Water → N-(12-Bromododecyl)phthalimide

HRID 84990

Reaction equation

HRID 84990 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][Br:14].[C:15]1(=[O:25])[NH:19][C:18](=[O:20])[C:17]2=[CH:21][CH:22]=[CH:23][CH:24]=[C:16]12.[K].CN(C)C=O.O>ClCCl>[Br:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][N:19]1[C:15](=[O:25])[C:16]2[C:17](=[CH:21][CH:22]=[CH:23][CH:24]=2)[C:18]1=[O:20]

Participants

6

Reactant 4

HCID 962WaterHCID 6228DimethylformamideHCID 187661,12-DibromododecaneHCID 24194345Phthalimide potassium salt

Product 1

HCID 10763182N-(12-Bromododecyl)phthalimide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
160 °C

Procedure

1,12-dibromododecane (32.22 g, 98.2 mmol), potassium phthalimide (4.60 g, 24.5 mmol), and dimethylformamide (20 mL) were combined and refluxed at 160° C. for 2.5 hours. Upon cooling, water was added and the organic taken into dichloromethane (separated on a separatory funnel). The solvent was evaporated under reduced pressure and the crude product was columned in hexanes. The spots were not separated, and the fractions were combined, the solvent removed, and the crude material re-dissolved in 300 mL acetone. This was refluxed, and 10 g potassium phthalimide was added over 4 hours. The mixture was refluxed overnight. After cooling and removing the solvent, the crude product was columned using 1:1 ethyl acetate:hexanes. The top spot proved to be the desired product, which was collected as a white solid (9.30 g) that matched the reported literature: Helv. Chimica Acta. 2001, 84(3), 678-689.

Workup

  1. temperatureUpon cooling
  2. customThe solvent was evaporated under reduced pressure
  3. customThe spots were not separated
  4. customthe solvent removed
  5. dissolutionthe crude material re-dissolved in 300 mL acetone
  6. temperatureThis was refluxed
  7. addition10 g potassium phthalimide was added over 4 hours
  8. temperatureThe mixture was refluxed overnight
  9. temperatureAfter cooling
  10. customremoving the solvent
  11. customwas collected as a white solid (9.30 g) that

Sources & evidence

ORD record
ord-f48e166fc1c146a7839825ec130ed9d4
Source dataset
uspto-grants-2014_09
Patent number
US08846978B2

Linked notes

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