Phthalimide → N-(3,5-Dimethyl-4-isoxazolylmethyl)phthalimide

HRID 1013181Notes

Reaction equation

HRID 1013181 reaction equation
Cl[CH2:2][C:3]1[C:4]([CH3:9])=[N:5][O:6][C:7]=1[CH3:8].[C:10]1(=[O:20])[NH:14][C:13](=[O:15])[C:12]2=[CH:16][CH:17]=[CH:18][CH:19]=[C:11]12.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH3:9][C:4]1[C:3]([CH2:2][N:14]2[C:10](=[O:20])[C:11]3[C:12](=[CH:16][CH:17]=[CH:18][CH:19]=3)[C:13]2=[O:15])=[C:7]([CH3:8])[O:6][N:5]=1

Participants

5

Reactant 3

HCID 6809PhthalimideHCID 11430Potassium CarbonateHCID 88246Isoxazole, 4-(chloromethyl)-3,5-dimethyl-

Product 1

HCID 135035N-(3,5-Dimethyl-4-isoxazolylmethyl)phthalimideYield 114.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-Chloromethyl-3,5-dimethyl-isoxazole (500 μL, 3.40 mmol) was added to a mixture of phthalimide (500 mg, 3.40 mmol) and K2CO3 (500 mg, 3.62 mmol) in DMF (5 mL) and stirred at ambient temperature overnight. The reaction was then heated to 70° C. for 5 hours and subsequently cooled and partitioned between ethyl acetate and water. The organic layer was washed several times with water and concentrated to give 1.0 g of the sub-title compound as a white solid. MS: ESI (positive): 257 (M+H).

Workup

  1. temperatureThe reaction was then heated to 70° C. for 5 hours
  2. temperaturesubsequently cooled
  3. custompartitioned between ethyl acetate and water
  4. washThe organic layer was washed several times with water
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-da92ac15e97643cd95a9afc15ee16560
Source dataset
uspto-grants-2011_07
Patent number
US07981912B2

Reaction notes

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