Sodium Carbonate → HCID 14457930, compound

HRID 357540Notes

Reaction equation

HRID 357540 reaction equation
[CH2:1]([O:8][CH2:9][CH2:10][O:11][C:12]1[CH:17]=[CH:16][N:15]=[C:14]([CH2:18]O)[C:13]=1[CH3:20])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(Cl)([Cl:23])=O.C(=O)([O-])[O-].[Na+].[Na+]>C(Cl)(Cl)Cl>[CH2:1]([O:8][CH2:9][CH2:10][O:11][C:12]1[CH:17]=[CH:16][N:15]=[C:14]([CH2:18][Cl:23])[C:13]=1[CH3:20])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 24386Thionyl ChlorideHCID 14457929HCID 14457929, compound

Product 1

HCID 14457930HCID 14457930, compoundYield 111.4%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

5.3 g of 4-(2-benzyloxyethoxy)-2-hydroxymethyl-3-methylpyridine was dissolved in 60 ml of chloroform to obtain a solution. A solution of 5.8 g of thionyl chloride in 40 ml of chloroform was dropwise added to the above solution under cooling with ice. The obtained mixture was stirred at a room temperature for 7 hours and distilled under a reduced pressure to obtain a residue. 200 ml of a 2N aqueous solution of sodium carbonate was added to the residue. The obtained mixture was extracted with chloroform and the extract was dried over magnesium sulfate and distilled to remove the chloroform. 6.3 g of the title compound was obtained.

Workup

  1. customto obtain a solution
  2. temperatureunder cooling with ice
  3. distillationdistilled under a reduced pressure
  4. customto obtain a residue
  5. extractionThe obtained mixture was extracted with chloroform
  6. dry with materialthe extract was dried over magnesium sulfate
  7. distillationdistilled
  8. customto remove the chloroform

Sources & evidence

ORD record
ord-77ca57962d8c494591cd53675a9ac078
Source dataset
uspto-grants-1998_11
Patent number
US05840910

Reaction notes

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