THIOMORPHOLINE 1,1-DIOXIDE HYDROCHLORIDE Chemical Properties

Melting point:

307 °C (decomp)

storage temp. 

Inert atmosphere,Room Temperature

form 

solid

color 

White

InChI

InChI=1S/C4H9NO2S.ClH/c6-8(7)3-1-5-2-4-8;/h5H,1-4H2;1H

InChIKey

UOMTVKMKHZMFMQ-UHFFFAOYSA-N

SMILES

C1S(=O)(=O)CCNC1.[H]Cl

Safety Information

HazardClass 

IRRITANT

HS Code 

29349990

THIOMORPHOLINE 1,1-DIOXIDE HYDROCHLORIDE Usage And Synthesis

Uses

Thiomorpholine 1,1-dioxide hydrochloride is used as a pharmaceutical intermediate.

Chemical Properties

white to light yellow solid

Synthesis

The general procedure for the synthesis of thiomorpholine-1,1-dioxide hydrochloride from tert-butyl thiomorpholine-4-carboxylate 1,1-dioxide was as follows: tert-butyl 1,1-dioxothiomorpholine-4-carboxylate (2.03 g, 8.63 mmol) was dissolved in a hydrochloric acid-methanol (10%, 20 mL, purchased from Tokyo Kasei Kogyo Co.) and tetrahydrofuran (20 mL) in a solvent mixture. Concentrated hydrochloric acid (4.0 mL) was slowly added to the reaction system under stirring at room temperature. The reaction mixture was continued to be stirred at room temperature for 3 hours. Upon completion of the reaction, the solvent was removed by concentration under reduced pressure. Methanol (20 mL), tetrahydrofuran (20 mL), and concentrated hydrochloric acid (4.0 mL) were added to the resulting solid, followed by the addition of water (10 mL) to ensure complete dissolution of the solid. This solution was stirred at room temperature for 1 hour. The solvent was again concentrated under reduced pressure to remove the solvent. The resulting crystals were suspended in methanol, filtered, washed with methanol and dried under ventilated conditions to give thiomorpholine-1,1-dioxide hydrochloride as colorless crystals (1.49 g, 8.65 mmol, quantitative yield). The product was characterized by 1H-NMR (DMSO-d6): δ 3.54 (8H, m), 9.83 (2H, brs).

References

[1] Patent: EP1522540, 2005, A1. Location in patent: Page/Page column 70
[2] Journal of Medicinal Chemistry, 2016, vol. 59, # 20, p. 9541 - 9559

THIOMORPHOLINE 1,1-DIOXIDE HYDROCHLORIDE(59801-62-6)Related Product Information

• Thiomorpholine-1,1-dioxide
• thiomorpholin-3-one
• ThioMorpholine-1-oxide HCl
• Furfuryl thiopropionate
• Ethanethioic acid S-ethyl ester
• Furfuryl thioformate
• Methyl 2-thiofuroate
• S-N-PROPYL THIOACETATE
• S-ETHYL THIOPROPIONATE
• Thiobenzoic acid
• Furfuryl thioacetate
• Ethyl thiooxamate
• THIOMORPHOLINE-3-CARBOXYLIC ACID ETHYL ESTER HYDROCHLORIDE
• Moroxydine
• Morpholine
• 4,4'-Dithiodimorpholine
• Thiomorpholine
• THIOMORPHOLINE HYDROCHLORIDE