PL434B1 - The method of obtaining bromoacylated urea derivatives. - Google Patents
The method of obtaining bromoacylated urea derivatives. Download PDFInfo
- Publication number
- PL434B1 PL434B1 PL434A PL43420A PL434B1 PL 434 B1 PL434 B1 PL 434B1 PL 434 A PL434 A PL 434A PL 43420 A PL43420 A PL 43420A PL 434 B1 PL434 B1 PL 434B1
- Authority
- PL
- Poland
- Prior art keywords
- obtaining
- urea derivatives
- bromoacylated
- parts
- urea
- Prior art date
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- 150000003672 ureas Chemical class 0.000 title claims description 3
- 239000003054 catalyst Substances 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- OPNPQXLQERQBBV-UHFFFAOYSA-N carbromal Chemical compound CCC(Br)(CC)C(=O)NC(N)=O OPNPQXLQERQBBV-UHFFFAOYSA-N 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 235000019658 bitter taste Nutrition 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- NOGFHTGYPKWWRX-UHFFFAOYSA-N 2,2,6,6-tetramethyloxan-4-one Chemical compound CC1(C)CC(=O)CC(C)(C)O1 NOGFHTGYPKWWRX-UHFFFAOYSA-N 0.000 description 1
- -1 Propionyl-bromo-diethyl-acetyl-urea forms Chemical group 0.000 description 1
- 230000003444 anaesthetic effect Effects 0.000 description 1
- 235000013877 carbamide Nutrition 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 235000019439 ethyl acetate Nutrition 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000009965 odorless effect Effects 0.000 description 1
- 230000002085 persistent effect Effects 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000001624 sedative effect Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
Description
Stwierdzono, ze przy traktowaniu bro¬ moacylowanych moczników srodkami a- cylujacemi, w obecnosci katalizatorów, o- trzymuje sie produkty, które odznaczaja sie nadzwyczaj szybko nastepujacem, lecz jednoczesnie trwalem dzialaniem usypia- jacem i sedatywnem.Przyklad 1. 474 cz. wag. bromo-dwuetylo-acetylo- mocznika ogrzewa sie w ciagu 1 godz. na lazni wodnej do 60° z 1000 cz. wagowych bezwodnika octowego i 75 cz. wag. chlor¬ ku cynku. Produkt reakcji ochladza sie i wlewa go wtedy, mieszajac, do 3000 cz. wagów, wody z lodem. Po dluzszem staniu odciaga sie mase krystaliczna i przekry- stalizowuje z rozcienczonego goracego al¬ koholu. Otrzymuje sie acetylowany bro- mo-dwuetylo-acetylo-mocznik z wysmieni¬ ta wydajnoscia.Preparat ten tworzy bezbarwne i pozba¬ wione zapachu krysztaly o slabo gorzkim smaku. Rozpuszcza sie latwo w alkohoia, eterze, acetonie, chloroformie i estrze octo¬ wym, troche trudno w wodzie. Punkt topli¬ wosci 108 — 109°.Przyklad 2.Ogrzewa sie lekko 237 cz. bromo-dwu- etylo-acetylo-mocznika i 130 cz. wag. bez¬ wodnika propjonowego z '20 cz. kwasu siarkowego, w ciagu 40 minut. Po ozie¬ bieniu miesza sie z 1000 cz. wag. wody lodowej i odciaga wydzielona mase kry¬ staliczna. Oczyszcza sie przekrystalizo- waniem z benzolu lub rozcienczonego alko¬ holu.Propjonylo - bromo-dwuetylo-acetylo- mocznik tworzy bezbarwne krysztaly o smaku gorzkim. Sa one latwo rozpuszczal-ne w alkoholu i benzolu, malo rozpuszczal¬ ne w wodzie. Punkt topliwosci 103°. Miast bezwodnika propjonowego moze byc uzy¬ ty bezwodnik benzoesowy. Otrzymany w ten sposób produkt topi sie przy 139 — 140°. PLIt has been found that by treating bromacylated ureas with acylating agents in the presence of catalysts, products are obtained which are distinguished by extremely fast, but at the same time persistent, anesthetic and sedative effects. Example 1. 474 part. wt. The bromo-diethyl-acetyl-urea is heated for 1 hour. in a water bath up to 60 ° with 1000 parts by weight of acetic anhydride and 75 parts. wt. zinc chloride. The reaction product is cooled and then poured into 3000 parts with stirring. scales, ice water. After prolonged standing, the crystalline mass is removed and crystallized from the diluted hot alcohol. Acetylated bromo-diethyl-acetyl-urea is obtained in exquisite yield. This formulation forms colorless and odorless crystals with a slightly bitter taste. It dissolves easily in alcohol, ether, acetone, chloroform and acetic ester, slightly difficult in water. Melting point 108-109 °. Example 2 Heats slightly 237 parts. bromo-diethyl-acetyl-urea and 130 parts. wt. propionic anhydride with 20 parts sulfuric acid, within 40 minutes. After cooling, it is mixed with 1000 parts. wt. chilled water and the separated crystal mass is extracted. It is purified by recrystallization from benzene or dilute alcohol. Propionyl-bromo-diethyl-acetyl-urea forms colorless crystals with a bitter taste. They are easily soluble in alcohol and benzene, slightly soluble in water. 103 ° melting point. Instead of propionic anhydride, benzoic anhydride can be used. The product thus obtained melts at 139-140 °. PL
Claims (1)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PL434B1 true PL434B1 (en) | 1924-08-30 |
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