Octadecyl isocyanate → N-(2-Isopropyl-1,3-oxazolidin-3-yl)-ethoxycarbonyl stearylamine

HRID 1414694Notes

Reaction equation

HRID 1414694 reaction equation
C(N=[C:18]=[O:19])CCCCCCCCCCCCCCC.[CH2:20]([N:38]=[C:39]=[O:40])[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][CH2:35][CH2:36][CH3:37].[CH:41]([CH:44]1[N:48](CCO)[CH2:47][CH2:46][O:45]1)([CH3:43])[CH3:42].[N-]=[C:53]=O>>[CH:41]([CH:44]1[N:48]([N:38]([C:39]([O:19][CH2:18][CH3:53])=[O:40])[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][CH2:35][CH2:36][CH3:37])[CH2:47][CH2:46][O:45]1)([CH3:43])[CH3:42]

Participants

5

Reactant 4

HCID 66988Octadecyl isocyanateHCID 74751Hexadecane, 1-isocyanato-HCID 105034IsocyanateHCID 1200432-Isopropyl-1,3-oxazolidine-3-ethanol

Product 1

HCID 18691695N-(2-Isopropyl-1,3-oxazolidin-3-yl)-ethoxycarbonyl stearylamine

Procedure

295 g of a mixture of hexadecylisocyanate and octadecylisocyanate (commercial stearylisocyanate, 14.8% NCO) are slowly added to 159 g (1 mol) of 2-(2-isopropyl-1,3-oxazolidin-3-yl)-ethanol and 0.1 g of Sn(II) octoate at room temperature with stirring. Stirring is continued for 5 hours at about 50° C after all the isocyanate has been added. The product solidifies after some time to a waxy mass which melts to a clear liquid at temperatures of from 65° to 70° C.

Workup

  1. stirringStirring
  2. custommelts to a clear liquid at temperatures of from 65° to 70° C.

Sources & evidence

ORD record
ord-5d63ddedfba2424292a0e51d48c289f4
Source dataset
uspto-grants-1977_01
Patent number
US04002601

Reaction notes

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