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CAS No.: | 77-36-1 |
---|---|
Name: | Chlortalidone |
Article Data: | 13 |
Molecular Structure: | |
Formula: | C14H11ClN2O4S |
Molecular Weight: | 338.771 |
Synonyms: | Benzenesulfonamide,2-chloro-5-(1-hydroxy-3-oxo-1-isoindolinyl)- (6CI,8CI);1-Oxo-3-(3-sulfamyl-4-chlorophenyl)-3-hydroxy-isoindolinum;2-Chloro-5-(1-hydroxy-3-oxo-1-isoindolinyl)benzenesulfonamide;2-Chloro-5-(3-hydroxy-1-oxoisoindol-3-yl)benzenesulfonamide;3-(4'-Chloro-3'-sulfamoylphenyl)-3-hydroxyphthalimidine;3-Hydroxy-3-[4-chloro-3-sulfamylphenyl]phthalimidine;Chlorothalidone;Chlorthalidon;Demi-Regroton;G 33182;Hygroton;Igroton;Isoren;NSC 69200;Natriuran;Oradil;Oxodolin;Phthalamudine;Racemicchlorthalidone;Renon;Saluretin;Thalitone;Zambesil; |
EINECS: | 201-022-5 |
Density: | 1.601 g/cm3 |
Melting Point: | 265-267 °C (dec.) |
Solubility: | slightly soluble in water, ethanol, chloroform, soluble in hot ethanol |
Appearance: | white solid |
Safety: | 22-24/25 |
PSA: | 117.87000 |
LogP: | 3.03410 |
chlorthalidon
Conditions | Yield |
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With dihydrogen peroxide; sodium hydroxide In water at 0 - 26℃; | 76% |
(-)-Chlortalidon
chlorthalidon
Conditions | Yield |
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With buffer solution In 1,4-dioxane half time of racemization; |
chlorthalidon
Conditions | Yield |
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With chloroform; ammonia |
chloroform
2-chloro-5-(1-chloro-3-oxo-phthalan-1-yl)-benzenesulfonyl chloride
ammonia
chlorthalidon
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1.1: zinc; acetic acid / 70 - 75 °C 2.1: chlorosulfonic acid / 0 - 80 °C 2.2: 2 h / 75 - 80 °C 3.1: ammonium hydroxide / acetone; water / 0 - 5 °C 4.1: dihydrogen peroxide; sodium hydroxide / water / 0 - 26 °C View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1.1: sodium hydroxide; hydroxylamine hydrochloride / methanol / 25 - 65 °C 2.1: zinc; acetic acid / 70 - 75 °C 3.1: chlorosulfonic acid / 0 - 80 °C 3.2: 2 h / 75 - 80 °C 4.1: ammonium hydroxide / acetone; water / 0 - 5 °C 5.1: dihydrogen peroxide; sodium hydroxide / water / 0 - 26 °C View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: chlorosulfonic acid / 0 - 80 °C 1.2: 2 h / 75 - 80 °C 2.1: ammonium hydroxide / acetone; water / 0 - 5 °C 3.1: dihydrogen peroxide; sodium hydroxide / water / 0 - 26 °C View Scheme |
Conditions | Yield |
---|---|
With zinc perchlorate In water at 20 - 110℃; for 30h; Autoclave; | 67% |
chlorthalidon
A
3-(4'-chlorophenyl)-1-isoindolinone
B
2-[(hydroxyamino)carbonyl]benzoic acid
C
3-phenyl-2,3-dihydro-isoindol-1-one
Conditions | Yield |
---|---|
With oxygen In methanol at 20℃; for 72h; Product distribution; Quantum yield; Further Variations:; Reagents; sensitizers and scavengers; Decomposition; photolysis; UV-irradiation; | A 46% B 12% C 42% |
Conditions | Yield |
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With sodium hydroxide |
The IUPAC name of Chlorphthalidolone is 2-chloro-5-(1-hydroxy-3-oxo-2H-isoindol-1-yl)benzenesulfonamide. With the CAS registry number 77-36-1, it is also named as 1-Keto-3-(3'-sulfamyl-4'-chlorophenyl)-3-hydroxyisoindoline. The product's categories are Amines; Heterocycles; Intermediates & Fine Chemicals; Pharmaceuticals; Sulfur & Selenium Compounds; CHForensic and Veterinary Standards; Alphabetic; Drugs & Metabolites; Neat Compounds. It is white solid which is slightly soluble in water, ethanol, chloroform, soluble in hot ethanol. When using it, people should not breathe dust and avoid contact with skin and eyes. Additionally, this chemical should be sealed in the container and stored in the cool and dry place.
