CS266969B1 - Method of 3/2-ethylio-6-benzothiazolylaminomethyl/-2-benzothiazolinethione preparation - Google Patents
Method of 3/2-ethylio-6-benzothiazolylaminomethyl/-2-benzothiazolinethione preparation Download PDFInfo
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- CS266969B1 CS266969B1 CS877410A CS741087A CS266969B1 CS 266969 B1 CS266969 B1 CS 266969B1 CS 877410 A CS877410 A CS 877410A CS 741087 A CS741087 A CS 741087A CS 266969 B1 CS266969 B1 CS 266969B1
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- Czechoslovakia
- Prior art keywords
- benzothiazolinethione
- preparation
- benzothiazolylaminomethyl
- ethylthio
- ethylio
- Prior art date
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- 238000000034 method Methods 0.000 title claims abstract description 6
- 238000002360 preparation method Methods 0.000 title claims description 9
- TUMCWFMHZOUPDA-UHFFFAOYSA-N 2-ethylsulfanyl-1,3-benzothiazol-6-amine Chemical compound C1=C(N)C=C2SC(SCC)=NC2=C1 TUMCWFMHZOUPDA-UHFFFAOYSA-N 0.000 claims abstract description 6
- SDMPSCVFJMUEOS-UHFFFAOYSA-N 3-(hydroxymethyl)-1,3-benzothiazole-2-thione Chemical compound C1=CC=C2SC(=S)N(CO)C2=C1 SDMPSCVFJMUEOS-UHFFFAOYSA-N 0.000 claims abstract description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 10
- HIDZQGSTLAUXHW-UHFFFAOYSA-N 3-[[(2-ethylsulfanyl-1,3-benzothiazol-6-yl)amino]methyl]-1,3-benzothiazole-2-thione Chemical compound C12=CC=CC=C2SC(=S)N1CNC1=CC=C2N=C(SCC)SC2=C1 HIDZQGSTLAUXHW-UHFFFAOYSA-N 0.000 claims description 5
- 238000009835 boiling Methods 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 abstract description 3
- 229940121375 antifungal agent Drugs 0.000 abstract description 2
- 239000003429 antifungal agent Substances 0.000 abstract description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- YXIWHUQXZSMYRE-UHFFFAOYSA-N 1,3-benzothiazole-2-thiol Chemical compound C1=CC=C2SC(S)=NC2=C1 YXIWHUQXZSMYRE-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 238000006683 Mannich reaction Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
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- Agricultural Chemicals And Associated Chemicals (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Rieši sa spósob přípravy 3-(2-etyltio- -6-benzotiazolylamínometyl)-2-benzotiazolintiónu, pričom sa pósobí 3-hydroxymetyl-2- -benzotiazolíntiónomem na 2-etyltio-6-amínobenzotiazol. Zlúčenina sa používá ako účinná zložka antifungálnych prípravkov.The method of preparing 3- (2-ethylthio- 6-benzotiazolylamínometyl) -2-benzotiazolintiónu, with 3-hydroxymethyl-2- benzothiazolinothione to 2-ethylthio-6-aminobenzothiazole. The compound is used as effective component of antifungal agents.
Description
Predmetom vynálezu je spĎsob přípravy 3-(2-etyltio-6-benzotiazolylamínometyl)-2-benzotiazolíntiónu vzorcaThe present invention provides a process for the preparation of 3- (2-ethylthio-6-benzothiazolylaminomethyl) -2-benzothiazolinethione of the formula
Uvedená zlúčenina bola připravená Mannichovou syntézou z 2-etyltio-6-amínobenzotiazolu, formaldehydu a 2-benzotiazolíntiónu (iným názvom 2-merkaptobenzotiazolu) v zmesi metanolu a acetonu pri 40 až 45 °C (Holbová, E., Sidóová, E. a Odlerová, Ž., Chem. Zvěsti 30, 709 /1976/), alebo v etanole pri 45 až 50 °C (Holbová, E., Sidóová, E. a Zemanová, M.). Výťažok v obidvoch prípadoch bol 85 %-ný. Teraz bol zistený spĎsob přípravy uvedenej zlúčeniny, ktorý sa vyznačuje tým, že sa nechá reagovat 2-etyltio-6-amínobenzotiazol s 3-hydroxymetyl-2-benzotiazolíntiónom v acetone za varu.The title compound was prepared by Mannich synthesis from 2-ethylthio-6-aminobenzothiazole, formaldehyde and 2-benzothiazolinethione (also called 2-mercaptobenzothiazole) in a mixture of methanol and acetone at 40-45 ° C (Holbová, E., Sidóová, E. and Odlerová , Ž., Chem. Zvěsti 30, 709 (1976)), or in ethanol at 45-50 ° C (Holbová, E., Sidóová, E. and Zemanová, M.). The yield in both cases was 85%. A process for the preparation of said compound has now been found, which comprises reacting 2-ethylthio-6-aminobenzothiazole with 3-hydroxymethyl-2-benzothiazolinethione in boiling acetone.
