HCID 10755030, compound → HCID 10736209, compound

HRID 1532039Notes

Reaction equation

HRID 1532039 reaction equation
Br[CH2:2][C:3]1[C:4]([O:13][CH2:14][CH3:15])=[N:5][O:6][C:7]=1[C:8]([O:10][CH2:11][CH3:12])=[O:9].[C:16]1(=[O:26])[NH:20][C:19](=[O:21])[C:18]2=[CH:22][CH:23]=[CH:24][CH:25]=[C:17]12.[K]>CN(C=O)C>[CH2:14]([O:13][C:4]1[C:3]([CH2:2][N:20]2[C:19](=[O:21])[C:18]3=[CH:22][CH:23]=[CH:24][CH:25]=[C:17]3[C:16]2=[O:26])=[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[O:6][N:5]=1)[CH3:15]

Participants

4

Reactant 2

HCID 10755030HCID 10755030, compoundHCID 24194345Phthalimide potassium salt

Product 1

HCID 10736209HCID 10736209, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
90 °C

Procedure

A solusion of ethyl 4-bromomethyl-3-ethoxyisoxazole-5-carboxylate (5 g, 17.9 mmol) in DMF (85 mL) was added to a suspension of potassium phthalimid (3.6 g, 19,7 mmol) in DMF (125 mL) at 90° C. The resulting mixture was stirred at 90° C. for 40 min, then cooled and concentrated in vacuo. Water (250 mL) was added and the aqueous phase was extracted with diethylether (2×200 mL). The organic extracts were dried (MgSO4) and concentrated in vacuo to give a crude product which was recrystallized (EtOH) to yield the title compound (3.70 g, 60%): mp 93-94° C.

Workup

  1. temperaturecooled
  2. concentrationconcentrated in vacuo
  3. additionWater (250 mL) was added
  4. extractionthe aqueous phase was extracted with diethylether (2×200 mL)
  5. dry with materialThe organic extracts were dried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. customto give a crude product which
  8. customwas recrystallized (EtOH)

Sources & evidence

ORD record
ord-2b604fe4f5eb44da989aea4a05c50954
Source dataset
uspto-grants-2001_03
Patent number
US06200999B1

Reaction notes

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