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115256-11-6

Basic Information
CAS No.: 115256-11-6
Name: Methanesulfonamide,N-[4-[2-[methyl[2-[4-[(methylsulfonyl)amino]phenoxy]ethyl]amino]ethyl]phenyl]-
Molecular Structure:
Molecular Structure of 115256-11-6 (Methanesulfonamide,N-[4-[2-[methyl[2-[4-[(methylsulfonyl)amino]phenoxy]ethyl]amino]ethyl]phenyl]-)
Formula: C19H27N3O5S2
Molecular Weight: 441.56
Synonyms: Dofetilida;Tikosyn;UK 68798;Dofetilidum;Tikosyn;UK 68,798;UNII-R4Z9X1N2ND;beta-((p-Methanesulfonamidophenethyl)methylamino)methanesulfono-p-phenetidide;CHEBI:4681;
EINECS: 638-817-5
Density: 1.344 g/cm3
Melting Point: 147-149 °C
Boiling Point: 614.1 °C at 760 mmHg
Flash Point: 325.2 °C
Solubility:
Appearance: white crystalline solid
Hazard Symbols: T,N
Risk Codes: 61-48/22-51
Safety: 53-22-36-57
Transport Information:
PSA: 121.57000
LogP: 4.29050
Synthetic route
124-63-0

methanesulfonyl chloride

115256-12-7

1-(4-methanesulphonamidophenoxy)-2-[N-methyl-N-(4-aminophenethyl)amino]ethane

115256-11-6

dofetilide

Conditions
ConditionsYield
With triethylamine In dichloromethane at 0℃; Mesylation;92.3%
3144-09-0

methanesulfonamide

1197186-15-4

N-(4-chlorophenethyl)-2-(4-chlorophenoxy)-N-methylethanamine

115256-11-6

dofetilide

Conditions
ConditionsYield
With bis(η3-allyl-μ-chloropalladium(II)); potassium carbonate; tert-butyl XPhos In 2-methyltetrahydrofuran at 80℃; Inert atmosphere;91%
115256-13-8

1-(4-aminophenoxy)-2-[N-(4-aminophenethyl)-N-methylamino]ethane

7143-01-3

Methanesulfonic anhydride

115256-11-6

dofetilide

Conditions
ConditionsYield
In dichloromethane Ambient temperature;51%
69447-84-3

p-nitrophenethylamine hydrobromide

115256-11-6

dofetilide

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 81.5 percent / K2CO3 / acetonitrile / Heating
2: 87.2 percent / HCO2H / Heating
3: 75 percent / Fe; HCl / ethanol / Heating
4: 92.3 percent / Et3N / CH2Cl2 / 0 °C
View Scheme

N-[4-(2-bromoethoxy)-phenyl]-methansulfonamide

115256-11-6

dofetilide

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 81.5 percent / K2CO3 / acetonitrile / Heating
2: 87.2 percent / HCO2H / Heating
3: 75 percent / Fe; HCl / ethanol / Heating
4: 92.3 percent / Et3N / CH2Cl2 / 0 °C
View Scheme
115256-44-5

1-(4-methanesulphonamidophenoxy)-2-[N-methyl-N-(4-nitrophenethyl)amino]ethane

115256-11-6

dofetilide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 75 percent / Fe; HCl / ethanol / Heating
2: 92.3 percent / Et3N / CH2Cl2 / 0 °C
View Scheme
767618-90-6

N-(4-{2-[2-(4-nitro-phenyl)-ethylamino]-ethoxy}-phenyl)-methanesulfonamide

115256-11-6

dofetilide

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 87.2 percent / HCO2H / Heating
2: 75 percent / Fe; HCl / ethanol / Heating
3: 92.3 percent / Et3N / CH2Cl2 / 0 °C
View Scheme
3383-72-0

1-(2-chloroethoxy)-4-nitrobenzene

115256-11-6

dofetilide

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 64 percent / K2CO3, NaI / acetonitrile / 72 h / Heating
2: 72 percent / H2 / Raney nickel / ethanol / 16 h / 2280 Torr / Ambient temperature
3: 51 percent / CH2Cl2 / Ambient temperature
View Scheme
85176-37-0

N-methyl-N-[2-(4-nitro-phenyl)-ethyl]-amine

115256-11-6

dofetilide

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 64 percent / K2CO3, NaI / acetonitrile / 72 h / Heating
2: 72 percent / H2 / Raney nickel / ethanol / 16 h / 2280 Torr / Ambient temperature
3: 51 percent / CH2Cl2 / Ambient temperature
View Scheme
115287-37-1

1-(4-nitrophenoxy)-2-ethane

115256-11-6

dofetilide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 72 percent / H2 / Raney nickel / ethanol / 16 h / 2280 Torr / Ambient temperature
2: 51 percent / CH2Cl2 / Ambient temperature
View Scheme
115256-13-8

