6-ETHOXY-2-BENZOTHIAZOLESULFONAMIDE

6-ETHOXY-2-BENZOTHIAZOLESULFONAMIDE Basic information
Product Name:6-ETHOXY-2-BENZOTHIAZOLESULFONAMIDE
Synonyms:6-ETHOXYZOLAMIDE;6-ETHOXY-2-BENZOTHIAZOLESULFONAMIDE;ETHOXZOLAMIDE;2-Benzothiazolesulfonamide, 6-ethoxy-;6-Ethoxy-1,3-benzothiazole-2-sulfonamide;L-643786;PNU-4191;6-ethoxy-2-benzothiazolesulfonamid
CAS:452-35-7
MF:C9H10N2O3S2
MW:258.32
EINECS:207-199-5
Product Categories:ANTIZOL
Mol File:452-35-7.mol
6-ETHOXY-2-BENZOTHIAZOLESULFONAMIDE Structure
6-ETHOXY-2-BENZOTHIAZOLESULFONAMIDE Chemical Properties
Melting point 190-193 °C(lit.)
Boiling point 464.9±37.0 °C(Predicted)
density 1.4767 (rough estimate)
refractive index 1.6800 (estimate)
storage temp. Refrigerator
solubility DMSO (Slightly), Ethyl Acetate (Slightly)
form Solid
pkapKa 8.12(H2O t=25.0) (Uncertain)
color Off-White
Water Solubility 10.33mg/L(25 ºC)
Merck 13,3790
Safety Information
Hazard Codes Xi
Risk Statements 36/37/38
Safety Statements 26
WGK Germany 3
RTECS DL6390000
Hazardous Substances Data452-35-7(Hazardous Substances Data)
MSDS Information
ProviderLanguage
SigmaAldrich English
6-ETHOXY-2-BENZOTHIAZOLESULFONAMIDE Usage And Synthesis
OriginatorCardrase,Upjohn,US,1957
Usesalcohol dehydrogenase inhibitor, antidote
UsesEthoxzolamide is used in the treatment of glaucoma, and is also used as a diuretic, acting as a carbonic anhydrase inhibitor.
DefinitionChEBI: 1,3-Benzothiazole substituted a sulfonamide and an ethoxy group at positions 2 and 6, respectively. A carbonic anhydrase inhibitor, it has been used in the treatment of glaucoma, and as a diuretic.
Manufacturing ProcessPreparation of 6-Ethoxybenzothiazole-2-Sulfenamide: A solution prepared by dissolving 21.0 grams (0.1 mol) of 6-ethoxybenzothiazole-2-thiol, Sebrell and Boord, J. Am. Chem. Soc. 45: 2390 to 2399 (1923), in 75 ml of water containing 5 grams of sodium hydroxide, and 75 ml of 10% sodium hypochlorite solution were added simultaneously to 300 ml of concentrated ammonium hydroxide which was cooled to 0°C, and vigorously stirred. During the addition the temperature was not allowed to rise above 5°C. The resulting solid was recovered by filtration, washed thoroughly with water, and dried at room temperature under reduced pressure. There was obtained 21 grams of 6-ethoxybenzothiazole-2-sulfenamide melting at 132° to 155°C (decomposition). Recrystallization from ethyl acetate gave a product melting at 140.5° to 143°C (decomposition).
Preparation of 6-Ethoxybenzothiazole-2-Sulfonamide: A solution of 3.39 grams (0.015 mol) of the sulfenamide in 100 ml of acetone was treated dropwise, with stirring, with a solution of 3.5 grams of potassium permanganate in 100 ml of water. The temperature rose to 42°C. After stirring an additional 10 minutes the reaction mixture was filtered to remove manganese dioxide, the latter was washed with 100 ml of warm water, and the combined filtrates were concentrated under reduced pressure to remove acetone. The residual solution was treated with charcoal, filtered and acidified with concentrated hydrochloric acid. After standing in the refrigerator for 4 hours the solid sulfonamide was recovered by filtration, washed with water and dried. There was obtained 2.37 grams of 6-ethoxybenzothiazole-2-sulfonamide melting at 180° to 190°C. Recrystallization from ethyl acetate-Skellysolve B gave 1.25 grams of material melting at 188° to 190.5°C.
Therapeutic FunctionDiuretic, Cardiotonic, Smooth muscle relaxant, Respiratory stimulant
General Description6-Ethoxy-2-benzothiazolesulfonamide is a membrane permeable carbonic anhydrase inhibitor and its ocular disposition and pharmacology in normal albino rabbits has been investigated. It causes inhibition of insulin degradation in vitro.
Clinical UseEthoxzolamide is another carbonic anhydrase inhibitor with properties and uses resembling those of acetazolamide.
6-ETHOXY-2-BENZOTHIAZOLESULFONAMIDE Preparation Products And Raw materials
Raw materialsAmmonia-->6-ETHOXY-2-MERCAPTOBENZOTHIAZOLE-->Potassium permanganate-->Sodium hypochlorite
Thiabendazole Phthalylsulfathiazole SULFAMETHIZOLE Sulfathiazole 5-METHOXYBENZOTHIAZOLE ETHABOXAM 2-Mercaptothiazole 2-Mercaptobenzothiazole 6-Benzothiazolol(7CI,8CI,9CI) 6-ETHOXY-2-BENZOTHIAZOLESULFONAMIDE 6-METHOXY-1,3-BENZOTHIAZOLE 2-Benzothiazolesulfenamide(6CI,7CI,8CI,9CI) 6-ETHOXY-2-MERCAPTOBENZOTHIAZOLE

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