Potassium Carbonate → HCID 698673, compound

HRID 1406168Notes

Reaction equation

HRID 1406168 reaction equation
[Br:1][C:2]1[CH:12]=[CH:11][CH:10]=[C:4]2[C:5]([NH:7]C(=O)[C:3]=12)=[O:6].Br[CH2:14][CH2:15][O:16][C:17](=[O:19])[CH3:18].[C:20](=[O:23])([O-])[O-].[K+].[K+]>CC(C)=O>[CH2:15]([O:16][C:17](=[O:19])[CH2:18][N:7]1[C:5](=[O:6])[C:4]2[C:10](=[CH:11][CH:12]=[C:2]([Br:1])[CH:3]=2)[C:20]1=[O:23])[CH3:14]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 135641-Acetoxy-2-bromoethaneHCID 226073074-Bromo-1H-isoindole-1,3(2H)-dione

Product 1

HCID 698673HCID 698673, compoundYield 99.4%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Bromophthalimide (35 g, 155 mmol) and bromoethylacetate (31 g, 186 mmol) were dissolved in 700 ml of acetone. Potassium carbonate (64.2 g, 465 mmol) was added and resulting suspension was stirred at reflux for 18 h. After cooling, the mixture was filtered. Filtrate was evaporated to give 48.12 g (154 mmol) of solid product. 1H NMR (200 MHz, CDCl3) δ 8.00 (s, 1 H), 7.89 (d, J=7.8 Hz, 1 H), 7.73 (d, J=7.8 Hz, 1 H), 4.41 (s, 2 H), 4.21 (q, J=7.0 Hz, 2 H), 1.28 (t, J=7.0 Hz, 3 H).

Workup

  1. customresulting suspension
  2. temperatureat reflux for 18 h
  3. temperatureAfter cooling
  4. filtrationthe mixture was filtered
  5. customFiltrate was evaporated

Sources & evidence

ORD record
ord-85deeb8bfc8542f2bbff1001a0cc070c
Source dataset
uspto-grants-2014_12
Patent number
US08916585B2

Reaction notes

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