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| 5-[2-(DIETHYLAMINO)ETHYL]-3-PHENYL-1,2,4-OXADIAZOLE CITRATE SALT Basic information |
| Product Name: | 5-[2-(DIETHYLAMINO)ETHYL]-3-PHENYL-1,2,4-OXADIAZOLE CITRATE SALT | | Synonyms: | OXOLAMINE CITRATE;OXOLAMINE CITRATE SALT;2,4-oxadiazole,5-(2-(diethylamino)ethyl)-3-phenyl-citrate;3-phenyl-5-(beta-(diethylamino)ethyl)-1,2,4-oxadiazolecitrate;5-beta-diethylaminoethyl-3-phenyl-1,2,4-oxadiazolecitrate;OxolaminCitrate;5-[2-(DIETHYLAMINO)ETHYL]-3-PHENYL-1,2,4-OXADIAZOLE CITRATE;5-[2-(DIETHYLAMINO)ETHYL]-3-PHENYL-1,2,4-OXADIAZOLE CITRATE SALT | | CAS: | 1949-20-8 | | MF: | C20H27N3O8 | | MW: | 437.44 | | EINECS: | 217-760-6 | | Product Categories: | | Mol File: | 1949-20-8.mol |
| 5-[2-(DIETHYLAMINO)ETHYL]-3-PHENYL-1,2,4-OXADIAZOLE CITRATE SALT Chemical Properties |
| Melting point | 141-142 °C | | storage temp. | 2-8°C | | solubility | DMSO (Slightly), Methanol (Slightly, Heated) | | form | Solid | | color | Crystals. Sltly sol in water and alc |
| Hazard Codes | Xn | | Risk Statements | 22 | | Safety Statements | 36 | | WGK Germany | 3 | | RTECS | RO0720000 | | Toxicity | TDLo orl-rat: 15 g/kg/1Y-I:CAR EMPSAL 2,1,63 orl-rat LD50:1650 mg/kg BJPCAL 16,209,61 |
| 5-[2-(DIETHYLAMINO)ETHYL]-3-PHENYL-1,2,4-OXADIAZOLE CITRATE SALT Usage And Synthesis |
| Originator | Bredon,Organon | | Uses | Antiinflammatory | | Uses | Oxolamine Citrate, is a antiinflammatory drug used as a cough suppressant. | | Manufacturing Process | 18.7 g 3-chloro-propionyl chloride in 50 ml of dry ether was added dropwise with stirring to the cooled with ice solution 40 g of N-hydroxybenzamidine in 450 ml dry ester. A dense precipitate had fallen. The mixture was stirred 0.5 hour at room temperature and then was filtered off. The precipitate was thoroughly washed with water for a removal hydrochloride of starting Nhydroxybenzamidine whereas N-(amino)phenylmethylene-3-Cl-propionamide didnt solve. It was dried in vacuum over P2O5. Yield of clean product 94% from theoretical. MP: 98°-99°C. The solution of 9.2 g diethyl amine in 50 ml dry benzene was added dropwise to a suspension of above prepared N(amino)phenylmethylene-3-Cl-propionamide in dry benzene with stirring and cooling.
The mixture was warmed and stirred else 2 hours after adding. Then it was cooled, washed two times with water and dried over CaCl2. Then the solvent was removed. The residue was distilled in vacuum. Diethyl-[2-(3phenyl[1,2,4]oxadiasol-5)ethyl]amine (oxolamine) had BP: 127°C/0.4 mm. Yield 10.5 g.
| | Therapeutic Function | Antitussive, Antiinflammatory | | Safety Profile | Poison by intraperitoneal route. Moderately toxic by ingestion. Experimental teratogenic and reproductive effects. Questionable carcinogen with experimental carcinogenic data. When heated to decomposition it emits toxic fumes of NOx. See also AMINES and other oxolamhe entries |
| 5-[2-(DIETHYLAMINO)ETHYL]-3-PHENYL-1,2,4-OXADIAZOLE CITRATE SALT Preparation Products And Raw materials |
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![5-[2-(DIETHYLAMINO)ETHYL]-3-PHENYL-1,2,4-OXADIAZOLE CITRATE SALT](/img/1949-20-8.jpg "5-[2-(DIETHYLAMINO)ETHYL]-3-PHENYL-1,2,4-OXADIAZOLE CITRATE SALT")
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