4-[(5-chloro-2-oxo-2H-benzothiazol-3-yl)acetyl]piperazine-1-ethanol monohydrochloride Property

Melting point:

159-161°

Water Solubility 

Completely soluble in water

form 

powder to crystal

color 

White to Orange to Green

Merck 

14,9424

Safety

RTECS 

TL7050000

HS Code 

2934.20.8000

Toxicity

LD50 in male mice, rats (mg/kg): 178, 203 i.v.; 298, 540 i.p.; 564, 3600 orally (Watanabe)

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H318Causes serious eye damage

Precautionary statements

P280Wear protective gloves/protective clothing/eye protection/face protection.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P310Immediately call a POISON CENTER or doctor/physician.

P403Store in a well-ventilated place.

4-[(5-chloro-2-oxo-2H-benzothiazol-3-yl)acetyl]piperazine-1-ethanol monohydrochloride Chemical Properties,Usage,Production

Originator

Solantal,Fujisawa,Japan,1975

Uses

Tiaramide Hydrochloride is a useful compound for treatment of gastrointestinal disease.

Definition

ChEBI: Tiaramide hydrochloride 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