Ethylene Glycol → 2-hydroxyethyl N-octadecylcarbamate

HRID 1285241Notes

Reaction equation

HRID 1285241 reaction equation
[CH2:1]([N:19]=[C:20]=[O:21])[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][CH3:18].[CH2:22]([OH:25])[CH2:23][OH:24]>N1C=CC=CC=1>[CH2:1]([NH:19][C:20]([O:24][CH2:23][CH2:22][OH:25])=[O:21])[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][CH3:18]

Participants

4

Reactant 2

HCID 174Ethylene GlycolHCID 66988Octadecyl isocyanate

Product 1

HCID 2392012-hydroxyethyl N-octadecylcarbamateYield 79.7%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

In 50 ml of pyridine are dissolved 11.8 g (40 mM) of stearyl isocyanate and 12.4 g (200 mM) of ethylene glycol, and the solution is allowed to stand at room temperature overnight. The reaction mixture is concentrated to dryness under reduced pressure, and the residue is recrystallized from 100 ml of methanol to give 11.38 g (yield 79.5%) of the contemplated product. mp. 81°-82° C.

Workup

  1. concentrationThe reaction mixture is concentrated to dryness under reduced pressure
  2. customthe residue is recrystallized from 100 ml of methanol

Sources & evidence

ORD record
ord-39e1833a7f294420b71a2fb09146ab99
Source dataset
uspto-grants-1986_01
Patent number
US04565865

Reaction notes

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