CH282937A - Process for the preparation of an acylating agent. - Google Patents
Process for the preparation of an acylating agent.Info
- Publication number
- CH282937A CH282937A CH282937DA CH282937A CH 282937 A CH282937 A CH 282937A CH 282937D A CH282937D A CH 282937DA CH 282937 A CH282937 A CH 282937A
- Authority
- CH
- Switzerland
- Prior art keywords
- acylating agent
- pyridine
- preparation
- thiophene
- carboxylic acid
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 14
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 7
- QERYCTSHXKAMIS-UHFFFAOYSA-N thiophene-2-carboxylic acid Chemical compound OC(=O)C1=CC=CS1 QERYCTSHXKAMIS-UHFFFAOYSA-N 0.000 claims description 6
- 239000003795 chemical substances by application Substances 0.000 claims description 5
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims description 4
- 230000010933 acylation Effects 0.000 claims description 2
- 238000005917 acylation reaction Methods 0.000 claims description 2
- 239000000987 azo dye Substances 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims description 2
- BGMIRDHBNWQSGE-UHFFFAOYSA-N hypochlorous acid;pyridine Chemical compound ClO.C1=CC=NC=C1 BGMIRDHBNWQSGE-UHFFFAOYSA-N 0.000 claims 1
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D333/38—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
Description
Verfahren zur Herstellung eines Acylierungamittels. Es wurde gefunden, dass man ein wertvol les Acylierungsmittel erhält, wenn man Thio- phen-2-earbonsäure-5-sulfonsäure in Gegen wart eines Übersehusses an Pyridin mit Phos- gen behandelt..
Das erhaltene neue Acylierungsmittel ist eine dunkelbraune, nicht gelöstes Pyridin- ehlorhydrat enthaltende Lösung, die sich zur Acylierung der verschiedensten -NH-C7rup- pen und -ON-Gruppen enthaltenden Verbin dungen, z. B. von Azofarbstoffen, eignet und die Einführung von Resten der Formel
EMI0001.0016
in solchen Verbindungen ermöglicht.
Die als Ausgangsstoff verwendbare Thio- phen-2-carbonsäure-5-sulfonsäure kann zum Beispiel durch Umsetzung von Thiophen-2-car- bonsäure mit Sehwefeltrioxyd in flüssigem Schwefeldioxyd hergestellt werden.
Pyridin muss beim vorliegenden Verfahren im Überschuss vorhanden sein, d. h. es muss mehr Pyridin vorhanden sein, als zur Absät- tigung sämtlicher im Reaktionsgemiseh an wesender Säuregruppen erforderlich ist.
Zweckmässig wird die Thiophen-2-carbon- säure-5-stilfonsäure in Pyridin eingetragen und hierauf bei einer etwas erhöhten Tem peratur, z. B. bei 30 bis 40 , gasförmiges Phos- gen allmählich eingeleitet.
<I>Beispiel:</I> 1.0,4 Teile Thiophen-2-carbonsäure-5-sulfon- säure werden in 60 Volumteilen trockenem Pyridin unter Rühren gelöst und 6 Teile Phos- gen bei 30 bis 40 innert 1 bis 11/2 Stunden in der erhaltenen Lösung eingeleitet.
Process for the preparation of an acylating agent. It has been found that a valuable acylating agent is obtained if thiophene-2-carboxylic acid-5-sulfonic acid is treated with phosgene in the presence of an excess of pyridine.
The new acylating agent obtained is a dark brown, undissolved pyridine ehlorhydrat containing solution, which is used for acylation of various -NH-C7rup- and -ON groups containing compounds, eg. B. of azo dyes, and the introduction of residues of the formula
EMI0001.0016
enabled in such connections.
The thiophene-2-carboxylic acid-5-sulfonic acid which can be used as a starting material can be produced, for example, by reacting thiophene-2-carboxylic acid with sulfur trioxide in liquid sulfur dioxide.
In the present method, pyridine must be present in excess, i.e. H. more pyridine must be present than is necessary to saturate all of the acid groups present in the reaction mixture.
The thiophene-2-carboxylic acid-5-stilfonic acid is expediently registered in pyridine and then at a slightly elevated temperature, e.g. B. at 30 to 40, gaseous phosgene gradually introduced.
<I> Example: </I> 1.0.4 parts of thiophene-2-carboxylic acid-5-sulfonic acid are dissolved in 60 parts by volume of dry pyridine with stirring and 6 parts of phosgene at 30 to 40 within 1 to 11/2 hours initiated in the resulting solution.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH282937T | 1949-07-22 | ||
| CH276416T | 1949-07-22 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH282937A true CH282937A (en) | 1952-05-15 |
Family
ID=25731694
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH282937D CH282937A (en) | 1949-07-22 | 1949-07-22 | Process for the preparation of an acylating agent. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH282937A (en) |
-
1949
- 1949-07-22 CH CH282937D patent/CH282937A/en unknown
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