Potassium Carbonate → HCID 698673, compound

HRID 1618225Notes

Reaction equation

HRID 1618225 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, 1H), 7.89 (d, J=7.8 Hz, 1H), 7.73 (d, J=7.8 Hz, 1H), 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-7f34096fc4104133a8061b390389e9e1
Source dataset
uspto-grants-2014_07
Patent number
US08765956B2

Reaction notes

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