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ChemicalBook--->CAS DataBase List--->959-14-8

959-14-8

959-14-8 Structure

959-14-8 Structure
IdentificationMore
[Name]

Oxolamine
[CAS]

959-14-8
[Synonyms]

5-[2-(diethylamino)ethyl]-3-phenyl-1,2,4-oxadiazole
OXOLAMINE
1,2,4-OXADIAZOLE,5-(2-DIETHYLAMINO)ETHYL)-3-PHENYL-
Oxolamine (base and/or unspecified salts)
683 M
683M
AF-438
[EINECS(EC#)]

213-493-4
[Molecular Formula]

C14H19N3O
[MDL Number]

MFCD00866857
[Molecular Weight]

245.32
[MOL File]

959-14-8.mol
Chemical PropertiesBack Directory
[Melting point ]

25°C
[Boiling point ]

bp0.4 127°
[density ]

1.0516 (rough estimate)
[refractive index ]

1.5310 (estimate)
[form ]

Liquid
[pka]

9.40±0.25(Predicted)
[LogP]

2.393
[CAS DataBase Reference]

959-14-8(CAS DataBase Reference)
Hazard InformationBack Directory
[Originator]

Bredon,Organon
[Uses]

Oxolamine is a antiinflammatory drug used as a cough suppressant.
[Definition]

ChEBI: N,N-diethyl-2-(3-phenyl-1,2,4-oxadiazol-5-yl)ethanamine is an oxadiazole and a ring assembly.
[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]

Moderately toxic by ingestion and subcutaneous routes. When heated to decomposition it emits toxic fumes of NOx.
Safety DataBack Directory
[Toxicity]

LD50 oral in rat: > 2gm/kg
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