Thionyl Chloride → 4-[(2-Oxido-1,3,2-dioxathiolan-4-yl)methyl]morpholine hydrochloride

HRID 339757Notes

Reaction equation

HRID 339757 reaction equation
[N:1]1([CH2:7][CH:8]([OH:11])[CH2:9][OH:10])[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[S:12](Cl)([Cl:14])=[O:13]>C(Cl)Cl>[ClH:14].[O:13]=[S:12]1[O:11][CH:8]([CH2:7][N:1]2[CH2:6][CH2:5][O:4][CH2:3][CH2:2]2)[CH2:9][O:10]1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 1108503-Morpholinopropane-1,2-diol

Product 1

HCID 866524324-[(2-Oxido-1,3,2-dioxathiolan-4-yl)methyl]morpholine hydrochlorideYield 113.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

3-Morpholin-4-ylpropane-1,2-diol (2.1 g, 9.07 mmol) was dissolved in DCM (15 mL) and cooled to 0° C. The cooled solution was treated with thionyl chloride (1.81 mL, 24.8 mmol) and then heated at the reflux temperature for 1 h. The reaction mixture was then concentrated under reduced pressure to give a solid (2.5 g, 97%): 1H NMR (DMSO-d6) δ: 11.4 (1H, br s), 5.64-5.55 (1H, m) 4.82 (1H, dd), 4.50 (1H, dd), 4.02-3.71 (4H, m), 3.55-3.33 (4H, m), 3.26-3.06 (2H, br s).

Workup

  1. temperatureheated at the reflux temperature for 1 h
  2. concentrationThe reaction mixture was then concentrated under reduced pressure

Sources & evidence

ORD record
ord-0922c837f9414467b8e51e61a03467f4
Source dataset
uspto-grants-2014_11
Patent number
US08895549B2

Reaction notes

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