Sodium Carbonate → HCID 14457930, compound

HRID 609826Notes

Reaction equation

HRID 609826 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-35d56fa3a60844259328062c3faab85f
Source dataset
uspto-grants-1999_12
Patent number
US05998445

Reaction notes

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