flumethiazide
flumethiazide Basic information
- Product Name:
- flumethiazide
- Synonyms:
-
- 6-Trifluoromethyl-7-sulfamoyl-4H-1,2,4-benzothiazine 1,1-dioxide
- Ademol
- Fludemil
- Routrax
- Trifluoromethylthiazide
- flumethiazide
- 2H-1,2,4-Benzothiadiazine-7-sulfonamide, 6-(trifluoromethyl)-, 1,1-dioxide
- NSC 44626
- CAS:
- 148-56-1
- MF:
- C8H6F3N3O4S2
- MW:
- 329.278
- EINECS:
- 2057174
- Mol File:
- 148-56-1.mol
flumethiazide Chemical Properties
- Melting point:
- 306.6°C
- Boiling point:
- 560.0±60.0 °C(Predicted)
- Density
- 1.6578 (estimate)
- pka
- pKa 6.3(H2O) (Uncertain)
- Water Solubility
- 1.05g/L(room temperature)
Safety Information
- Hazardous Substances Data
- 148-56-1(Hazardous Substances Data)
flumethiazide Usage And Synthesis
Originator
Ademol,Squibb,US,1959
Definition
ChEBI: Flumethiazide is a benzothiadiazine.
Manufacturing Process
Chilled 3-trifluoromethylaniline (32.2 g) is added dropwise over a 45-minute
period to 150 ml of chlorosulfonic acid with stirring and cooling. The ice bath
is removed and 140 g of sodium chloride is added over 3 hours. The mixture
is heated on a water bath for 30 minutes, then gradually up to 160°C over 6
hours. The cooled reaction mixture is diluted with 500 ml of an ice water
slurry and taken into ether. The ether is dried and evaporated to leave 5-
trifluoromethylamine-2,4-disulfonyl chloride.
The crude residue is heated on the steam bath for 1 hour with 75 ml of
concentrated ammonium hydroxide. Cooling and filtration gives 2,4-
disulfamyl-5-trifluoromethylaniline, MP 241°C to 243°C.
This intermediate is treated with an excess of 98% formic acid at steam bath
temperature for 3 hours. Evaporation and dilution with water gives 7-sulfamyl-
6-trifluoromethyl-1,2,4-benzothiadiazine-1,1-dioxide, MP 304°C to 308°C.
Therapeutic Function
Carbonic anhydrase inhibitor