Water → HCID 102166485, compound

HRID 2186440Notes

Reaction equation

HRID 2186440 reaction equation
C(N([CH2:6][CH3:7])CC)C.[C:8]([N:27]=[C:28]=[O:29])(=[O:26])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25].NC(O[CH2:34][CH3:35])=O.[NH2:36][C:37](N)=[O:38].O>O1CCOCC1>[C:8]([NH:27][C:28](=[O:29])[NH:36][C:37](=[O:38])[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:34][CH2:35][CH2:6][CH3:7])(=[O:26])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25]

Participants

7

Reactant 5

HCID 962WaterHCID 1176Urea2×HCID 5641Carbamic acid, ethyl esterHCID 8471TriethylamineHCID 21465855HCID 21465855, compound2×

Product 1

HCID 102166485HCID 102166485, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

0.025 mol of hydroxypropyl cellulose (DS 0.9) and 0.0125 mol of triethylamine are refluxed for 30 minutes in 150 g of dioxane. 0.05 mol of stearoyl isocyanate is then added dropwise and the suspension is stirred under reflux for 9 hours. In the course of this a highly viscous. clear solution is formed. The product is precipitated from acetonitrile, filtered under suction, washed with acetone and dried under a slight vacuum. A white product, which forms a melt of low viscosity at 210° C. and contains bis-stearoyl urea, is obtained in a yield of 93%. (FT-IR: C═O stretching vibration, urethane 1720 cm−1; C═O stretching vibration, urea 1615 cm−1; N—H deformation vibration, urea 1575 cm−1). To control the IR spectra, the bis-stearoyl urea was prepared directly by reacting 0.05 mol of stearoyl isocyanate with 0.1 mol of water in 100 g of dioxane, the precipitated urea was filtered off and the FT-IR spectrum was recorded: (FT-IR: C═O stretching vibration, urea 1615 cm−1; N—H deformation vibration, urea 1575 cm−1).

Workup

  1. temperatureunder reflux for 9 hours
  2. customclear solution is formed
  3. customThe product is precipitated from acetonitrile
  4. filtrationfiltered under suction
  5. washwashed with acetone
  6. customdried under a slight vacuum
  7. customat 210° C.
  8. customis obtained in a yield of 93%
  9. filtrationthe precipitated urea was filtered off

Sources & evidence

ORD record
ord-7d9708e1e5bf42adbc7372a86a5d938c
Source dataset
uspto-grants-2002_06
Patent number
US06403787B2

Reaction notes

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