CS231606B1 - Process for preparing 6-benzoylamino-2-benzothiazolinethione - Google Patents
Process for preparing 6-benzoylamino-2-benzothiazolinethione Download PDFInfo
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- CS231606B1 CS231606B1 CS812959A CS295981A CS231606B1 CS 231606 B1 CS231606 B1 CS 231606B1 CS 812959 A CS812959 A CS 812959A CS 295981 A CS295981 A CS 295981A CS 231606 B1 CS231606 B1 CS 231606B1
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Abstract
Vynálezom je sposob přípravy 6-benzo- ylamino-2-benzotiazolínti6nu. učelom vynálezu je energeticky a časové menej náročná příprava 6-benzoylamino- -2-benzotiázolíntiónu vzorca Reakcia sa uskutečňuje acyláciou 6-amino- -2benzotiazolínti6nu benzoychloriáon za použitia 5 až 7 ekvivalentov suchého py ridinu ako rozpúšíadla. 6-benzoylamino-2 “ benzotiazolíntion je medziprodukton pre syntézu antimyobak- teriálne účinných 2-alkyltio-6-benzoyla- mino-benzotiazolov.The invention is a method for the preparation of 6-benzoylamino-2-benzothiazoline thiene. The purpose of the invention is the less energy- and time-consuming preparation of 6-benzoylamino-2-benzothiazolinthione of the formula The reaction is carried out by acylation of 6-amino-2-benzothiazolinthione with benzoyl chloride using 5 to 7 equivalents of dry pyridine as a solvent. 6-benzoylamino-2" benzothiazolinthione is an intermediate for the synthesis of antimyobacterially active 2-alkylthio-6-benzoylamino-benzothiazoles.
Description
1 231 BOfl
Predmetom vynálezu je spBsob přípravy 6-benzoylamino-2-— benzotiazolíntiénv vzorea
Uvedená zlúčenina bola připravená /Kuznecova, E. A·, 2u-ravlev, S. V. a Stepanova, T. N., Chim. Geterocikl. Sojed., 1967»261·/ tým sposobom, že k zmesi 6-amino-2-benzotiazolíntiónu /0,1mol/ a pyridinu /12 ml, 0,15 mol/ v dioxáne /400 ml/ bol přidanýbenzoylchlorid /12 ml/ v dioxáne /200 ml/ a reakčná zmes sa refluxovala 4 hodiny· Výtažok produktu s t.t. 247 až 248 °C bol 72 %.
Teraz bol zistený sposob přípravy uvedenej zlúčeniny, ktorýje úspornější z hladiska spotřeby energie a reakČnej doby a vyznáčujesa tým, že aeyláeia sa uskutočftuje v přítomnosti nadbytečné-ho množstva pyridinu /5 aí 7 ekvivaientov/, slúžiaceho ako rozpú-štadlo. Příklad 1 Příprava 6-bensoylanino-2-benzotiazolíntiénu K směsi 6-amino-2-benzotiazolíntiénu /18,2 g, 0,1 mol/ abenzeylchloridu/16,8 g, 0,12 mel/ sa přidal suchý pyridin /50 ml, 2 231 βΟβ 49 g> Ο»^2 mol/, přičο nastala exoterané reakcia. Zmes sa od-stavila na 10 ainút a potom 15 minút sa zahrievala na vodném kú-peli, pričom úplné stuhla. K snesl sa přidala studená voda /500ml/, potom sa okyslila koncentrovanou kyselinou chlorovodíkovouna pH 5 na univerzálny indikátor. Tuhý podiel bol odsátý a pro-kryžtalizovaný zo znesi aceton - etanol - voda v pomere 5:2:1za použitia aktivněho uhlia. Získal sa 6-benzoylamino-2-benzo-tiazolíntión s t.t. 247 249 °C v množštve 20,8 g /72,7 %/.
