CH137949A - Process for the preparation of a halogenated arylthioglycolic acid. - Google Patents
Process for the preparation of a halogenated arylthioglycolic acid.Info
- Publication number
- CH137949A CH137949A CH137949DA CH137949A CH 137949 A CH137949 A CH 137949A CH 137949D A CH137949D A CH 137949DA CH 137949 A CH137949 A CH 137949A
- Authority
- CH
- Switzerland
- Prior art keywords
- acid
- preparation
- trichlorobenzene
- halogenated
- arylthioglycolic
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 title claims description 6
- 238000000034 method Methods 0.000 title claims description 4
- 239000002253 acid Substances 0.000 title claims description 3
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 claims description 3
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 claims description 3
- 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 2
- 239000000975 dye Substances 0.000 claims description 2
- 239000000155 melt Substances 0.000 claims description 2
- -1 1,2.3-trichlorobenzene-5-thioglycolic acid Chemical compound 0.000 description 3
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Darstellung einer halogenierten Arylthioglylzolsäure. Vorliegendes Patent bezieht sich auf ein Verfahren zur Darstellung der 1.2.3-Tri- chlorbenzol-5-thioglykolsäure der Formel
EMI0001.0005
dadurch gekennzeichnet, dass man 1.2.3- Trichlorbenzol - 5 - sulfosäure Chlorsulfonsäure bei Temperaturen unter 100 einwirken lässt,
das so erhaltene 1.2.3-Trichlorbenzol-5- sulfochlorid zum Merkaptan reduziert und letzteres mit Monochloressigsäure konden siert.
Die so erhaltene 1.2.3-Trichlorbenzol-5- thioglykolsäure schmilzt in reinem Zustand bei 136 und soll als Zwischenprodukt zur Darstellung von Farbstoffen Verwendung finden. <I>Beispiel:</I> 145 kg 1.2.3-trichlorbenzol-5-sulfosau- res Natrium, hergestellt zum Beispiel aus der 2.6-Diamino-l-chlorbenzol-4-sulfosäure durch Ersatz der Aminogruppen durch Chlor nach Sandmeyer, werden bei gewöhnlicher Temperatur in 400 kg Chlorsulfonsäure un ter Rühren eingetragen, hierauf das Gemisch etwa 1 Stunde bei etwa<B>50'</B> gehalten, ab gekühlt und auf Eiswasser gegossen.
Das so erhaltene 1.2.3-Trichlorbenzol-5-sulfochlorid wird wie das Sulfochlorid im Beispiel des Haupt patentes zum Merkaptan reduziert und letz teres durch Kondensation mit Monochloressig- säure in die 1.2.3-Trichlorbenzol-5-thioglykol- säure vom Schmelzpunkt 136 übergeführt.
Process for the preparation of a halogenated arylthioglylzolic acid. The present patent relates to a process for the preparation of 1,2.3-trichlorobenzene-5-thioglycolic acid of the formula
EMI0001.0005
characterized in that 1.2.3- trichlorobenzene - 5 - sulfonic acid chlorosulfonic acid is allowed to act at temperatures below 100,
the 1,2.3-trichlorobenzene-5-sulfochloride thus obtained is reduced to the mercaptan and the latter is condensed with monochloroacetic acid.
The 1,2,3-trichlorobenzene-5-thioglycolic acid obtained in this way melts in the pure state at 136 and is said to be used as an intermediate for the preparation of dyes. <I> Example: </I> 145 kg of 1.2.3-trichlorobenzene-5-sulfonic acid sodium, produced for example from 2.6-diamino-1-chlorobenzene-4-sulfonic acid by replacing the amino groups with chlorine according to Sandmeyer added at normal temperature to 400 kg of chlorosulfonic acid with stirring, then the mixture was kept at about 50 for about 1 hour, cooled and poured onto ice water.
The 1,2,3-trichlorobenzene-5-sulfochloride obtained in this way is reduced to the mercaptan like the sulfochloride in the example of the main patent, and the latter is converted into 1,2,3-trichlorobenzene-5-thioglycolic acid with a melting point of 136 by condensation with monochloroacetic acid .
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE137949X | 1927-03-24 | ||
| CH135217T | 1928-03-17 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH137949A true CH137949A (en) | 1930-01-31 |
Family
ID=25712462
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH137949D CH137949A (en) | 1927-03-24 | 1928-03-17 | Process for the preparation of a halogenated arylthioglycolic acid. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH137949A (en) |
-
1928
- 1928-03-17 CH CH137949D patent/CH137949A/en unknown
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