Triethylamine → HCID 53975722, compound

HRID 1090885Notes

Reaction equation

HRID 1090885 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 53975722HCID 53975722, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Dodecylisocyanate (105 mg, 0.49 mmol) was added to a solution of 4-aminomethyl-2-triethylsilylfuran (Compound 2, 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-e5ab4637f585402494b2fac6f86aa150
Source dataset
uspto-grants-1992_01
Patent number
US05082954

Reaction notes

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