Thionyl Chloride → HCID 57500338, compound

HRID 2273523Notes

Reaction equation

HRID 2273523 reaction equation
S(Cl)([Cl:3])=O.[CH2:5]([O:12][C:13]1[C:14]([CH2:19]O)=[N:15][CH:16]=[CH:17][CH:18]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.C(=O)(O)[O-].[Na+]>ClCCl.O>[CH2:5]([O:12][C:13]1[C:14]([CH2:19][Cl:3])=[N:15][CH:16]=[CH:17][CH:18]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

6

Reactant 3

HCID 24386Thionyl ChlorideHCID 516892Sodium BicarbonateHCID 13217540(3-(Benzyloxy)pyridin-2-yl)methanol

Product 1

HCID 57500338HCID 57500338, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

25.2 ml of thionyl chloride are added to the solution of 40 g (0.19 mol) of 3-(benzyloxy)-2-(hydroxymethyl)pyridine (CAS 6059-29-6; Desideri, N; Sestili, I; Manarini, S; Cerletti, C; Stein; Eur. J. Med. Chem. Chim. Ther.; 26 (4) 1991; 455-460) in 265 ml of dichloromethane. The solution is stirred at ambient temperature under nitrogen, and then concentrated to dryness. The residue obtained is dissolved in water. Sodium bicarbonate is added until a solution at neutral pH is obtained. The aqueous solution is extracted with ethyl acetate. The organic phase is washed with a saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulphate, and then concentrated to dryness. 41 g (95%) of a brown oil are obtained.

Workup

  1. concentrationconcentrated to dryness
  2. customThe residue obtained
  3. customis obtained
  4. extractionThe aqueous solution is extracted with ethyl acetate
  5. washThe organic phase is washed with a saturated aqueous solution of sodium chloride
  6. dry with materialdried over anhydrous sodium sulphate
  7. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-a02e95c53b3446549ef0772dfc1c944f
Source dataset
uspto-grants-2015_09
Patent number
US09120819B2

Reaction notes

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