Thionyl Chloride → HCID 22380609, compound

HRID 895644Notes

Reaction equation

HRID 895644 reaction equation
[CH:1]([O:3][CH2:4][C:5]1[CH:18]=[CH:17][C:8]([C:9]([NH:11][C:12]([CH3:16])([CH3:15])[CH2:13][OH:14])=O)=[CH:7][CH:6]=1)=[O:2].S(Cl)(Cl)=O>>[CH3:15][C:12]1([CH3:16])[CH2:13][O:14][C:9]([C:8]2[CH:17]=[CH:18][C:5]([CH2:4][O:3][CH:1]=[O:2])=[CH:6][CH:7]=2)=[N:11]1

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 22380769HCID 22380769, compound

Product 1

HCID 22380609HCID 22380609, compoundYield 63%

Procedure

4-(Formyloxymethyl)-N-(1,1-dimethyl-2-hydroxyethyl)benzamide (64 mg) was added with thionyl chloride (56 μl) and stirred at room temperature for 30 minutes. The solvent was evaporated under reduced pressure, and then the residue was added with water (5 ml) and extracted twice with ethyl acetate (5 ml). The organic layer was dried over anhydrous magnesium sulfate, and then the solvent was evaporated under reduced pressure. The residue was purified by preparative thin layer silica gel column chromatography (developing solvent: hexane:ethyl acetate=2:1) to obtain 37.4 mg of the title compound. Yield: 63%.

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. additionthe residue was added with water (5 ml)
  3. extractionextracted twice with ethyl acetate (5 ml)
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue was purified by preparative thin layer silica gel column chromatography (developing solvent: hexane:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-6cbd92cd3397440bb1f051102dbc5ba8
Source dataset
uspto-grants-2005_07
Patent number
US06916822B2

Reaction notes

Loading…