Triethylamine → 4-(N-Dodecylureido)methyl-2-triethylsilylfuran

HRID 2247840Notes

Reaction equation

HRID 2247840 reaction equation
[CH2:1]([N:13]=[C:14]=[O:15])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].N[CH2:17][C:18]1[CH:19]=[C:20]([Si:23]([CH2:28][CH3:29])([CH2:26][CH3:27])[CH2:24][CH3:25])[O:21][CH:22]=1.C([N:32](CC)CC)C>O1CCCC1>[CH2:1]([N:13]([CH2:17][C:18]1[CH:19]=[C:20]([Si:23]([CH2:24][CH3:25])([CH2:28][CH3:29])[CH2:26][CH3:27])[O:21][CH:22]=1)[C:14]([NH2:32])=[O:15])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 77873Dodecane, 1-isocyanato-HCID 150370494-Aminomethyl-2-triethylsilylfuran2×

Product 1

HCID 539757224-(N-Dodecylureido)methyl-2-triethylsilylfuran

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Dodecylisocyanate (105 mg, 0.49 mmol) was added to a solution of 4-aminomethyl-2-triethylsilylfuran (compound 29, 70 mg, 0.33 mmol) and triethylamine (69 microliter, 0.49 mmol) in tetrahydrofuran (3 ml) at room temperature. After stirring at room temperature overnight (ca. 16 hours), the reaction mixture was quenched with water. Extraction (ethyl ether) and evaporation of the dried (magnesium sulfate) extracts gave a residue which was purified by flash chromatography on silica using 60% ethyl ether/hexane. Fractions of Rf of about 0.47 on evaporation gave the title urea as an off-white solid.

Workup

  1. customthe reaction mixture was quenched with water
  2. extractionExtraction (ethyl ether) and evaporation of the
  3. dry with materialdried (magnesium sulfate)
  4. customextracts gave a residue which
  5. customwas purified by flash chromatography on silica using 60% ethyl ether/hexane
  6. customFractions of Rf of about 0.47 on evaporation

Sources & evidence

ORD record
ord-2414a861f0fe4a78b79e8147dc448fed
Source dataset
uspto-grants-1991_08
Patent number
US05037811

Reaction notes

Loading…