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4-(3'-Methylphenyl)amino-3-pyridinesulfonamide
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Name

4-(3'-Methylphenyl)amino-3-pyridinesulfonamide

 EINECS 615-805-8
CAS No. 72811-73-5 Density 1.357 g/cm3
PSA 93.46000 LogP 3.63510
Solubility N/A Melting Point 162-164oC
Formula C12H13N3O2S Boiling Point 475.8 °C at 760 mmHg
Molecular Weight 263.32 Flash Point 241.5 °C
Transport Information N/A Appearance N/A
Safety 26 Risk Codes 36
Molecular Structure Molecular Structure of 72811-73-5 (4-(3'-Methylphenyl)amino-3-pyridinesulfonamide) Hazard Symbols Xi
Synonyms

3-Sulfonamido-4-(3-methylanilino)pyridine;BM 960102;4-(3-methylphenyl)amino-3-pyridine sulfonamide;

Article Data 5

4-(3'-Methylphenyl)amino-3-pyridinesulfonamide Synthetic route

33263-43-3

4-chloropyridine-3-sulphonamide

108-44-1

1-amino-3-methylbenzene

72811-73-5

3-sulfonamido-4-(3'-methylphenyl) aminopyridine

Conditions
ConditionsYield
In methanol at 39.85℃; for 3h;96.5%
In propan-1-ol for 5h; Heating;
In water at 80 - 90℃; for 1 - 1.5h; Product distribution / selectivity;
Stage #1: 4-chloropyridine-3-sulphonamide; 1-amino-3-methylbenzene In water for 0.5h; Heating / reflux;
Stage #2: With sodium hydroxide In water at 20 - 35℃;
Stage #3: With sulfuric acid In water Product distribution / selectivity;
777854-85-0

4-chloro-3-pyridinesulfonamide hydrochloride

108-44-1

1-amino-3-methylbenzene

72811-73-5

3-sulfonamido-4-(3'-methylphenyl) aminopyridine

Conditions
ConditionsYield
Stage #1: 4-chloro-3-pyridinesulfonamide hydrochloride; 1-amino-3-methylbenzene In water at 90℃; for 3h;
Stage #2: With sodium hydrogencarbonate In water at 20℃; pH=7 - 8;		92%
625-95-6

3-Iodotoluene

75903-62-7

3-sulfonamido-4-aminopyridine

72811-73-5

3-sulfonamido-4-(3'-methylphenyl) aminopyridine

Conditions
ConditionsYield
With copper; potassium carbonate In butan-1-ol53.1%
72811-73-5

3-sulfonamido-4-(3'-methylphenyl) aminopyridine

1795-48-8

Isopropyl isocyanate

torasemide crude

torasemide crude

Conditions
ConditionsYield
Stage #1: 3-sulfonamido-4-(3'-methylphenyl) aminopyridine With sodium hydride In tetrahydrofuran; toluene at 5 - 20℃; for 16h;
Stage #2: Isopropyl isocyanate In tetrahydrofuran; toluene at 20℃;
Stage #3: Isopropyl isocyanate With sodium hydride; acetic acid more than 3 stages;		100%
72811-73-5

3-sulfonamido-4-(3'-methylphenyl) aminopyridine

1795-48-8

Isopropyl isocyanate

56211-40-6

torasemide

Conditions
ConditionsYield
Stage #1: 3-sulfonamido-4-(3'-methylphenyl) aminopyridine; Isopropyl isocyanate With potassium carbonate In diethylene glycol dimethyl ether; water at 65 - 70℃; for 0.583333h;
Stage #2: With acetic acid In diethylene glycol dimethyl ether; water at 20 - 25℃; for 3h; pH=5.3 - 5.7;		96.5%
Stage #1: 3-sulfonamido-4-(3'-methylphenyl) aminopyridine; Isopropyl isocyanate With sodium hydroxide In acetone at 20 - 30℃;
Stage #2: With acetic acid In water; acetone at 20 - 25℃; for 0.25h; pH=5.3 - 5.7;		96%
Stage #1: 3-sulfonamido-4-(3'-methylphenyl) aminopyridine; Isopropyl isocyanate With sodium hydroxide In acetone at 20 - 30℃;
Stage #2: With acetic acid In water; acetone at 20 - 25℃; for 0.25h; pH=5.5;		96%
72811-73-5

