Phthalimide potassium salt → HCID 69130030, compound

HRID 915686Notes

Reaction equation

HRID 915686 reaction equation
[C:1]1(=[O:11])[NH:5][C:4](=[O:6])[C:3]2=[CH:7][CH:8]=[CH:9][CH:10]=[C:2]12.[K].Br[CH2:14][C:15]1[N:16]=[CH:17][S:18][C:19]=1[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>CN(C)C=O>[C:20]1([C:19]2[S:18][CH:17]=[N:16][C:15]=2[CH2:14][N:5]2[C:1](=[O:11])[C:2]3[C:3](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:4]2=[O:6])[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

4

Reactant 2

HCID 24194345Phthalimide potassium saltHCID 69129919HCID 69129919, compound

Product 1

HCID 69130030HCID 69130030, compoundYield 52.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Prepare a cold (0° C.) solution of potassium phthalimide (350 mg, 1.8 mmol) in dimethylformamide (25 mL). Add dropwise 4-bromomethyl-5-phenyl-thiazole (400 mg, 1.6 mmol) in dimethylformamide (10 mL). Warm the reaction to room temperature, stir for 3 hours and then concentrate. Dissolve the residue in ethyl acetate (100 mL), wash with saturated Na2CO3 (50 mL) and brine (50 mL), then dry (Na2SO4), filter and concentrate to a brown residue. Chromatograph (silica gel, 4:1 hexane/ethyl acetate) to afford 2-(5-phenylthiazol-4-ylmethyl)isoindole-1,3-dione (270 mg).

Workup

  1. temperatureWarm
  2. customthe reaction to room temperature
  3. concentrationconcentrate
  4. dissolutionDissolve the residue in ethyl acetate (100 mL)
  5. washwash with saturated Na2CO3 (50 mL) and brine (50 mL)
  6. dry with materialdry (Na2SO4)
  7. filtrationfilter
  8. concentrationconcentrate to a brown residue

Sources & evidence

ORD record
ord-11efecdce03c48e5a9faf7c43a5f801b
Source dataset
uspto-grants-2007_09
Patent number
US07265246B2

Reaction notes

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