Phthalimide potassium salt → 2-((2-Methylthiazol-5-yl)methyl)isoindoline-1,3-dione

HRID 915661Notes

Reaction equation

HRID 915661 reaction equation
Br[CH2:2][C:3]1[S:7][C:6]([CH3:8])=[N:5][CH:4]=1.[C:9]1(=[O:19])[NH:13][C:12](=[O:14])[C:11]2=[CH:15][CH:16]=[CH:17][CH:18]=[C:10]12.[K]>CN(C)C=O>[CH3:8][C:6]1[S:7][C:3]([CH2:2][N:13]2[C:9](=[O:19])[C:10]3[C:11](=[CH:15][CH:16]=[CH:17][CH:18]=3)[C:12]2=[O:14])=[CH:4][N:5]=1

Participants

4

Reactant 2

HCID 24194345Phthalimide potassium saltHCID 552507865-(Bromomethyl)-2-methyl-1,3-thiazole

Product 1

HCID 469423262-((2-Methylthiazol-5-yl)methyl)isoindoline-1,3-dioneYield 40.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Add 5-bromomethyl-2-methylthiazole (390 mg, 2.03 mmol) in dimethylformamide (2 mL) dropwise to a suspension of potassium phthalimide (434 mg, 2.34 mmol) in dimethylformamide (8 mL). Stir the reaction under nitrogen at room temperature overnight. Concentrate the mixture in vacuo, dissolve in ethyl acetate (100 mL), and wash with water (100 mL). Dry the organic phase (sodium sulfate), filter, and concentrate. Perform flash chromatography on silica gel, eluting first with 4:1 hexane/ethyl acetate, then 100% ethyl acetate to afford 210 mg of 2-(2-methylthiazol-5-ylmethyl)isoindole-1,3-dione as a tan solid. MS: m/z=259 (MH+).

Workup

  1. customthe reaction under nitrogen at room temperature overnight
  2. concentrationConcentrate the mixture in vacuo
  3. dissolutiondissolve in ethyl acetate (100 mL)
  4. washwash with water (100 mL)
  5. dry with materialDry the organic phase (sodium sulfate)
  6. filtrationfilter
  7. concentrationconcentrate
  8. washPerform flash chromatography on silica gel, eluting first with 4:1 hexane/ethyl acetate

Sources & evidence

ORD record
ord-a9fccd586ac842e3baf56f4f8bd03b71
Source dataset
uspto-grants-2007_09
Patent number
US07265246B2

Reaction notes

Loading…