1-(4-aminophenoxy)-2-[N-(4-aminophenethyl)-N-methylamino]ethane

62959-51-7

N-methylsulfonyl-N′-methylimidazolium chloride

115256-11-6

dofetilide

Conditions
ConditionsYield
In 1-methyl-pyrrolidin-2-one at -12 - -5℃; for 0.833333h; Solvent; Temperature; Time; Inert atmosphere;83.1 g
115256-11-6

dofetilide

144449-71-8

Dofetilide N-oxide

Conditions
ConditionsYield
With (S,S)-(-)-3-phenyl-2-phenylsulphonyloxaziridine In dichloromethane at 20℃;
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    ProductName:dofetilide Synonyms:Dofetilidum;Xelide;N-[4-[2-[2-[4-(methanesulfonamido)phenoxy]ethyl-methylamino]ethyl]phenyl]methanesulfonamide;Dofetilide;1-MSPMPE;Dofetilida; Tikosyn; CAS:115256-11-6 Molecular Formula: C19H27N3O5S2 Molecu

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Specification

The Methanesulfonamide,N-[4-[2-[methyl[2-[4-[(methylsulfonyl)amino]phenoxy]ethyl]amino]ethyl]phenyl]- with CAS registry number of 115256-11-6 is also known as Dofetilidum. The IUPAC name is N-[4-[2-[2-[4-(Methanesulfonamido)phenoxy]ethyl-methylamino]ethyl]phenyl]methanesulfonamide. It belongs to product categories of Active Pharmaceutical Ingredients; Medicine intermediate; Antiarrhythmic; Intermediates & Fine Chemicals; Pharmaceuticals; Sulfur & Selenium Compounds. In addition, the formula is C19H27N3O5S2 and the molecular weight is 441.56. This chemical is a white crystalline solid.

Physical properties about Methanesulfonamide,N-[4-[2-[methyl[2-[4-[(methylsulfonyl)amino]phenoxy]ethyl]amino]ethyl]phenyl]- are: (1)ACD/LogP: 1.56; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -1.03; (4)ACD/LogD (pH 7.4): 0.65; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1.11; (7)ACD/KOC (pH 5.5): 1; (8)ACD/KOC (pH 7.4): 20.6; (9)#H bond acceptors: 8; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 9; (12)Polar Surface Area: 103.99Å2; (13)Index of Refraction: 1.613; (14)Molar Refractivity: 114.42 cm3; (15)Molar Volume: 328.3 cm3; (16)Polarizability: 45.36×10-24cm3; (17)Surface Tension: 57.6 dyne/cm; (18)Density: 1.344 g/cm3; (19)Flash Point: 325.2 °C; (20)Enthalpy of Vaporization: 91.13 kJ/mol; (21)Boiling Point: 614.1 °C at 760 mmHg; (22)Vapour Pressure: 5.13E-15 mmHg at 25 °C.

Preparation of Methanesulfonamide,N-[4-[2-[methyl[2-[4-[(methylsulfonyl)amino]phenoxy]ethyl]amino]ethyl]phenyl]-: it is prepared by reaction of N-methyl-4-nitrophenyl ethylamine with 2-[4-nitrophenyloxy] B bromide. The reaction needs reagents potash, sodium iodide and solvent acetonitrile. Firstly, the reaction mixture is stirred and concentrated to dryness. Secondly, the compound is dissolved in ethanol and reacts with Raney nickel. Then it is filtrated and the filtrate is concentrated to dryness. At last, the compound reacts with methanesulfonic anhydride with solvent dichloromethane. The mixture is stirred to obtained the product. 

Uses of Methanesulfonamide,N-[4-[2-[methyl[2-[4-[(methylsulfonyl)amino]phenoxy]ethyl]amino]ethyl]phenyl]-: it is used as a specific antiarrhythmic drugs, which is used to cure and prevent atrial arrhythmias, such as atrial fibrillation, atrial flutter and paroxysmal supraventricular tachycardia, and also can prevent the occurrence of ventricular tachycardia.

You can still convert the following datas into molecular structure:
1. SMILES: O=S(=O)(Nc1ccc(cc1)CCN(CCOc2ccc(cc2)NS(=O)(=O)C)C)C
2. InChI: InChI=1/C19H27N3O5S2/c1-22(13-12-16-4-6-17(7-5-16)20-28(2,23)24)14-15-27-19-10-8-18(9-11-19)21-29(3,25)26/h4-11,20-21H,12-15H2,1-3H3
3. InChIKey: IXTMWRCNAAVVAI-UHFFFAOYAP
4. Std. InChI: InChI=1S/C19H27N3O5S2/c1-22(13-12-16-4-6-17(7-5-16)20-28(2,23)24)14-15-27-19-10-8-18(9-11-19)21-29(3,25)26/h4-11,20-21H,12-15H2,1-3H3
5. Std. InChIKey: IXTMWRCNAAVVAI-UHFFFAOYSA-N