3-sulfonamido-4-(3'-methylphenyl) aminopyridine

1795-48-8

Isopropyl isocyanate

torsemide sodium

Conditions
ConditionsYield
With sodium hydroxide In acetone at 5 - 20℃; for 2h; Reagent/catalyst;94.5%
17614-10-7

phenyl N-isopropylcarbamate

72811-73-5

3-sulfonamido-4-(3'-methylphenyl) aminopyridine

56211-40-6

torasemide

Conditions
ConditionsYield
Stage #1: phenyl N-isopropylcarbamate; 3-sulfonamido-4-(3'-methylphenyl) aminopyridine With triethylamine In water; acetone for 3h; Heating / reflux;
Stage #2: With sodium hydroxide In water at 20 - 25℃;
Stage #3: With sulfuric acid In water; acetone at 50 - 55℃; for 1h; Product distribution / selectivity;		87.8%
Stage #1: phenyl N-isopropylcarbamate; 3-sulfonamido-4-(3'-methylphenyl) aminopyridine With sodium hydroxide In water at 90 - 100℃; for 5h;
Stage #2: With sulfuric acid In water at 20 - 70℃; for 1h; Product distribution / selectivity;		85%
Stage #1: 3-sulfonamido-4-(3'-methylphenyl) aminopyridine With sodium hydroxide In water at 20 - 35℃;
Stage #2: phenyl N-isopropylcarbamate In water; acetone at 50 - 60℃; for 20h;
Stage #3: With sulfuric acid In water at 15 - 50℃; for 3h; pH=7.0; Product distribution / selectivity;
541-41-3

chloroformic acid ethyl ester

72811-73-5

3-sulfonamido-4-(3'-methylphenyl) aminopyridine

72810-57-2

[4-(3-methyl-anilino)-pyridine-3-sulfonyl]-carbamic acid ethyl ester

Conditions
ConditionsYield
With pyridine for 0.333333h; Heating;75%
In tetrahydrofuran for 8h; Ambient temperature;
72811-73-5

3-sulfonamido-4-(3'-methylphenyl) aminopyridine

5848-27-1

N-cyano-N'-isopropyl-S-methylcarbamimidothioate

N2-cyano-N1-isopropyl-N3-<4-(3-methylphenylamino)-3-pyridylsulfonyl>guanidine

Conditions
ConditionsYield
With sodium hydroxide In 1,4-dioxane; N,N-dimethyl-formamide for 6h; Heating;37%
72811-73-5

3-sulfonamido-4-(3'-methylphenyl) aminopyridine

C23H28N4O3S

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 75 percent / pyridine / 0.33 h / Heating
2: 37 percent / toluene / 5 h / Heating
View Scheme

4-(3'-Methylphenyl)amino-3-pyridinesulfonamide Chemical Properties

Empirical Formula: C12H13N3O2S
Molecular Weight: 263.3155g/mol
Structure of 3-Pyridinesulfonamide,4-[(3-methylphenyl)amino]- (CAS NO.72811-73-5):

Index of Refraction: 1.641
Molar Refractivity: 69.97 cm3
Molar Volume: 193.9 cm3
Polarizability: 27.73×10-24cm3
Surface Tension: 63.3 dyne/cm
Density: 1.357 g/cm3
Flash Point: 241.5 °C
Enthalpy of Vaporization: 73.94 kJ/mol
Boiling Point: 475.8 °C at 760 mmHg
Vapour Pressure: 3.23E-09 mmHg at 25°C 
Product Categories: INTERMEDIATESOFTORASEMIDE;Pyridines derivates;(intermediate of torasemide);Pyridines;Torsemide 
Systematic Name: 4-[(3-methylphenyl)amino]pyridine-3-sulfonamide
SMILES: O=S(=O)(c2c(Nc1cc(ccc1)C)ccnc2)N
InChI: InChI=1/C12H13N3O2S/c1-9-3-2-4-10(7-9)15-11-5-6-14-8-12(11)18(13,16)17/h2-8H,1H3,(H,14,15)(H2,13,16,17)
InChIKey: ZXPCUGWAKUIOOF-UHFFFAOYAX

4-(3'-Methylphenyl)amino-3-pyridinesulfonamide Specification

  3-Pyridinesulfonamide,4-[(3-methylphenyl)amino]- , its cas register number is 72811-73-5. It also can be called ; 4-[(3-Methylphenyl)amino]pyridine-3-sulfonamide ; 3-Sulfonamido-4-(3-methylanilino)pyridine ; 4-(3-Methylphenyl)amino-3-Pyridine Sulfonamide ; 4-(3-toluidino)pyridine-3-sulfonamide .

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