| Identification | Back Directory | [Name]
chlorthenoxazine | [CAS]
132-89-8 | [Synonyms]
Ap 67
Apirazin
Ossazone
Piroxina
Valmorin
Valtorin
chlorthenoxazin
chlorthenoxazine
Chlorethylbenzmethoxazone
2-(2-chloroethyl)-2,3-dihydro-1,3-benzoxazin-4-one
4H-1,3-Benzoxazin-4-one,2-(2-chloroethyl)-2,3-dihydro-
2-(2-chloroethyl)-2,3-dihydro-4H-benzo[e][1,3]oxazin-4-one | [EINECS(EC#)]
205-082-3 | [Molecular Formula]
C10H10ClNO2 | [MDL Number]
MFCD00012095 | [MOL File]
132-89-8.mol | [Molecular Weight]
211.64 |
| Chemical Properties | Back Directory | [Melting point ]
146-147° (dec) | [Boiling point ]
303°C (rough estimate) | [density ]
1.2414 (rough estimate) | [refractive index ]
1.5500 (estimate) | [storage temp. ]
Store at -20°C | [solubility ]
Soluble in DMSO | [pka]
12.70±0.40(Predicted) |
| Hazard Information | Back Directory | [Originator]
Reugaril ,Farber ,Italy ,1966 | [Definition]
ChEBI: Chlorthenoxazine is a benzoxazine. | [Manufacturing Process]
A mixture of 4 liters chloroform and 1,050 cc ethanol was saturated with dry
hydrogen chloride gas at -5°C to +5°C in a vessel having a net volume of 15
liters and provided with a stirring device, reflux cooler, gas feed line,
thermometer and dropping funnel. 455 g acrolein which had been precooled
to 0°C were added dropwise to the solution over a period of 1 to 2 hours
while maintaining the temperature below +5°C and vigorously stirring. 1,070
g salicylamide and 1,080 g glacial acetic acid were added to the resulting
solution of beta-chloropropionaldehyde acetal, thereby forming a suspension
which was heated to 60°C while stirring. A clear solution was formed which
was maintained at 60°C for an additional hour. The solution was allowed to
cool to about 40°C and was then washed with water by passing a strong
stream of water under the surface of the chloroform and continuously
withdrawing the upper phase. When the water had reached a pH of 3-4, the
precipitated reaction product was separated by vacuum filtration. The
chloroform phase of the filtrate was evaporated under a weak vacuum and the
residue was combined with the precipitate first obtained. The combined
products were stirred with 2 liters of a 5% sodium hydroxide solution. The raw
reaction product was then washed with water, dried and recrystallized from
ethanol. The product had the melting point of 146°C to 147°C
(decomposition). The yield was 1,260 g, corresponding to 76% of the
theoretical yield. | [Therapeutic Function]
Antipyretic, Analgesic |
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