CH201957A - Process for the preparation of 2-methylhexahydrobenzthiazole. - Google Patents
Process for the preparation of 2-methylhexahydrobenzthiazole.Info
- Publication number
- CH201957A CH201957A CH201957DA CH201957A CH 201957 A CH201957 A CH 201957A CH 201957D A CH201957D A CH 201957DA CH 201957 A CH201957 A CH 201957A
- Authority
- CH
- Switzerland
- Prior art keywords
- methylhexahydrobenzthiazole
- preparation
- reacted
- reaction
- base
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 7
- KMTWSJDKGKRNIP-UHFFFAOYSA-N 2-methyl-2,3,3a,4,5,6-hexahydro-1,3-benzothiazole Chemical compound CC1SC=2C(N1)CCCC2 KMTWSJDKGKRNIP-UHFFFAOYSA-N 0.000 title description 3
- 238000002360 preparation method Methods 0.000 title description 3
- 238000006243 chemical reaction Methods 0.000 claims description 5
- 238000009833 condensation Methods 0.000 claims description 2
- 230000005494 condensation Effects 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- YUKQRDCYNOVPGJ-UHFFFAOYSA-N thioacetamide Chemical compound CC(N)=S YUKQRDCYNOVPGJ-UHFFFAOYSA-N 0.000 claims description 2
- DLFVBJFMPXGRIB-UHFFFAOYSA-N thioacetamide Natural products CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 2
- ANRHNWWPFJCPAZ-UHFFFAOYSA-M thionine Chemical compound [Cl-].C1=CC(N)=CC2=[S+]C3=CC(N)=CC=C3N=C21 ANRHNWWPFJCPAZ-UHFFFAOYSA-M 0.000 claims description 2
- BMHZEQGOBNCVHX-UHFFFAOYSA-N 2,3,3a,4,5,6-hexahydro-1,3-benzothiazole Chemical compound C1CCC=C2SCNC21 BMHZEQGOBNCVHX-UHFFFAOYSA-N 0.000 claims 1
- 238000009835 boiling Methods 0.000 claims 1
- 238000010438 heat treatment Methods 0.000 claims 1
- 239000000049 pigment Substances 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000000975 dye Substances 0.000 description 2
- RTZWBJIYBWNJMR-UHFFFAOYSA-N 2-chlorocyclohexan-1-amine Chemical compound NC1CCCCC1Cl RTZWBJIYBWNJMR-UHFFFAOYSA-N 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- -1 halo alkene Chemical class 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 125000001475 halogen functional group Chemical group 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Landscapes
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Description
Verfahren zur Herstellung von 2-Methylhexahydrobenzthiazol. Es wurde gefunden, dass man das bisher noch nicht bekannte 2: Mothylhexahyd.robenz- thiazol erhalten kann, wenn man .ein o-Halo- gency elohexylamin mit Thioaoetamid zur Reaktion bringt. Man. erhält auf ,diese Weise ,
die Verbindung von der Formel
EMI0001.0017
Das o-Halomencyclohiexylamin kann nach Osterburg ct Kendall (Journ. of the Am. Chein. Soe., Bd. 42, 1920, S.2621--25) er halten werden. Die Reaktionskomponenten können als solche allein oder unter Anwen- danvon Verdünnungsmitteln zur Reaktion Y;ebracht werden. Zweckmässig wird bei der Reaktion erwärmt.
Das nach dem Verfahren hergestellte 2- Met.h\ lhexahydrobenzthiazol ist ein wert- volles Ausgangsprodukt zur Herstellung von Sensibilisatoren für photographische Ha logensilberemulsionen. indem quartäre Am moniumsalze dieser Base nach an sich be kannten Verfahren miteinander oder mit an dern heterocyclischen Basen zu Cyaninfarb- stoffen kondensiert werden. <I>Beispiel:</I> 26,5 g o-Chlorcyclohexylamin werden mit 7 5 g Thioacetamid innig vermischt. Nach kurzem Erwärmen findet eine kräftige Re aktion statt.
Zur Vervollständigung der selben erhitzt man noch gegen 15 Minuten <B>auf</B> dem Dampfbad, versetzt dann den An satz zur Aufarbeitung unter Kühlung mit 100 cm'@ 20 proz. Natronlauge und nimmt die gebildete Base mit Äther auf. Die ätherische Lösung wird getrocknet, und der nach Ab destillieren des Äthers hinterbleibende Rück stand wird bei vermindertem Druck fraktio niert. Bei 10 mm geht das 2-Methylhega- hydrobenzthiazol zwischen 130 bis IM' als gelbliches<B>01</B> über.
Die Base kann leicht. mit Halobenalkvlen zu den entsprechenden diiar- tären Halobenalkvlaten umgesetzt -erden. die zur Weiterkondensation zur Herstellung der Cyanfarbstoffe dienen.
Process for the preparation of 2-methylhexahydrobenzthiazole. It has been found that the hitherto unknown 2: methylhexahyd.robenzthiazole can be obtained if an o-halogenocylohexylamine is reacted with thioaoetamide. Man. get on, this way,
the compound of the formula
EMI0001.0017
The o-halomencyclohiexylamine can be obtained from Osterburg ct Kendall (Journ. Of the Am. Chein. Soe., Vol. 42, 1920, pp. 2621-25). The reaction components can be brought to reaction Y as such alone or with the use of diluents. The reaction is expediently heated.
The 2-methylhexahydrobenzthiazole produced by this process is a valuable starting product for the production of sensitizers for photographic halogen silver emulsions. by condensing quaternary ammonium salts of this base by processes known per se with one another or with other heterocyclic bases to form cyanine dyes. <I> Example: </I> 26.5 g of o-chlorocyclohexylamine are intimately mixed with 75 g of thioacetamide. A strong reaction takes place after a short period of warming.
To complete the same process, the mixture is heated for another 15 minutes on the steam bath, then added to the preparation for work-up while cooling with 100 cm @ 20 percent. Sodium hydroxide solution and absorbs the base formed with ether. The ethereal solution is dried, and the residue that remains after the ether has been distilled off is fractionated under reduced pressure. At 10 mm, the 2-methyl hegahydrobenzthiazole changes to a yellowish <B> 01 </B> between 130 and 1 M '.
The base can easily. implemented with halo alkales to form the corresponding diarytary halo alkene. which are used for further condensation to produce the cyan dyes.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE201957X | 1936-09-16 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH201957A true CH201957A (en) | 1938-12-31 |
Family
ID=5768915
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH201957D CH201957A (en) | 1936-09-16 | 1937-09-10 | Process for the preparation of 2-methylhexahydrobenzthiazole. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH201957A (en) |
-
1937
- 1937-09-10 CH CH201957D patent/CH201957A/en unknown
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