Tiaramide
- CAS NO.:32527-55-2
- Empirical Formula: C15H18ClN3O3S
- Molecular Weight: 355.84
- MDL number: MFCD00864788
- EINECS: 251-083-7
- SAFETY DATA SHEET (SDS)
- Update Date: 2023-05-04 17:34:37
What is Tiaramide?
Originator
Solantal,Fujisawa,Japan,1975
Definition
ChEBI: Tiaramide is a member of benzothiazoles.
Manufacturing Process
A solution of ethyl 5-chloro-2-oxo-3-benzo-thiazolineacetate (4.0 grams) in 1- (2-hydroxyethyl)piperazine is heated at 100°C for 24 hours. After cooling, the resulting mixture is extracted with chloroform. The chloroform extract is washed with water and shaken with 10% hydrochloric acid. The hydrochloric acid layer is washed with chloroform, made alkaline with 10% sodium hydroxide solution and extracted with chloroform. The chloroform extract is washed with water, dried over magnesium sulfate and concentrated. The residual oil (5.5 grams) is allowed to stand to form crystals, which are recrystallized from a mixture of ethyl acetate (40 ml) and ethanol (15 ml) to give 3-[4-(2-hydroxyethyl)-1-piperazinylcarbonylmethyl]-5-chloro-2(3H)- benzothiazolinone (3.2 grams) as colorless crystals, MP 159° to 161°C. The following is an alternate method of preparation: A mixture of 3-(1- piperazinyl)carbonylmethyl-5-chloro-2(3H)-benzothiazolinone (500 mg), anhydrous potassium carbonate (400 mg), 2-hydroxyethyl bromide (300 mg) and anhydrous ethanol (20 ml) is heated while refluxing for 5 hours. The reaction mixture is concentrated under reduced pressure. The residue is extracted with chloroform. The chloroform layer is dried over magnesium sulfate and concentrated. The residue is crystallized from a mixture of ethyl acetate and ethanol to give 3-[4-(2-hydroxyethyl]-1- piperazinylcarbonylmethyl]-5-chloro-2(3H)-benzothiazolinone (370 mg) as crystals, MP 159° to 160°C.
Therapeutic Function
Antiinflammatory
Properties of Tiaramide
Melting point: | 159-161 °C |
Boiling point: | 605.8±65.0 °C(Predicted) |
Density | 1.432±0.06 g/cm3(Predicted) |
pka | 6.2(at 25℃) |
Safety information for Tiaramide
Computed Descriptors for Tiaramide
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