tert-Butanol → N,N-diethyl-N'-n-undecyl urea

HRID 67789Notes

Reaction equation

HRID 67789 reaction equation
[OH-].[Na+].[CH2:3]([NH:5][CH2:6][CH3:7])[CH3:4].Cl[NH:9][C:10](=O)[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20]C.[C:23]([OH:27])(C)(C)C>O.CC(C)=O>[CH2:3]([N:5]([CH2:6][CH3:7])[C:23]([NH:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])=[O:27])[CH3:4]

Participants

7

Reactant 4

HCID 6386tert-ButanolHCID 8021DiethylamineHCID 14798Sodium HydroxideHCID 19040106lauric N-chloramide

Product 1

HCID 20527941N,N-diethyl-N'-n-undecyl ureaYield 90%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Conditions

Temperature
40 °C

Procedure

4 g. (0.1 mol) of sodium hydroxide, dissolved in 10 ml of water, and 7.3 g. (0.1 mol) of diethylamine were simultaneously added to a solution containing 23.35 g. (0.1 mol) of lauric N-chloramide in 200 ml of tertiary butanol. The resulting mixture was heated to 40° C., and then allowed to react for 30 minutes at this temperature. Any precipitated sodium chloride was removed by filteration and the filtrate was concentrated producing a residue. The residue was taken up in 100 ml of acetone and filtered to yield 24.3 g. (90% yield) of N,N-diethyl-N'-n- undecyl urea of the formula ##STR4## having a melting point of 33°-35° C. and the following analysis:

Workup

  1. additioncontaining 23.35 g
  2. customto react for 30 minutes at this temperature
  3. customAny precipitated sodium chloride was removed by filteration
  4. concentrationthe filtrate was concentrated
  5. customproducing a residue
  6. filtrationfiltered
  7. customto yield 24.3 g

Sources & evidence

ORD record
ord-3cd3589972514c109f3999de3ab2696c
Source dataset
uspto-grants-1982_08
Patent number
US04346233

Reaction notes

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