PropylsulfaMide Chemical Properties

Boiling point:

249.0±23.0 °C(Predicted)

Density 

1.238±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

pka

11.06±0.60(Predicted)

form 

solid

Appearance

Colorless to off-white Solid

InChI

InChI=1S/C3H10N2O2S/c1-2-3-5-8(4,6)7/h5H,2-3H2,1H3,(H2,4,6,7)

InChIKey

FEYGBGVBTKYFOF-UHFFFAOYSA-N

SMILES

S(NCCC)(N)(=O)=O

CAS DataBase Reference

147962-41-2

PropylsulfaMide Usage And Synthesis

Uses

Propylamine sulfonamide is mainly used in pharmaceutical intermediates.

Synthesis

The general procedure for the synthesis of N-propylsulfonamide from n-propylamine and chlorosulfonyl isocyanate is as follows: first, chlorosulfonyl isocyanate (12.3 mL, 0.14 mol, 1.0 eq.) was slowly added to a solution of benzyl alcohol (14.7 mL, 0.14 mol, 1.0 eq.) in dichloromethane (DCM, 130 mL) at -35 °C over a reaction time of 30 min. . Subsequently, a solution of n-propylamine (14 mL, 0.17 mol, 1.2 eq.) and triethylamine (29.5 mL, 0.21 mol, 1.5 eq.) in DCM (35 mL) was added slowly and dropwise at -50 °C. The reaction time was 30 minutes. The reaction mixture was gradually warmed to 20 °C and kept at this temperature for 2 hours. Upon completion of the reaction, the reaction mixture was washed sequentially with water, 33% HCl and water. The mixture was then warmed up to 30 °C and the organic and aqueous layers were separated. The organic layer was washed with a mixture of triethylamine (20 mL, 0.14 mol, 1 eq.) and water (50 mL) and the pH was adjusted to be greater than 5. Next, tetrahydrofuran (THF, 85 mL) and 10% Pd/C catalyst (1 g) were added and the hydrogenation reaction was carried out for 6 hr at 25 °C under a pressure of 6 bar hydrogen. At the end of the reaction, the catalyst was removed by Celite filtration. Subsequently, the volatile solvent was removed under reduced pressure and dimethyl sulfoxide (DMSO, 120 mL) was added to dissolve the product. The resulting DMSO solution of propane-1-sulfonamide (100% theoretical yield) was used directly in the next step of the reaction.

References

[1] Patent: WO2015/4265, 2015, A1. Location in patent: Page/Page column 25; 26

PropylsulfaMide(147962-41-2)Related Product Information

• Macitidine related impurities
• CarbaMic acid, N-[(propylaMino)sulfonyl]-, phenylMethyl ester
• 5-(4-Bromophenyl)-4,6-dichloropyrimidine
• 2-(4-BROMOPHENYL)-PROPANEDIOIC ACID, 1,3-MDIETHYL ESTER
• 4(1H)-PyriMidinone, 5-(4-broMophenyl)-6-hydroxy-
• N-Propylsulfuric diamide-sodium
• SulfaMide, N-propyl-,(potassiuM salt)(1:1)
• Macitentan impurity A
• 5-Bromo-2-chloropyrimidine
• Macitentan impurity B
• macitentan
• Dichloromethane
• Macitentan IMpurity
• Masitatin impurity 1
• NA
• Masitatin impurity 3
• Macitidine impurity 2
• Macitidine impurity 5