32527-55-2

Basic information

• Product Name: Tiaramide
• Synonyms: Tiaramide;4-[(5-Chloro-2-oxobenzothiazol-3-yl)acetyl]-1-piperazineethanol;5-Chloro-3-[[4-(2-hydroxyethyl)-1-piperazinyl]carbonylmethyl]-2,3-dihydrobenzothiazol-2-one;NTA-194;4-[(5-Chloro-2-oxo-3(2H)-benzothiazolyl)acetyl]piperazine-1-ethanol;1-Piperazineethanol, 4-((5-chloro-2-oxo-3(2H)-benzothiazolyl)acetyl)- (9ci);1-Piperazineethanol, 4-((5-chloro-2-oxo-3-benzothiazolinyl)acetyl)-;35941-71-0 (Mono-hydrochloride)
• CAS NO: 32527-55-2
• Molecular Formula: C₁₅H₁₈ClN₃O₃S
• Molecular Weight: 355.84
• EINECS: 251-083-7
• Mol File: 32527-55-2.mol
• Article Data: 1

Chemical Properties

• Melting Point: 159-161 °C
• Boiling Point: 605.8°Cat760mmHg
• Flash Point: 320.2°C
• Appearance: /
• Density: 1.432g/cm³
• Vapor Pressure: 1.58E-15mmHg at 25°C
• Refractive Index: 1.64
• PKA: 6.2(at 25℃)
• CAS DataBase Reference: Tiaramide(CAS DataBase Reference)
• NIST Chemistry Reference: Tiaramide(32527-55-2)
• EPA Substance Registry System: Tiaramide(32527-55-2)

Safety Data

• Hazardous Substances Data: 32527-55-2(Hazardous Substances Data)

Usage

Originator

Solantal,Fujisawa,Japan,1975

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

InChI:InChI=1/C15H18ClN3O3S/c16-11-1-2-13-12(9-11)19(15(22)23-13)10-14(21)18-5-3-17(4-6-18)7-8-20/h1-2,9,20H,3-8,10H2

Upstream product

• 103-76-4 1-(2-hydroxyethyl)piperazine 
• 54769-25-4 2-(5-chloro-2-oxo-2,3-dihydro-1,3-benzothiazol-3-yl)acetic acid 
• 54769-22-1 1-methanesulfonyloxy-1,2,3-benzotriazole 

Relevant articles and documents

Sulfonic acid esters

A novel process for the amidation or esterification which comprises reacting a compound having a carboxy group with a compound having an amino or imino group which can be acylated or with a compound having a hydroxy group in the presence of a sulfonic acid ester of the formula: wherein R1 is an organic group and R2 O-- is a residue of a strongly acidic N-hydroxy compound as a condensation agent, and a novel sulfonic acid ester useful as such a condensation agent and a process for the preparation thereof.