AT157724B - Process for the preparation of thiazoles unsubstituted at the 2-position. - Google Patents
Process for the preparation of thiazoles unsubstituted at the 2-position.Info
- Publication number
- AT157724B AT157724B AT157724DA AT157724B AT 157724 B AT157724 B AT 157724B AT 157724D A AT157724D A AT 157724DA AT 157724 B AT157724 B AT 157724B
- Authority
- AT
- Austria
- Prior art keywords
- thiazoles
- preparation
- unsubstituted
- weight
- parts
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title claims description 3
- 150000003557 thiazoles Chemical class 0.000 title claims description 3
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- OCVLSHAVSIYKLI-UHFFFAOYSA-N 3h-1,3-thiazole-2-thione Chemical class SC1=NC=CS1 OCVLSHAVSIYKLI-UHFFFAOYSA-N 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 239000003929 acidic solution Substances 0.000 claims 1
- 230000003647 oxidation Effects 0.000 claims 1
- 238000007254 oxidation reaction Methods 0.000 claims 1
- 125000003396 thiol group Chemical group [H]S* 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 2
- GQJDXGUXGNLKLO-UHFFFAOYSA-N 2-(4-methyl-2-sulfanylidene-3h-1,3-thiazol-5-yl)ethyl acetate Chemical compound CC(=O)OCCC=1SC(=S)NC=1C GQJDXGUXGNLKLO-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 1
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 1
- YNNGZCVDIREDDK-UHFFFAOYSA-N aminocarbamodithioic acid Chemical compound NNC(S)=S YNNGZCVDIREDDK-UHFFFAOYSA-N 0.000 description 1
- WDIHJSXYQDMJHN-UHFFFAOYSA-L barium chloride Chemical compound [Cl-].[Cl-].[Ba+2] WDIHJSXYQDMJHN-UHFFFAOYSA-L 0.000 description 1
- 229910001626 barium chloride Inorganic materials 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 229940075930 picrate Drugs 0.000 description 1
- OXNIZHLAWKMVMX-UHFFFAOYSA-M picrate anion Chemical compound [O-]C1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-M 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 150000007979 thiazole derivatives Chemical class 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Thiazole And Isothizaole Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
<Desc/Clms Page number 1>
Verfahren zur Darstellung von an der 2-Stellung nicht substituierten Thiazole.
EMI1.1
<Desc/Clms Page number 2>
[ss-chloräthyll-thiazol-chlorhydrat rein. Die Ausbeute beträgt 172 Gewichtsteile, das sind annähernd 87% der berechneten Menge.
Zur Reinigung des Thiazolderivates kann man sieh auch des schwerlöslichen Pikrates vom F = 1400 bedienen.
Beispiel 4 : 173 Gewichtsteile 2-Mercapto-4-methyl-5-[ss-acetoxyäthyl]-thiazol {aus 1-Acetoxy- 3-eblorpentanon- (4) und Ammoniumdithiocarbamat ; F = 93 } werden in 500 Gewichtsteilen Salzsäure (D = 1'18) gelöst und unter Rühren und intensiver Kühlung allmählich mit 272 Gewichtsteilen Wasserstoffsuperoxyd (30 Gew. % ig) versetzt. Man hält die Temperatur der Lösung auf 60-70 .
Nach beendigtem Zulauf des Oxydationsmittels erwärmt man auf 80 und versetzt mit einer heissen Lösung von 195 Gewichtsteilen kristallisiertem Bariumehlorid in 600 Gewichtsteilen Wasser.
Nach dem Abfiltrieren des Bariumsulfates engt man das Filtrat im Vakuum ein und verfährt zur Abtrennung und Reinigung des Produktes wie in Beispiel 1 beschrieben. Ausser dem Ersatz des Schwefels in 2-Stellung durch Wasserstoff wird bei der Umsetzung unter den vorstehend beschriebenen Bedingungen der Essigsäurerest durch Hydrolyse entfernt, so dass als Endprodukt 4-Methyl-5- [ss-oxyäthyl]-thiazol erhalten wird. An destillierter Base werden über 75% der theoretisch berechneten Menge gewonnen.
<Desc / Clms Page number 1>
Process for the preparation of thiazoles unsubstituted at the 2-position.
EMI1.1
<Desc / Clms Page number 2>
[ss-chloroethyll-thiazole-chlorohydrate pure. The yield is 172 parts by weight, which is approximately 87% of the calculated amount.
To purify the thiazole derivative, you can also use the sparingly soluble picrate of F = 1400
Example 4: 173 parts by weight of 2-mercapto-4-methyl-5- [β-acetoxyethyl] thiazole {from 1-acetoxy-3-eblorpentanone- (4) and ammonium dithiocarbamate; F = 93} are dissolved in 500 parts by weight of hydrochloric acid (D = 1'18), and 272 parts by weight of hydrogen peroxide (30% strength by weight) are gradually added with stirring and intensive cooling. The temperature of the solution is kept at 60-70.
When the addition of the oxidizing agent has ended, the mixture is heated to 80 and a hot solution of 195 parts by weight of crystallized barium chloride in 600 parts by weight of water is added.
After the barium sulfate has been filtered off, the filtrate is concentrated in vacuo and the procedure described in Example 1 is used to separate and purify the product. In addition to replacing the sulfur in the 2-position with hydrogen, the acetic acid residue is removed by hydrolysis during the reaction under the conditions described above, so that 4-methyl-5- [ss-oxyethyl] thiazole is obtained as the end product. More than 75% of the theoretically calculated amount is obtained from distilled base.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH157724X | 1937-03-12 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AT157724B true AT157724B (en) | 1940-01-10 |
Family
ID=4411800
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AT157724D AT157724B (en) | 1937-03-12 | 1938-02-02 | Process for the preparation of thiazoles unsubstituted at the 2-position. |
Country Status (1)
| Country | Link |
|---|---|
| AT (1) | AT157724B (en) |
-
1938
- 1938-02-02 AT AT157724D patent/AT157724B/en active
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