Hydrochloric Acid → HCID 19372059, compound

HRID 129657Notes

Reaction equation

HRID 129657 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][CH2:14][CH2:15][CH2:16][CH2:17][C:18]([OH:20])=[O:19].[C:21]1(=[O:31])[NH:25][C:24](=[O:26])[C:23]2=[CH:27][CH:28]=[CH:29][CH:30]=[C:22]12.[K].O.Cl>CN(C)C=O>[C:21]1(=[O:31])[N:25]([CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18]([OH:20])=[O:19])[C:24](=[O:26])[C:23]2=[CH:27][CH:28]=[CH:29][CH:30]=[C:22]12

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 8313517-Bromoheptadecanoic acidHCID 24194345Phthalimide potassium salt

Product 1

HCID 19372059HCID 19372059, compoundYield 142.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

2 g of 17-bromoheptadecanoic acid are added to 2.14 g of potassium phthalimide in 40 cm3 of N,N-dimethylformamide and the mixture is heated for 6 hours at a temperature in the region of 80° C. The solution is cooled to about 20° C., it is poured into 100 cm3 of distilled water and 10 cm3 of 2N hydrochloric acid are added dropwise. The solid formed is separated by filtration. 5.13 g are obtained of a residue which is chromatographed on a column with a diameter of 4 cm containing 250 g of silica (0.020-0.045 mm) eluted with a 95/5 (by volume) mixture of methylene chloride and methanol. The first 4 fractions are discarded, the following 3 are combined and concentrated to dryness under reduced pressure (2.7 kPa) at a temperature in the region of 40° C. 3.39 g of 17-phthalimidoheptadecanoic acid are thus obtained in the form of a white solid.

Workup

  1. temperatureThe solution is cooled to about 20° C.
  2. additionare added dropwise
  3. customThe solid formed
  4. customis separated by filtration
  5. custom5.13 g are obtained of a residue which
  6. customis chromatographed on a column with a diameter of 4 cm
  7. additioncontaining 250 g of silica (0.020-0.045 mm)
  8. washeluted with a 95/5 (by volume) mixture of methylene chloride and methanol
  9. concentrationconcentrated to dryness under reduced pressure (2.7 kPa) at a temperature in the region of 40° C

Sources & evidence

ORD record
ord-92a6e1e0b44f42fabefb374f52fe41e2
Source dataset
uspto-grants-1995_11
Patent number
US05468888

Reaction notes

Loading…