HCID 18958347, compound → HCID 15232941, compound

HRID 2379288Notes

Reaction equation

HRID 2379288 reaction equation
[C:1]1(=[O:11])[NH:5][C:4](=[O:6])[C:3]2=[CH:7][CH:8]=[CH:9][CH:10]=[C:2]12.[K].S(O[CH2:24][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][CH2:38][CH2:39][CH2:40][C:41]([O:43][CH3:44])=[O:42])(C1C=CC(C)=CC=1)(=O)=O>CN(C)C=O>[C:1]1(=[O:11])[N:5]([CH2:24][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][CH2:38][CH2:39][CH2:40][C:41]([O:43][CH3:44])=[O:42])[C:4](=[O:6])[C:3]2=[CH:7][CH:8]=[CH:9][CH:10]=[C:2]12

Participants

4

Reactant 2

HCID 18958347HCID 18958347, compoundHCID 24194345Phthalimide potassium salt

Product 1

HCID 15232941HCID 15232941, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
110 °C

Procedure

A mixture of potassium phthalimide (2.96 g, 16.0 mmoles) and 100 ml of dried N,N-dimethylformamide was heated at 110° C. To this mixture was added dropwise 80 ml of a solution of methyl 18-tosyloxyoctadecanoate (5.0 g, 10.7 mmoles) in 80 ml of N,N-dimethylformamide, and the mixture was heated with stirring at 110° C. for 2 hours. The reaction mixture was poured into ice water to a total volume of 1.2 1, and stirred for 30 minutes. Thereafter, the precipitates that formed were collected by filtration and dissolved in chloroform. The obtained solution was washed with water and then with saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and isolated and purified by silica gel column chromatography [eluent: mixture of benzene and methylene chloride (volume ratio: 2:1)], to give methyl 18-phtahlimideocatadecanoate (4.15 g, 88%) having the following properties.

Workup

  1. temperaturethe mixture was heated
  2. stirringstirred for 30 minutes
  3. customThereafter, the precipitates
  4. customthat formed
  5. filtrationwere collected by filtration
  6. dissolutiondissolved in chloroform
  7. washThe obtained solution was washed with water
  8. dry with materialwith saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate
  9. customisolated
  10. custompurified by silica gel column chromatography [eluent: mixture of benzene and methylene chloride (volume ratio: 2:1)]
  11. customto give methyl 18-phtahlimideocatadecanoate (4.15 g, 88%)

Sources & evidence

ORD record
ord-0fbb07c7b3be47d8b51477ed78001059
Source dataset
uspto-grants-1994_11
Patent number
US05360914

Reaction notes

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