Hydrochloric Acid → HCID 13236101, compound

HRID 480539Notes

Reaction equation

HRID 480539 reaction equation
[CH2:1]([OH:17])[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][CH3:16].[O:18]=[P:19](Cl)(Cl)Cl.CCN(CC)CC.[CH2:30]([CH2:32][NH2:33])[OH:31].Cl.C1C[O:38]CC1>O>[CH2:1]([O:17][P:19](=[O:18])([OH:38])[O:31][CH2:30][CH2:32][NH2:33])[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][CH3:16]

Participants

8

Reactant 6

HCID 313Hydrochloric AcidHCID 700EthanolamineHCID 2682Cetyl AlcoholHCID 8028Tetrahydrofuran3×HCID 8471Triethylamine2×HCID 24813Phosphorus oxychloride

Product 1

HCID 13236101HCID 13236101, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
40 °C

Procedure

A solution of hexadecyl alcohol (26.2 g; 108 mmol) in THF (100 mL) was added dropwise in 30 min to a solution of POCl3 (16.56 g; 108 mmol) and Et3N (12.35 g; 122 mmol) in THF (200 mL) at 0° C. After 5 min a solution of ethanolamine (7.2 g; 118 mmol) and Et3N (43.51 g; 430 mmol) in THF (60 mL) was added dropwise in 60 min. at 0° C. The reaction mixture was allowed to reach room temperature in 3 h; then it was heated at 40° C. and HCl 10% (100 mL) was added. After 2 h the mixture was cooled to room temperature and addition of H2O (200 mL) afforded a precipitate that was filtered, washed with H2O and dried under reduced pressure to give the desired product (33.4 g; 91 mmol). Yield 85%. K.F.: 0.53%. The 1H-NMR, 13C-NMR, MS and IR spectra were consistent with the structure.

Workup

  1. temperatureAfter 2 h the mixture was cooled to room temperature
  2. customafforded a precipitate that
  3. filtrationwas filtered
  4. washwashed with H2O
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-b1d32f53f4de45e89d52ca770fcb8796
Source dataset
uspto-grants-2003_11
Patent number
US06652834B2

Reaction notes

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