AT314490B - Process for the preparation of new chloroformythioglycolic acid alkyl ester - Google Patents
Process for the preparation of new chloroformythioglycolic acid alkyl esterInfo
- Publication number
- AT314490B AT314490B AT393872A AT393872A AT314490B AT 314490 B AT314490 B AT 314490B AT 393872 A AT393872 A AT 393872A AT 393872 A AT393872 A AT 393872A AT 314490 B AT314490 B AT 314490B
- Authority
- AT
- Austria
- Prior art keywords
- preparation
- new
- acid alkyl
- chloroformythioglycolic
- alkyl ester
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 4
- 239000002253 acid Substances 0.000 title description 2
- 125000005907 alkyl ester group Chemical group 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- SKQZZBCDZBGESR-UHFFFAOYSA-N COC(C(C(Cl)=O)S)=O Chemical compound COC(C(C(Cl)=O)S)=O SKQZZBCDZBGESR-UHFFFAOYSA-N 0.000 description 1
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- WOAZEKPXTXCPFZ-UHFFFAOYSA-N dimethyl(phenyl)azanium;chloride Chemical compound Cl.CN(C)C1=CC=CC=C1 WOAZEKPXTXCPFZ-UHFFFAOYSA-N 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C329/00—Thiocarbonic acids; Halides, esters or anhydrides thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
<Desc/Clms Page number 1>
Die Erfindung betrifft ein Verfahren zur Herstellung neuer Chlorformylthioglykolsäurealkylester der allgemeinen Formel
EMI1.1
worin Rl Wasserstoff oder Alkyl mit 1 bis 4 Kohlenstoffatomen bedeutet und R für Alkyl mit 1 bis 4 Kohlenstoffatomen steht.
Das erfindungsgemässe Verfahren ist dadurch gekennzeichnet, dass man Verbindungen der allgemeinen.
Formel
EMI1.2
worin Rl und R, obige Bedeutung haben, mit Phosgen umsetzt.
Die Umsetzung erfolgt zweckmässigerweise in einem organischen Lösungsmittel, wie Benzol oder Toluol, und in Gegenwart eines Säurebindemittels, wie Dimethylanilin oder Pyridin, unter wasserfreien Bedingungen
EMI1.3
Die Verbindungen der Formel (I) stellen interessante Zwischenprodukte dar und können beispielsweise zur Herstellung von Sulfonamiden verwendet werden.
Beispiel : Chlorformylthioglykolsäuremethylester.
EMI1.4
kühlen über einen Zeitraum von etwa 2 h in eine Lösung von 188 g Phosgen in 850 ml absolutem Benzol eingetragen. Nach Stehen über Nacht wird vom ausgefallenen Dimethylanilin-Hydrochlorid abgesaugt und mit Benzol nachgewaschen. Nach Extraktion der Benzol-Lösung mit Wasser wird im Vakuum eingeengt und der Rückstand fraktioniert destilliert. Man erhält eine farblose Flüssigkeit vom Sdp. 92 bis 930C/13 mm.
**WARNUNG** Ende DESC Feld kannt Anfang CLMS uberlappen**.
<Desc / Clms Page number 1>
The invention relates to a process for the preparation of new chloroformylthioglycolic acid alkyl esters of the general formula
EMI1.1
where Rl is hydrogen or alkyl having 1 to 4 carbon atoms and R is alkyl having 1 to 4 carbon atoms.
The inventive method is characterized in that compounds of the general.
formula
EMI1.2
where Rl and R, have the above meaning, reacts with phosgene.
The reaction is conveniently carried out in an organic solvent, such as benzene or toluene, and in the presence of an acid binding agent, such as dimethylaniline or pyridine, under anhydrous conditions
EMI1.3
The compounds of the formula (I) are interesting intermediates and can be used, for example, for the preparation of sulfonamides.
Example: chloroformylthioglycolic acid methyl ester.
EMI1.4
cool added over a period of about 2 h in a solution of 188 g of phosgene in 850 ml of absolute benzene. After standing overnight, the precipitated dimethylaniline hydrochloride is filtered off with suction and washed with benzene. After the benzene solution has been extracted with water, it is concentrated in vacuo and the residue is fractionally distilled. A colorless liquid with a bp 92 to 930 ° C./13 mm is obtained.
** WARNING ** End of DESC field may overlap beginning of CLMS **.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AT393872A AT314490B (en) | 1970-04-03 | 1970-04-03 | Process for the preparation of new chloroformythioglycolic acid alkyl ester |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AT393872A AT314490B (en) | 1970-04-03 | 1970-04-03 | Process for the preparation of new chloroformythioglycolic acid alkyl ester |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AT314490B true AT314490B (en) | 1974-04-10 |
Family
ID=3557460
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AT393872A AT314490B (en) | 1970-04-03 | 1970-04-03 | Process for the preparation of new chloroformythioglycolic acid alkyl ester |
Country Status (1)
| Country | Link |
|---|---|
| AT (1) | AT314490B (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2462423A1 (en) * | 1979-07-25 | 1981-02-13 | Ppg Industries Inc | PROCESS FOR OBTAINING CHLOROTHIOLFORMIATES |
-
1970
- 1970-04-03 AT AT393872A patent/AT314490B/en not_active IP Right Cessation
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2462423A1 (en) * | 1979-07-25 | 1981-02-13 | Ppg Industries Inc | PROCESS FOR OBTAINING CHLOROTHIOLFORMIATES |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| ELJ | Ceased due to non-payment of the annual fee |