CH205066A - Process for the preparation of chloroterephthaloyl-1- (4'-nitranilide) -4-chloride. - Google Patents
Process for the preparation of chloroterephthaloyl-1- (4'-nitranilide) -4-chloride.Info
- Publication number
- CH205066A CH205066A CH205066DA CH205066A CH 205066 A CH205066 A CH 205066A CH 205066D A CH205066D A CH 205066DA CH 205066 A CH205066 A CH 205066A
- Authority
- CH
- Switzerland
- Prior art keywords
- chloride
- chloroterephthaloyl
- nitranilide
- preparation
- acetone
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 5
- 238000002360 preparation method Methods 0.000 title description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 8
- 150000001875 compounds Chemical class 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 239000013078 crystal Substances 0.000 claims description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 2
- 239000011707 mineral Substances 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- TYMLOMAKGOJONV-UHFFFAOYSA-N 4-nitroaniline Chemical compound NC1=CC=C([N+]([O-])=O)C=C1 TYMLOMAKGOJONV-UHFFFAOYSA-N 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 238000001816 cooling Methods 0.000 description 2
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 2
- LNJUVOPKIUQOQK-UHFFFAOYSA-N (4-nitrophenyl)azanium;chloride Chemical compound Cl.NC1=CC=C([N+]([O-])=O)C=C1 LNJUVOPKIUQOQK-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- MSWAXXJAPIGEGZ-UHFFFAOYSA-N 2-chlorobenzene-1,4-dicarbonyl chloride Chemical compound ClC(=O)C1=CC=C(C(Cl)=O)C(Cl)=C1 MSWAXXJAPIGEGZ-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- -1 benzene and xylene Chemical class 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000004567 concrete Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 150000004820 halides Chemical group 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- VBEGHXKAFSLLGE-UHFFFAOYSA-N n-phenylnitramide Chemical compound [O-][N+](=O)NC1=CC=CC=C1 VBEGHXKAFSLLGE-UHFFFAOYSA-N 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 229940127557 pharmaceutical product Drugs 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/12—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by halogen atoms or by nitro or nitroso groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung von Chlorterephthaloyl-1-(4'-nitranilid)-4-chlorid. Gegenstand,des vorliegenden Zusatzpaten- tes ist ein Verfahren zur Herstellung von Chlorterephthaloyl-l-(4'-nitranilid)-4-chlorid, welches idaadurch gekennzeichnet ist, dass man auf ein Mol Chlorteiephthaloylchlorid in Ge- genwart von organischen Lösungsmitteln,
.die nicht mit den Säurehalogenidgruppen reagie ren, ein. Mol 4,Nitranilin in Form seines mineralsauren Salzes einwirken lässt.
Die so erhaltene, bisher nicht bekannte Verbindung soll als Zwischenprodukt für die Herstellung von Farbstoffen., pharmazeuti- schen Produkten und Textilhilfsmitbeln Ver wendung finden.
Beispiel: 1'30 Gewichtsteile Chlorterephthaloyl- c hloric <B>1</B> werden, in. 600 Volumteilen Aceton gelöst, und bei <B>50-601'</B> C werden.
87 Ge wichtsteile salzsaures 4-Nitranilin eingetra gen, worauf bis zur beginnenden Bildung von Chlorterephfihaloyl-di-(4-nitranilid) zum Sie den erhitzt wird. Hierauf wird sofort filtriert und durch starkes Abkühlen das Chlortereph- thaloyl-1-(4'-nitranilid)-4-ohlorid abgeschie den.
Das abgesaugte und mit kaltem Aceton gewaschene Produkt wird im Vakuum bei Zimmerbemperatur getrocknet. Durch Ein engen der Mutterlauge und anschliessendes Abkühlen werden weitere Mengen der Ver bindung erhalten.
An Stelle von Aceton als Lösungemitbel können andere Betone, wie Methyläthy lketon oder Diäthylketon, sowie Kohlen wasserstoffe, wie Benzol und Xylol, allein oder in Mi schung mit den bereits erwähnten Ketonen, ferner auch Dioxan verwendet werden..
Die erhaltene, bisher nicht bekannte Ver bindung bildet farblose Kristalle, die bei 94 bis 9'5 C schmelzen.
Process for the preparation of chloroterephthaloyl-1- (4'-nitranilide) -4-chloride. The subject of the present additional patent is a process for the production of chloroterephthaloyl-1- (4'-nitranilide) -4-chloride, which is characterized in that one mole of chloroterephthaloyl chloride in the presence of organic solvents,
.which do not react with the acid halide groups. Mol 4, nitroaniline in the form of its mineral acid salt.
The previously unknown compound obtained in this way is intended to be used as an intermediate for the production of dyes, pharmaceutical products and textile auxiliaries.
Example: 1'30 parts by weight of chloroterephthaloyl-chloric <B> 1 </B> are dissolved in 600 parts by volume of acetone and at <B> 50-601 '</B> C.
Enter 87 parts by weight of hydrochloric acid 4-nitroaniline, after which it is heated to you until chloroterephihaloyl-di- (4-nitranilide) begins to form. It is then filtered immediately and the chloroterephthaloyl-1- (4'-nitranilide) -4-chloride is deposited by vigorous cooling.
The product which has been filtered off with suction and washed with cold acetone is dried in vacuo at room temperature. By narrowing the mother liquor and then cooling it, further amounts of the compound are obtained.
Instead of acetone as a solution agent, other concretes such as methyl ethyl ketone or diethyl ketone, and hydrocarbons such as benzene and xylene, alone or in admixture with the ketones already mentioned, and also dioxane can be used.
The previously unknown compound obtained forms colorless crystals that melt at 94 to 9'5 ° C.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE205066X | 1936-12-23 | ||
| CH201953T | 1937-12-13 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH205066A true CH205066A (en) | 1939-05-31 |
Family
ID=25723757
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH205066D CH205066A (en) | 1936-12-23 | 1937-12-13 | Process for the preparation of chloroterephthaloyl-1- (4'-nitranilide) -4-chloride. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH205066A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2166739A1 (en) * | 1971-06-24 | 1975-10-09 | Suwa Seikosha Kk | Quartz-oscillator wrist watch - has frequency divider cct. and stepping motor |
| DE2131476C3 (en) | 1970-07-27 | 1976-03-04 | K.K. Suwa Seikosha, Tokio | Quartz crystal wrist watch |
-
1937
- 1937-12-13 CH CH205066D patent/CH205066A/en unknown
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2131476C3 (en) | 1970-07-27 | 1976-03-04 | K.K. Suwa Seikosha, Tokio | Quartz crystal wrist watch |
| DE2166739A1 (en) * | 1971-06-24 | 1975-10-09 | Suwa Seikosha Kk | Quartz-oscillator wrist watch - has frequency divider cct. and stepping motor |
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