Nasledujúce příklady bližšie osvetlujú ale nijako neobmedzujú přípravu 3-(2-etyltio-6-benzotiazolylamínometyl)-2-benzotiazolíntiónu z 2-etyltio-6-amínobenzotiazolu a 3-hydroxymetyl-2-benzotiazolíntiónu.The following examples illustrate but do not limit the preparation of 3- (2-ethylthio-6-benzothiazolylaminomethyl) -2-benzothiazolinethione from 2-ethylthio-6-aminobenzothiazole and 3-hydroxymethyl-2-benzothiazolinethione.
PříkladExample
Příprava 3-(2-etyltio-6-benzotiazolylamínometyl)-2-benzotiazolíntiónuPreparation of 3- (2-ethylthio-6-benzothiazolylaminomethyl) -2-benzothiazolinethione
2-etyltio-6-amínobenzotiazol (4,20 g, 0,020 mól), aceton (30 cm^) a 3-hydroxymetyl-2-benzotiazolíntión (3,94 g, 0,020 mól) sa spolu refluxovali 10 minút, potom sa zmes ochladila studenou vodou. Kraštalický produkt bielej farby sa premýval zmesou acetonu a etanolu v pomere 1:2 (15 cm^). Výťažok činil 7,70 g (99 %). Teplota topenia: 157 až 159 °C, čo sa zhoduje s hodnotou predtým uvedenou (Holbová, E., Sidóová, E. a Odlerová, Ž., Chem. Zvěsti 30, 709 /1976/).2-Ethylthio-6-aminobenzothiazole (4.20 g, 0.020 mol), acetone (30 cm 3) and 3-hydroxymethyl-2-benzothiazolinethione (3.94 g, 0.020 mol) were refluxed together for 10 minutes, then the mixture was cooled. cold water. The white crystalline product was washed with a 1: 2 (15 cm 3) mixture of acetone and ethanol. The yield was 7.70 g (99%). Melting point: 157-159 ° C, which corresponds to the value mentioned above (Holbová, E., Sidóová, E. and Odlerová, Ž., Chem. Zvěsti 30, 709 (1976)).
Pre c17H15N3S4 (389,59) vypočítané: 52,41 % C, 3,88 % H, 10,78 % N, 32,92 % S;For c 17 H 15 N 3 S 4 (389.59) calculated: 52.41% C, 3.88% H, 10.78% N, 32.92% S;
’ zistené: 52,64 % C, 3,94 » H, 10,81 % N, 32,76 % S.Found: 52.64% C, 3.94% H, 10.81% N, 32.76% S.
Významný je fakt, že spĎsob přípravy podlá vynálezu dává 99 %-ný výťažok v porovnaní s 85 %-ným výťažkom získaným predtým opísanými metodami.Significantly, the preparation method of the invention gives a 99% yield compared to the 85% yield obtained by the previously described methods.
3-(2-etyltio-6-benzotiazolylamínometyl)-2-benzotiazolíntión, připravený podlá příkladu, sa používá ako prostriedok s antifungálnym účinkom (Holbová, E., Sidóová, E. a Zemanová, Μ., cit. autorské osvedčenie).3- (2-ethylthio-6-benzothiazolylaminomethyl) -2-benzothiazolinethione, prepared according to the example, is used as an antifungal agent (Holbová, E., Sidóová, E. and Zemanová,,., Cited author's certificate).
SpĎsob přípravy podlá vynálezu možno aplikovat aj pre přípravu iných 3-(2-alkyltio-6-benzotiazolylamínometyl)-2-benzotiazolíntiónov.The preparation process according to the invention can also be applied to the preparation of other 3- (2-alkylthio-6-benzothiazolylaminomethyl) -2-benzothiazolinethiones.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS877410A CS266969B1 (en) | 1987-10-14 | 1987-10-14 | Method of 3/2-ethylio-6-benzothiazolylaminomethyl/-2-benzothiazolinethione preparation |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS877410A CS266969B1 (en) | 1987-10-14 | 1987-10-14 | Method of 3/2-ethylio-6-benzothiazolylaminomethyl/-2-benzothiazolinethione preparation |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CS741087A1 CS741087A1 (en) | 1989-05-12 |
| CS266969B1 true CS266969B1 (en) | 1990-01-12 |
Family
ID=5423169
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS877410A CS266969B1 (en) | 1987-10-14 | 1987-10-14 | Method of 3/2-ethylio-6-benzothiazolylaminomethyl/-2-benzothiazolinethione preparation |
Country Status (1)
| Country | Link |
|---|---|
| CS (1) | CS266969B1 (en) |
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1987
- 1987-10-14 CS CS877410A patent/CS266969B1/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CS741087A1 (en) | 1989-05-12 |
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