Water → HCID 21253987, compound

HRID 1531397Notes

Reaction equation

HRID 1531397 reaction equation
[CH2:1]([N:3]([CH2:13][CH3:14])[C:4]1[CH:5]=[C:6]([OH:12])[C:7](=[CH:10][CH:11]=1)[CH:8]=[O:9])[CH3:2].[OH-].[Na+].[C:17](Cl)(=[O:22])[C:18]([CH3:21])([CH3:20])[CH3:19].O>O1CCOCC1.S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC>[CH2:13]([N:3]([CH2:1][CH3:2])[C:4]1[CH:11]=[CH:10][C:7]([CH:8]=[O:9])=[C:6]([O:12][C:17](=[O:22])[C:18]([CH3:21])([CH3:20])[CH3:19])[CH:5]=1)[CH3:14]

Participants

7

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 62493Pivaloyl chlorideHCID 872934-(Diethylamino)-2-hydroxybenzaldehyde

Product 1

HCID 21253987HCID 21253987, compoundYield 89.5%

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 312751,4-DioxaneSolvent2×

Procedure

In 25 ml of 1,4-dioxane, 1.93 g of 4-diethylaminosalicylaldehyde was dissolved. To the resulting solution, 1.08 g of powdery sodium hydroxide and 12 mg of tetrabutylammonium hydrogensulfate were added, followed by stirring at room temperature. To the resulting heterogeneous solution, a solution of 1.45 g of pivaloyl chloride dissolved in 10 ml of 1,4-dioxane was added over 20 minutes and the mixture was stirred for 1 hour as was. To the reaction mixture, 20 ml of water was added and the mixture was extracted with ethyl acetate. The organic phase was dried over magnesium sulfate and the solvent was distilled off, whereby 2.48 g of the title compound was obtained in the form of a brown oil (yield: 89%).

Workup

  1. additionwas added over 20 minutes
  2. stirringthe mixture was stirred for 1 hour
  3. extractionthe mixture was extracted with ethyl acetate
  4. dry with materialThe organic phase was dried over magnesium sulfate
  5. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-3b0a500bab6947f6ad23b6cbbf0c1247
Source dataset
uspto-grants-2001_03
Patent number
US06197968B1

Reaction notes

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