Phthalimide potassium salt → HCID 10984952, compound

HRID 1716167Notes

Reaction equation

HRID 1716167 reaction equation
CS(O[CH2:6][CH:7]([O:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH3:38])[CH2:8][O:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])(=O)=O.[C:39]1(=[O:49])[NH:43][C:42](=[O:44])[C:41]2=[CH:45][CH:46]=[CH:47][CH:48]=[C:40]12.[K]>CN(C)C=O>[CH2:25]([O:24][CH:7]([CH2:8][O:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[CH2:6][N:43]1[C:42](=[O:44])[C:41]2=[CH:45][CH:46]=[CH:47][CH:48]=[C:40]2[C:39]1=[O:49])[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH3:38]

Participants

4

Reactant 2

HCID 24194345Phthalimide potassium saltHCID 59467740HCID 59467740, compound

Product 1

HCID 10984952HCID 10984952, compoundYield 86.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

Crude O-(2,3-dimyristyloxypropyl) methanesulphonate 3 (14.2 g, 25.3 mmol) and potassium phthalimide (13.9 g, 75.0 mmol) were flushed with nitrogen and dissolved in anhydrous N,N-dimethylformamide (250 ml). The reaction was left to stir at 70° C. overnight under a constant stream of nitrogen. The N,N-dimethylformamide was removed on the rotary evaporator using a high vacuum pump instead of the usual aspirator. The residue was dissolved in chloroform (300 ml) and transferred to a separatory funnel with a chloroform rinse (50 ml), then washed with distilled water and ethanol (3×300 ml distilled water, 50 ml ethanol). The combined aqueous washes were back-extracted with chloroform (2×100 ml). The combined organic layers were dried with magnesium sulfate and the chloroform was removed on the rotary evaporator. TLC (30% ether-hexane, developed in Molybdate) indicated that the starting material had reacted to form product. This reaction yielded 13.5 g of crude N-(2,3-dimyristyloxypropyl)phthalimide 4.

Workup

  1. waitThe reaction was left
  2. customThe N,N-dimethylformamide was removed on the rotary evaporator
  3. dissolutionThe residue was dissolved in chloroform (300 ml)
  4. customtransferred to a separatory funnel with a chloroform
  5. washrinse (50 ml)
  6. washwashed with distilled water and ethanol (3×300 ml distilled water, 50 ml ethanol)
  7. extractionThe combined aqueous washes were back-extracted with chloroform (2×100 ml)
  8. dry with materialThe combined organic layers were dried with magnesium sulfate
  9. customthe chloroform was removed on the rotary evaporator
  10. customhad reacted
  11. customto form product

Sources & evidence

ORD record
ord-cf5a9d4295144975a585788bac4dcf65
Source dataset
uspto-grants-2010_09
Patent number
US07803397B2

Reaction notes

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