Water → Dioctadecylamine

HRID 480543Notes

Reaction equation

HRID 480543 reaction equation
[CH2:1]([N:19]([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][CH2:37][CH2:38][CH3:39])C#N)[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].O.[OH-].[Na+].C(Cl)(Cl)Cl>OS(O)(=O)=O>[CH2:22]([NH:19][CH2:1][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])[CH2:23][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][CH2:37][CH2:38][CH3:39]

Participants

6

Reactant 4

HCID 962WaterHCID 6212ChloroformHCID 14798Sodium HydroxideHCID 12045608HCID 12045608, compound

Product 1

HCID 66989DioctadecylamineYield 48%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

The crude dioctadecylcyanamide (38 g) was suspended in 2.75 M H2SO4 (150 mL) and the mixture was refluxed for 2.5 h. After cooling to room temperature H2O (100 mL), 30% NaOH (100 mL) and CHCl3 (300 mL) were added. The organic phase was separated, dried and evaporated. The solid residue was suspended in Et2O and stirred for 1 h. The solid was filtered and washed with to give the desired compound (15.3 g; 29.3 mmol). Yield 48%. K.F.: 0.20%. The 1H-NMR, 13C-NMR, MS and IR spectra were consistent with the structure.

Workup

  1. temperaturethe mixture was refluxed for 2.5 h
  2. additionwere added
  3. customThe organic phase was separated
  4. customdried
  5. customevaporated
  6. filtrationThe solid was filtered
  7. washwashed with

Sources & evidence

ORD record
ord-1cb3ff7bdb0642189323a1243eb4fe31
Source dataset
uspto-grants-2003_11
Patent number
US06652834B2

Reaction notes

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