Thionyl Chloride → Chloride

HRID 2240365Notes

Reaction equation

HRID 2240365 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[C:12]([CH2:13]O)=[CH:11][CH:10]=[CH:9][N:8]=2)[CH2:3][CH2:2]1.S(Cl)([Cl:17])=O>ClCCl>[Cl-:17].[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[C:12]([CH2:13][Cl:17])=[CH:11][CH:10]=[CH:9][N:8]=2)[CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 24386Thionyl ChlorideHCID 2776571(2-Morpholino-3-Pyridinyl)Methanol

Product 2

HCID 312ChlorideHCID 61257802HCID 61257802, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (2-morpholino-3-pyridinyl)methanol (1 g, 5.01 mmol) in dichloromethane (20 ml) was added thionyl chloride (3 ml) dropwise at 0° C. and allowed to warm to room temperature. After stirring at room temperature for 6 h, solvents were removed under reduced pressure and the residue was dissolved and concentrated repeatedly in dichloromethane to remove excess of thionyl chloride. The obtained crude chloride intermediate, (2-morpholino-3-pyridinyl)methylchloride, was immediately dissolved in acetone (25 ml) and added sodium azide (1.63 g, 25.05 mmol) at room temperature. The reaction was refluxed for overnight, solvents were removed under reduced pressure, dissolved in dichloromethane (25 ml) and washed with 1M NaHCO3 (25 ml). The aqueous layer was extracted with dichloromethane (2×20 ml). The combined organic extracts were dried (Na2SO4), filtered and concentrated to yield 0.62 g (57%) of product as a thick yellowish liquid. MS (ESI+) m/z 220 (M+H)+;

Workup

  1. customsolvents were removed under reduced pressure
  2. dissolutionthe residue was dissolved
  3. concentrationconcentrated repeatedly in dichloromethane
  4. customto remove excess of thionyl chloride

Sources & evidence

ORD record
ord-3ee2cd86bfa4486d9fb4a021ae26456c
Source dataset
uspto-grants-2010_05
Patent number
US07723367B2

Reaction notes

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