Octadecyl isocyanate → HCID 54548106, compound

HRID 728487Notes

Reaction equation

HRID 728487 reaction equation
[C:1]([O:9][CH2:10][CH:11]([CH2:14][CH:15]([O:17][C:18](=[O:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[CH3:16])[CH2:12][OH:13])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:26]([N:44]=[C:45]=[O:46])[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][CH2:41][CH2:42][CH3:43]>N1C=CC=CC=1>[C:1]([O:9][CH2:10][CH:11]([CH2:14][CH:15]([O:17][C:18](=[O:25])[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)[CH3:16])[CH2:12][O:13][C:45](=[O:46])[NH:44][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][CH2:41][CH2:42][CH3:43])(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 66988Octadecyl isocyanateHCID 54105575HCID 54105575, compound

Product 1

HCID 54548106HCID 54548106, compoundYield 91.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 3.70 g (11.2 mM) of 2-(2-benzoyloxypropan-1-yl)-3-hydroxypropyl benzoate m5 and 4.964 g (16.8 mM) of octadecyl isocyanate in 74 ml of pyridine is heated at 70° C. for 15 hours and the solvent is evaporated. To the residue with cooling, is added 2N aqueous hydrochloric acid and the product is isolated by ethyl acetate extraction. The ethyl acetate layer is washed with saturated aqueous sodium bicarbonate and saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate and evaporated. Purification of the product by column silica gel chromatography using n-hexane-ethyl acetate (1:1) as an eluent gives 6.28 g (87.8% yield) of the titled compound m6.

Workup

  1. customthe solvent is evaporated
  2. temperatureTo the residue with cooling
  3. additionis added 2N aqueous hydrochloric acid
  4. customthe product is isolated by ethyl acetate extraction
  5. washThe ethyl acetate layer is washed with saturated aqueous sodium bicarbonate and saturated aqueous sodium chloride
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customevaporated
  8. customPurification of the product by column silica gel chromatography

Sources & evidence

ORD record
ord-978d86755e194762acdfcd64f0872e5a
Source dataset
uspto-grants-1991_09
Patent number
US05047540

Reaction notes

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