Thionyl Chloride → HCID 86702828, compound

HRID 339774Notes

Reaction equation

HRID 339774 reaction equation
[N:1]1([CH2:7][C@H: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][C@@H: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 1268043HCID 1268043, compound

Product 1

HCID 86702828HCID 86702828, compoundYield 103%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (2S)-3-(4-morpholinyl)-1,2-propanediol (0.90 g, 5.6 mmol) in CH2Cl2 (7.5 mL) was cooled to 0° C. and added thionyl chloride (0.81 mL, 11.1 mmol, 2.0 equiv.) was added dropwise. The resulting solution was heated at the reflux temperature for 1 hr, cooled to room temperature and concentrated under reduced pressure to give 4-[(4S)-(2-oxido-1,3,2-dioxathiolan-4-yl)methyl]morpholine hydrochloride (1.40 g, 103%). This material was used in the next step without further purification.

Workup

  1. additionwas added dropwise
  2. temperatureThe resulting solution was heated at the reflux temperature for 1 hr
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-7311380053744fec9529076764c10dd8
Source dataset
uspto-grants-2014_11
Patent number
US08895549B2

Reaction notes

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