Phthalimide → HCID 21489533, compound

HRID 1974372Notes

Reaction equation

HRID 1974372 reaction equation
[H-].[Na+].[C:3]1(=[O:13])[NH:7][C:6](=[O:8])[C:5]2=[CH:9][CH:10]=[CH:11][CH:12]=[C:4]12.Br[CH2:15][C:16]1[CH:21]=[CH:20][C:19]([C:22](=[O:27])[C:23]([CH3:26])([CH3:25])[CH3:24])=[CH:18][CH:17]=1>CC(N(C)C)=O>[C:3]1(=[O:13])[N:7]([CH2:15][C:16]2[CH:21]=[CH:20][C:19]([C:22](=[O:27])[C:23]([CH3:25])([CH3:24])[CH3:26])=[CH:18][CH:17]=2)[C:6](=[O:8])[C:5]2=[CH:9][CH:10]=[CH:11][CH:12]=[C:4]12

Participants

5

Reactant 3

HCID 6809PhthalimideHCID 24758Sodium hydrideHCID 128310071-[4-(Bromomethyl)phenyl]-2,2-dimethylpropan-1-one

Product 1

HCID 21489533HCID 21489533, compound

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent3×

Procedure

A suspension of 22.4 g. (0.447 mole) of sodium hydride (50% in mineral oil) in 200 ml. dimethylacetamide is treated dropwise by the addition of 59.6 g. (0.406 mole) phthalimide in 500 ml. dimethylacetamide. The mixture is stirred for 2 more hours at room temperature and then treated dropwise with 100 g. (0.406 mole) α-bromo-p-pivaloyl toluene in 300 ml. dimethylacetamide. The resulting mixture is stirred at room temperature for 18 hours and then the solvent is removed in vacuo. The residue is taken up in methylene chloride/water and the layers separated. The water layer is washed twice with methylene chloride and the combined methylene chloride layers washed twice with water, dried over anhydrous magnesium sulfate, filtered and evaporated. The resulting solid is triturated with ether to give 4'-(phthalimidomethyl)pivalophenone; m.p. 138°-140.5° C.

Workup

  1. additionA suspension of 22.4 g
  2. additiontreated dropwise with 100 g
  3. stirringThe resulting mixture is stirred at room temperature for 18 hours
  4. customthe solvent is removed in vacuo
  5. customthe layers separated
  6. washThe water layer is washed twice with methylene chloride
  7. washthe combined methylene chloride layers washed twice with water
  8. dry with materialdried over anhydrous magnesium sulfate
  9. filtrationfiltered
  10. customevaporated
  11. customThe resulting solid is triturated with ether

Sources & evidence

ORD record
ord-ff6785c85b174435ac7fefe281fc4b36
Source dataset
uspto-grants-1976_12
Patent number
US04000307

Reaction notes

Loading…