Name: Chlortalidone
SKU: 77-36-1

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Basic Information

Molecular Structure:
CAS No.:	77-36-1
Name:	Chlortalidone

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

Synthetic route

: 3-(3'-sulfamyl-4'-chlorophenyl)phthalimidine

: 77-36-1
chlorthalidon

Conditions

Conditions	Yield
With dihydrogen peroxide; sodium hydroxide In water at 0 - 26℃;	76%

: 77-36-1, 74658-80-3, 74658-81-4, 74666-82-3
(-)-Chlortalidon

: 77-36-1
chlorthalidon

Conditions

Conditions	Yield
With buffer solution In 1,4-dioxane half time of racemization;

(+-)-2-chloro-5-<1-chloro-3-oxo-phthalan-1-yl>-benzenesulfonyl chloride: (+-)-2-chloro-5-<1-chloro-3-oxo-phthalan-1-yl>-benzenesulfonyl chloride

: 77-36-1
chlorthalidon

Conditions

Conditions	Yield
With chloroform; ammonia

: 67-66-3
chloroform

: 68592-11-0
2-chloro-5-(1-chloro-3-oxo-phthalan-1-yl)-benzenesulfonyl chloride

: 7664-41-7
ammonia

: 77-36-1
chlorthalidon

...Expand

: 2224-83-1
4-(4-chlorophenyl)-1H-2,3-benzoxazin-1-one

: 77-36-1
chlorthalidon

Conditions

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

: 85-56-3
2-(4-chlorobenzoyl)benzoic acid

: 77-36-1
chlorthalidon

Conditions

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

: 2224-77-3
3-(4'-chlorophenyl)-1-isoindolinone

: 77-36-1
chlorthalidon

Conditions

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

: 64-17-5
ethanol

: 77-36-1
chlorthalidon

: 2-chloro-5-(1-ethyl-3-oxo-1-Isoindolinyl)benzenesulfonamide

Conditions

Conditions	Yield
With zinc perchlorate In water at 20 - 110℃; for 30h; Autoclave;	67%

: 77-36-1
chlorthalidon

A: 2224-77-3
3-(4'-chlorophenyl)-1-isoindolinone

B: 17698-09-8
2-[(hydroxyamino)carbonyl]benzoic acid

C: 835-18-7
3-phenyl-2,3-dihydro-isoindol-1-one

Conditions

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%

...Expand

: 77-36-1
chlorthalidon

: 5270-74-6
2-(4-chloro-3-sulfamoyl-benzoyl)-benzoic acid

Conditions

Conditions	Yield
With sodium hydroxide

Raw Materials

68592-11-0

77-36-1

7664-41-7

67-66-3

Downstream Products

77-36-1

835-18-7

17698-09-8

2224-77-3

5270-74-6

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Specification

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.

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