Octadecyl isocyanate → HCID 19884244, compound

HRID 846971Notes

Reaction equation

HRID 846971 reaction equation
[C:1]([S:4][CH2:5][CH:6]([O:16][CH3:17])[CH2:7][O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)(=[O:3])C.[CH2:18]([N:36]=C=O)[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35]>N1C=CC=CC=1>[CH2:9]([O:8][CH2:7][CH:6]([O:16][CH3:17])[CH2:5][S:4][C:1](=[O:3])[NH:36][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 66988Octadecyl isocyanateHCID 198241381-Acetylthio-3-benzyloxy-2-methoxypropane

Product 1

HCID 19884244HCID 19884244, compoundYield 117.5%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 7.258 g (34.2 mM) of 3-benzyloxy-2-methoxypropylthioalcohol VII 6 and 11.65 g (39.4 mM) of octadecylisocyanate in 100 ml of pyridine is heated under reflux for 1 hour. The reaction mixture is concentrated and the residue is purified by column chromatography on silica gel using a toluene-ethyl acetate (9:1 to 4:1) mixture as an eluent to give 17.027 g (33.6 mM) of the titled compound, 3-benzyloxy-2-methoxy-1-octadecylcarbamoylthiopropane VI 6 as a solid in 98% yield.

Workup

  1. temperatureunder reflux for 1 hour
  2. concentrationThe reaction mixture is concentrated
  3. customthe residue is purified by column chromatography on silica gel using a toluene-ethyl acetate (9:1 to 4:1) mixture as an eluent

Sources & evidence

ORD record
ord-4797e7ef886b43bcbfedc21583ef4cd4
Source dataset
uspto-grants-1992_08
Patent number
US05138067

Reaction notes

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