Hydrochloric Acid → 4-(2-Chloroethyl)thiomorpholin-4-ium 1,1-dioxide chloride
Reaction equation
[Cl-:1].O[CH2:3][CH2:4][NH+:5]1[CH2:10][CH2:9][S:8](=[O:12])(=[O:11])[CH2:7][CH2:6]1.Cl.N1C=CC=CC=1.S(Cl)([Cl:22])=O>C(Cl)(Cl)Cl.O>[Cl-:22].[Cl:1][CH2:3][CH2:4][NH+:5]1[CH2:10][CH2:9][S:8](=[O:12])(=[O:11])[CH2:7][CH2:6]1Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 25 °C
Procedure
4-(2-Hydroxyethyl)thiomorpholin-4-ium 1,1-dioxide chloride, the HCl salt of 41-1, (6.0 g, 27.82 mmol) was treated with pyridine (2.43 g, 30.60 mmol) and then warmed with a solution of thionyl chloride (4.96 g, 41.72 mmol) in chloroform (20 mL) to 60° C. After 1.5 hours the reaction was cooled to 25° C. and water was added. The chloroform was drawn off and the aqueous layer was condensed under reduced pressure to a clear syrup which crystallized upon standing. The crystals were filtered off, washed with 95% ethanol, methanol and then dried to afford 41-2. 1H-NMR (CD3OD): 4.01(t, 2H); 3.90(m, 4H); 3.71(t, 2H); 3.59(t, 4H).
Workup
- customcondensed under reduced pressure to a clear syrup which
- customcrystallized
- filtrationThe crystals were filtered off
- washwashed with 95% ethanol, methanol
- customdried
- customto afford 41-2
Sources & evidence
- ORD record
- ord-bfa3522c067548c7b65a2653efaea2a5
- Source dataset
- uspto-grants-2006_10
- Patent number
- US07115597B2
Reaction notes
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