Sodium Iodide → HCID 19389138, compound

HRID 1757799Notes

Reaction equation

HRID 1757799 reaction equation
C(C1C=CC(NC2C=CC=CC=2)=CC=1)CCCCCCCCCCCCC.Br[CH2:29][C:30]([O:32]C)=[O:31].C(=O)([O-])[O-].[K+].[K+].[I-].[Na+].[CH2:42]([C:56]1[CH:61]=[CH:60][C:59]([NH:62][CH2:63][C:64]([OH:66])=[O:65])=[CH:58][CH:57]=1)[CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH3:55]>CN(C=O)C>[C:64]([CH2:63][N:62]([C:59]1[CH:60]=[CH:61][C:56]([CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH3:55])=[CH:57][CH:58]=1)[CH2:29][C:30]([OH:32])=[O:31])([OH:66])=[O:65]

Participants

7

Reactant 5

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 10883045HCID 10883045, compoundHCID 86748950HCID 86748950, compound

Product 1

HCID 19389138HCID 19389138, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 1.0 g (3.45 mmol) of 4-tetradecylphenyl aniline (Aldrich Chemical Company), 5.0 ml (0.052 mol) of methyl bromoacetate, 0.95 g (6.9 mmol) of potassium carbonate and 0.5 g (3.45 mmol) of sodium iodide in 15 ml of DMF was stirred and heated at 100° for 45 hours. The solvent was removed at reduced pressure and water was added to the residue. The product was extracted with ethyl acetate and the extract was washed with sodium bisulfite solution, dried and concentrated. The residue was purified by chromatography on silica gel using 25% ethyl acetate-hexane togive 0.7 g of N-(2-methoxy-2-oxoethyl)-N-(4-tetradecylphenyl)glycine methylester. This dimethyl ester was hydrolyzed by treatment with 1.5 ml of 6N NaOH in 50 ml of methanol. The mixture was warmed briefly to dissolve the ester and then was kept at room temperature for 3 days. The solvent was removed at reduced pressure and the residue was acidified to pH 2. The product was extracted with ethyl acetate and the dried extract was concentrated at reduced pressure to a solid which was recrystallized from methanol-water to give 0.26 g, mp 160°-165°, of N-carboxymethyl)-N-(4-tetradecylphenyl)glycine.

Workup

  1. temperatureheated at 100° for 45 hours
  2. customThe solvent was removed at reduced pressure and water
  3. additionwas added to the residue
  4. extractionThe product was extracted with ethyl acetate
  5. washthe extract was washed with sodium bisulfite solution
  6. customdried
  7. concentrationconcentrated
  8. customThe residue was purified by chromatography on silica gel using 25% ethyl acetate-hexane togive 0.7 g of N-(2-methoxy-2-oxoethyl)-N-(4-tetradecylphenyl)glycine methylester
  9. temperatureThe mixture was warmed briefly
  10. dissolutionto dissolve the ester
  11. customThe solvent was removed at reduced pressure
  12. extractionThe product was extracted with ethyl acetate
  13. extractionthe dried extract
  14. concentrationwas concentrated at reduced pressure to a solid which
  15. customwas recrystallized from methanol-water
  16. customto give 0.26 g, mp 160°-165°

Sources & evidence

ORD record
ord-14a64b69c40343e882dbfe911ed57f91
Source dataset
uspto-grants-1995_08
Patent number
US05446189

Reaction notes

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