HCID 12748355, compound → 2-(2-Phenyloxazol-5-ylmethyl)isoindole-1,3-dione

HRID 915668Notes

Reaction equation

HRID 915668 reaction equation
Br[CH2:2][C:3]1[O:7][C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[N:5][CH:4]=1.[C:14]1(=[O:24])[NH:18][C:17](=[O:19])[C:16]2=[CH:20][CH:21]=[CH:22][CH:23]=[C:15]12.[K]>CN(C)C=O>[C:8]1([C:6]2[O:7][C:3]([CH2:2][N:18]3[C:14](=[O:24])[C:15]4[C:16](=[CH:20][CH:21]=[CH:22][CH:23]=4)[C:17]3=[O:19])=[CH:4][N:5]=2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 12748355HCID 12748355, compoundHCID 24194345Phthalimide potassium salt

Product 1

HCID 691295772-(2-Phenyloxazol-5-ylmethyl)isoindole-1,3-dioneYield 99.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Dissolve 5-bromomethyl-2-phenyloxazole (1.17 g, 4.94 mmol) in dimethylformamide (15 mL) and add dropwise to a solution of potassium phthalimide (1.1 g, 5.93 mmol) in dimethylformamide (15 mL). Stir the reaction under nitrogen at room temperature overnight, concentrate to remove dimethylformamide, dissolve in ethyl acetate (75 mL), wash with saturated Na2CO3 (50 mL), and brine (75 mL). Dry the organic phase (Na2SO4), filter, and concentrate. Perform flash chromatography on silica gel eluting with 4:1 to 1:1 Hex/ethyl acetate to afford 1.5 g of 2-(2-phenyloxazol-5-ylmethyl)isoindole-1,3-dione as an off-white solid. MS: m/e=305 (MH+)

Workup

  1. customthe reaction under nitrogen at room temperature overnight
  2. concentrationconcentrate
  3. customto remove dimethylformamide
  4. dissolutiondissolve in ethyl acetate (75 mL)
  5. washwash with saturated Na2CO3 (50 mL), and brine (75 mL)
  6. dry with materialDry the organic phase (Na2SO4)
  7. filtrationfilter
  8. concentrationconcentrate

Sources & evidence

ORD record
ord-ead33618bae447eba2633c79213d5575
Source dataset
uspto-grants-2007_09
Patent number
US07265246B2

Reaction notes

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