Literatúra /Kuznecova, E. A., Žuravlev, S. V. a Stepanova, T. N.tChin. Geterocikl. Sojed., 1967» 261./ udává t..t· 247 až 248 *Ca výtažok 72 %· M.h.: 286,58
Pro CUH1ON2OS2 vypočítané': 0 58,72 H 3,52 N 9,78 S 22,59zistoné % : 59,02 3,52 9,75 22,50 6-Benzoylamino-2-benzotiazolíntión, připravený podlá příkla-du 1 sa používá ako medziprodukt pri syntéze antimykebakteriálnevysoko účinnéj zlúčeniny vzorca
ktoré sa získává alkyláciou draselnéj soli 6-benzoylamino-2-mer-kaptobenáotiazolu, vznikájúcej rozpuštěním zlúčeniny podlá vyná-lezu v roztoku hydroxidu draselného /Sidóová, E. a Odlerová, Z.,Csl. AO 207299 /1980/./, ako aj pri syntéze flalžích antimykobak- teriálne účinných 2-alkyltio-6-benzoylaminobénzbtiazolov /Sidó- v ová, E. a Odlerová, 2, 2.Í5 OJb.
1,231 BOfl
The present invention provides a process for the preparation of 6-benzoylamino-2-benzothiazolinethione
Said compound was prepared (Kuznetsova, E.A., 2u-ravlev, SV and Stepanova, TN, Chim.). Geterocikl. Benzoyl chloride (12 ml) was added to a mixture of 6-amino-2-benzothiazolinothione (0.1 mol) and pyridine (12 ml, 0.15 mol) in dioxane (400 ml). dioxane (200 mL) and the reaction mixture was refluxed for 4 hours. The yield of the product, mp 247-248 ° C, was 72%.
A method for preparing said compound has now been found which is more economical in terms of energy consumption and reaction time and is characterized by the fact that aeylaeium is carried out in the presence of an excess amount of pyridine (5 to 7 equivalents) serving as solvent. EXAMPLE 1 Preparation of 6-Bensoylanino-2-benzothiazolinethene Dry pyridine / 50 ml was added to a mixture of 6-amino-2-benzothiazolinothione / 18.2 g, 0.1 mol / abenzyl chloride (16.8 g, 0.12 m) 2 231 βΟβ 49 g> ^ ^ 2 mol /, resulting in exothermic reaction. The mixture was allowed to stand for 10 minutes and then heated on a water bath for 15 minutes while solidifying. Cold water (500ml) was added, then acidified with concentrated hydrochloric acid pH 5 to a universal indicator. The solid was sucked off and crystallized from acetone-ethanol-water 5: 2: 1 to use activated charcoal. There was obtained 6-benzoylamino-2-benzothiazolinothione with mp 247 249 ° C at 20.8 g (72.7%).
Literature / Kuznecova, EA, Zuravlev, SV and Stepanova, TNtChin. Geterocikl. Sojed., 1967 »261./ gives t..t · 247-248 * Ca 72% yield · Mh: 286,58
For CUH1ON2OS2 calculated ': 0 58.72 H 3.52 N 9.78 S 22.59one%: 59.02 3.52 9.75 22.50 6-Benzoylamino-2-benzothiazolinothione, prepared according to Example 1, is used as an intermediate in the synthesis of an antimycebacterial compound of the formula
which is obtained by the alkylation of the potassium salt of 6-benzoylamino-2-mercaptobenothiazole resulting from the dissolution of the compound according to the invention in potassium hydroxide solution / Sidóová, E. and Odlerová, Z., Csl. AO 207299 /1980/./, as well as in the synthesis of antimycobacterial-active 2-alkylthio-6-benzoylaminobenzothiazoles / Sidon, E. and Odler, 2, 25 OJb.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS812959A CS231606B1 (en) | 1981-04-21 | 1981-04-21 | Process for preparing 6-benzoylamino-2-benzothiazolinethione |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS812959A CS231606B1 (en) | 1981-04-21 | 1981-04-21 | Process for preparing 6-benzoylamino-2-benzothiazolinethione |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CS295981A1 CS295981A1 (en) | 1984-04-16 |
| CS231606B1 true CS231606B1 (en) | 1984-12-14 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS812959A CS231606B1 (en) | 1981-04-21 | 1981-04-21 | Process for preparing 6-benzoylamino-2-benzothiazolinethione |
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| Country | Link |
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| CS (1) | CS231606B1 (en) |
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1981
- 1981-04-21 CS CS812959A patent/CS231606B1/en unknown
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| CS295981A1 (en) | 1984-04-16 |
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