenylamid erhält, wenn man 2-Brombenzoe.säure mit Chlorsulfonsäure in das 2-Brombenzoesäure-5-sulfochlorid über führt, dieses mit Anilin behandelt und das erhaltene 2-Brombenzoesäure-5-sulfophenyl- amid mit Kupfer(1)-cyanid erhitzt.
Die Umsetzung vollzieht sich nach fol genden Formeln:
EMI0001.0023
Dabei ist es im allgemeinen nicht nötig, jede einzelne Zwischenverbindung als solche abzutrennen; meistens kann man zwei oder mehrere Umsetzungsstufen in einem Arbeits gang vereinigen. Das Phthalimid-4-sulfophenylamid ist eine bei 199 C schmelzende farblose Sub stanz, die neu ist und zur Herstellung von Heilmitteln und Farbstoffen Verwendung findet.
Reisbiel: 590 Teile 2-Brombenzoesäure-5-sulfo- chlorid (hergestellt aus 2-Brombenzoesä,ure und Chlorsulfonsäure analog der im Beispiel des Hauptpatentes gegebenen Vorschrift) werden in eine 40 bis 50 C warme 31isehung von 2150 Teilen Wasser, 200 Teilen Anilin und 300 Teilen kristallisiertem Natrium acetat eingetragen. Diese 11ischung wird etwa 3 bis 4 Stunden lang bei 40 bis 50 C gerührt.
Nach dem Erkalten wird das aus geschiedene 2 - Brombenzoesäure - 5 - sulfo- phenylamid abgesaugt, einige Male mit Was ser gewaschen und dann getrocknet.
285 Teile der so erhaltenen Verbindung werden zusammen mit 1500 Teilen o-Diehlor- benzol, 70 Teilen Pyridin imd 79 Teilen gupfer(1)-eyanid etwa l1" Stunden lang auf 170 bis 175 C erhitzt.
Nach dem Ab= destillieren des Verdünnungsmittels mit Wasserdampf wird der Rückstand abgesaugt. mit starker Salzsäure gewaschen, bis er kein Kupfer mehr enthält, und dann mit Wasser
EMI0002.0019
neutral <SEP> gewaschen. <SEP> Man <SEP> erhalt <SEP> so <SEP> mit <SEP> nahezu
<tb> der <SEP> berechneten <SEP> Ausbeute <SEP> das <SEP> Phthalimid-4 sulfophenylamid, <SEP> das <SEP> nach <SEP> dein <SEP> Umkristalli sieren <SEP> aus <SEP> o-Dichlorbenzol <SEP> bei <SEP> <B>199</B> <SEP> <SEP> C
<tb> schmilzt.
Process for the preparation of phthalimide-4-sulfophenylamide. In the main patent, a process for the preparation of phthalimide-4-sulfonamide is described in which 2-chlorobenzoic acid is converted with chlorosulfonic acid into 2-chlorobenzoic acid-5-sulfochloride, this is treated with ammonia and the 2-chlorobenzoic acid-5 obtained -sulfonamide heated with copper (1) cyanide.
It has now been found that phthalimide-4-sulfophenylamide is obtained if 2-bromobenzoic acid is converted into 2-bromobenzoic acid-5-sulfochloride with chlorosulfonic acid, this is treated with aniline and the 2-bromobenzoic acid-5- sulfophenyl amide heated with copper (1) cyanide.
The implementation takes place according to the following formulas:
EMI0001.0023
It is generally not necessary to separate each individual intermediate compound as such; in most cases, you can combine two or more implementation stages in one operation. The phthalimide-4-sulfophenylamide is a colorless substance that melts at 199 C, is new and is used in the manufacture of medicines and dyes.
Reisbiel: 590 parts of 2-bromobenzoic acid-5-sulfochloride (prepared from 2-bromobenzoic acid and chlorosulfonic acid analogously to the instructions given in the example of the main patent) are in a 40 to 50 C warm 31isehung of 2150 parts of water, 200 parts of aniline and 300 parts of crystallized sodium acetate entered. This mixture is stirred at 40 to 50 ° C. for about 3 to 4 hours.
After cooling, the separated 2 - bromobenzoic acid - 5 - sulfophenylamide is filtered off with suction, washed a few times with water and then dried.
285 parts of the compound thus obtained are heated to 170-175 ° C. for about 11 "hours together with 1500 parts of o-diehlorbenzene, 70 parts of pyridine and 79 parts of gupfer (1) yanide.
After the diluent has been distilled off with steam, the residue is filtered off with suction. washed with strong hydrochloric acid until it no longer contains copper, and then with water
EMI0002.0019
washed neutral <SEP>. <SEP> You <SEP> almost get <SEP> like <SEP> with <SEP>
<tb> the <SEP> calculated <SEP> yield <SEP> the <SEP> phthalimide-4 sulfophenylamide, <SEP> the <SEP> after <SEP> your <SEP> recrystallization <SEP> from <SEP> o- Dichlorobenzene <SEP> at <SEP> <B> 199 </B> <SEP> <SEP> C
<tb> melts.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE215335X | 1938-02-15 | ||
| CH210091T | 1939-01-23 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH215335A true CH215335A (en) | 1941-06-15 |
Family
ID=25724776
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH215335D CH215335A (en) | 1938-02-15 | 1939-01-23 | Process for the preparation of phthalimide-4-sulfophenylamide. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH215335A (en) |
-
1939
- 1939-01-23 CH CH215335D patent/CH215335A/en unknown
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