CS202336B1 - Method of preparing novel 6,11-dihydrodibenzo/b,e/thiepine-11-carboxylic acid - Google Patents
Method of preparing novel 6,11-dihydrodibenzo/b,e/thiepine-11-carboxylic acid Download PDFInfo
- Publication number
- CS202336B1 CS202336B1 CS651278A CS651278A CS202336B1 CS 202336 B1 CS202336 B1 CS 202336B1 CS 651278 A CS651278 A CS 651278A CS 651278 A CS651278 A CS 651278A CS 202336 B1 CS202336 B1 CS 202336B1
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- dihydrodibenzo
- thiepine
- carboxylic acid
- formula
- acid
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 4
- 238000009835 boiling Methods 0.000 claims description 2
- YQCZBDVYQPTZFJ-UHFFFAOYSA-N 6,11-dihydrobenzo[c][1]benzothiepine-11-carbonitrile Chemical compound C1SC2=CC=CC=C2C(C#N)C2=CC=CC=C21 YQCZBDVYQPTZFJ-UHFFFAOYSA-N 0.000 claims 1
- 150000002825 nitriles Chemical class 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 238000005903 acid hydrolysis reaction Methods 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 230000002526 effect on cardiovascular system Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material 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
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000000506 psychotropic effect Effects 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Tento vynález se týká způsobu přípravy nové kyseliny 6,ll-dihydrodibenzo(b, ejthiepin-ll-karboxylové vzorce I,The present invention relates to a process for the preparation of the novel 6,11-dihydrodibenzoic acid (b, ejthiepine-11-carboxylic acid of formula I,
Látka vzorce I je výhodným meziproduktem výroby farmakodynamicky účinných látek, zvláště léčiv ze skupin psychotropních, kardiovaskulárně aktivních a protizánětových látek.The compound of formula (I) is a preferred intermediate for the manufacture of pharmacodynamically active substances, in particular drugs of the psychotropic, cardiovascular and anti-inflammatory classes.
Způsob přípravy kyseliny vzorce I podle tohoto vynálezu spočívá v kyselé hydrolýze známého 6,ll-dihydrodibenzo(b, ejthiepin11-karbonitrilu (V. Seidlová a spol., Monatsh. Chem. 96, 650, 1965), vzorce IIThe process for the preparation of the acid of the formula I according to the invention consists in the acid hydrolysis of the known 6,11-dihydrodibenzo (b, ejthiepine-11-carbonitrile (V. Seidlová et al., Monatsh. Chem. 96, 650, 1965), formula II
K hydrolýze zvláště vhodná je vroucí zředěná ky slina sírová o koncentraci 40 až 60 %. Nová kyselina vzorce I je krystalická látka s t. t. 216,5 až 218 °C. Vykazuje charakteristické IČ a NMR spektrum, čehož lze použít k její identifikaci.Particularly suitable for hydrolysis is boiling dilute sulfuric acid having a concentration of 40 to 60%. The new acid of formula I is a crystalline substance having a melting point of 216.5 to 218 ° C. It shows a characteristic IR and NMR spectrum which can be used to identify it.
Další podrobnosti provedení přípravy látky I podle tohoto vynálezu jsou uvedeny v příkladu provedení, který je ovšem jen ilustrací možností vynálezu, aniž by bylo jeho účelem všechny tyto možnosti vyčerpávajícím způsobem popisovat.Further details of the preparation of the compound (I) according to the invention are given by way of example, which is only illustrative of the possibilities of the invention, but is not intended to fully describe all these possibilities.
PříkladExample
Směs 5,2 g 6,ll-dihydrodibenzo(b, ejthiepin-ll-karbonitrilu a 35 ml 55 % kyseliny sírové se vaří 5 hodin pod zpětným chladičem. Potom se zředí 100 ml vody, vodná fáze se oddělí dekantací od polopevného vyloučeného produktu, který se po promytí vodou rozpustí ve směsi 100 ml vody a 18 ml 20 % roztoku hydroxidu sodného. Vzniklý roztok sodné soli se zfiltruje s uhlím a filtrát se okyselí kyselinou solnou. Po stání do druhého dne se vyloučená kyselina 6,11-dihydrodibenzo (b, e) thiepin-ll-karboxylová vzorce I odsaje, promyje vodou a vysuší ve vakuu. Získá se 3,6 g (64 %) produktu s t. t.A mixture of 5.2 g of 6,11-dihydrodibenzo (b, ejthiepine-11-carbonitrile and 35 ml of 55% sulfuric acid) was refluxed for 5 hours, then diluted with 100 ml of water, The resulting sodium salt solution is filtered with charcoal and the filtrate is acidified with hydrochloric acid. After standing for the next day, the precipitated 6,11-dihydrodibenzoic acid (b. e) the thiepine-11-carboxylic acid of formula I is filtered off with suction, washed with water and dried in vacuo to give 3.6 g (64%) of the product with m.p.
211 až 213 °C. Krystalizaci z 90 % etanolu se získá čistá látka s t. t. 216,5 až 218 °C.Mp 211-213 ° C. Crystallization from 90% ethanol gave the pure material, m.p. 216.5-218 ° C.
202 336202 336
Claims (2)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS651278A CS202336B1 (en) | 1978-10-06 | 1978-10-06 | Method of preparing novel 6,11-dihydrodibenzo/b,e/thiepine-11-carboxylic acid |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS651278A CS202336B1 (en) | 1978-10-06 | 1978-10-06 | Method of preparing novel 6,11-dihydrodibenzo/b,e/thiepine-11-carboxylic acid |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS202336B1 true CS202336B1 (en) | 1980-12-31 |
Family
ID=5412322
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS651278A CS202336B1 (en) | 1978-10-06 | 1978-10-06 | Method of preparing novel 6,11-dihydrodibenzo/b,e/thiepine-11-carboxylic acid |
Country Status (1)
| Country | Link |
|---|---|
| CS (1) | CS202336B1 (en) |
-
1978
- 1978-10-06 CS CS651278A patent/CS202336B1/en unknown
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