The other characteristics of this product can be summarized as: (1)ACD/LogP: -0.74; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -0.74; (4)ACD/LogD (pH 7.4): -0.74; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 9.41; (8)ACD/KOC (pH 7.4): 9.35; (9)#H bond acceptors: 6; (10)#H bond donors: 4; (11)#Freely Rotating Bonds: 3; (12)Polar Surface Area: 75.3 Å2; (13)Index of Refraction: 1.694; (14)Molar Refractivity: 81.24 cm3; (15)Molar Volume: 211.5 cm3; (16)Polarizability: 32.2×10-24 cm3; (17)Surface Tension: 72.7 dyne/cm; (18)Rotatable Bond Count: 2; (19)Tautomer Count: 2; (20)Exact Mass: 338.012805; (21)MonoIsotopic Mass: 338.012805; (22)Topological Polar Surface Area: 118; (23)Heavy Atom Count: 22; (24)Complexity: 564.
Preparation of Chlorphthalidolone: It can be obtained by diazotization, metathesis, chlorosulfonation, cyclization, amination of 2-(3-Amino-4-chlorobenzoyl) benzoic acid.
Uses of Chlorphthalidolone: It is a diuretic drug used to treat hypertension. And it has the longest duration of action, but a similar diuretic effect at maximal therapeutic doses compared with with other medications of the thiazide class. What's more, this chemical is often used in the management of hypertension and edema. In addition, it can be used to produce 3-(4-chloro-phenyl)-2,3-dihydro-isoindol-1-one, phthalomonohydroxamic acid and 3-phenyl-2,3-dihydro-isoindol-1-one. This reaction needs reagent O2 and solvent methanol at temperature of 20 °C and under UV-irradiation. The reaction time is 71 hours. The yield is 12%.
People can use the following data to convert to the molecule structure.
1. SMILES:O=S(=O)(N)c1c(Cl)ccc(c1)C2(O)c3ccccc3C(=O)N2
2. InChI:InChI=1/C14H11ClN2O4S/c15-11-6-5-8(7-12(11)22(16,20)21)14(19)10-4-2-1-3-9(10)13(18)17-14/h1-7,19H,(H,17,18)(H2,16,20,21)
The following are the toxicity data which has been tested.
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
guinea pig | LD50 | oral | > 5gm/kg (5000mg/kg) | Drugs in Japan Vol. 6, Pg. 249, 1982. | |
human | TDLo | oral | 2587ug/kg/8D- (2.587mg/kg) | SENSE ORGANS AND SPECIAL SENSES: OTHER: EYE BEHAVIORAL: HEADACHE GASTROINTESTINAL: NAUSEA OR VOMITING | JAMA, Journal of the American Medical Association. Vol. 258, Pg. 484, 1987. |
man | TDLo | oral | 5714ug/kg/4D- (5.714mg/kg) | VASCULAR: BP ELEVATION NOT CHARACTERIZED IN AUTONOMIC SECTION ENDOCRINE: HYPERGLYCEMIA BLOOD: OTHER CHANGES | JAMA, Journal of the American Medical Association. Vol. 220, Pg. 1592, 1972. |
mouse | LD50 | oral | > 5gm/kg (5000mg/kg) | Drugs in Japan Vol. 6, Pg. 249, 1982. | |
mouse | LD50 | subcutaneous | > 5gm/kg (5000mg/kg) | Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 9, Pg. 759, 1967. | |
rabbit | LD50 | oral | > 5gm/kg (5000mg/kg) | Drugs in Japan Vol. 6, Pg. 249, 1982. | |
rat | LD50 | oral | > 5gm/kg (5000mg/kg) | Drugs in Japan Vol. 6, Pg. 249, 1982. | |
rat | LD50 | subcutaneous | > 5gm/kg (5000mg/kg) | Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 9, Pg. 759, 1967. | |
women | TDLo | oral | 12mg/kg/6D-I (12mg/kg) | Southern Medical Journal. Vol. 79, Pg. 629, 1986. | |
women | TDLo | oral | 12mg/kg/6D-I (12mg/kg) | Southern Medical Journal. Vol. 79, Pg. 629, 1986. |