Cyclohexylamine → 1-Cyclohexyl-3-methacryloxyethyl urea

HRID 1684270Notes

Reaction equation

HRID 1684270 reaction equation
[C:1]([O:6][CH2:7][CH2:8][N:9]=[C:10]=[O:11])(=[O:5])[C:2]([CH3:4])=[CH2:3].C1C=C2C=CC(O)=C(C3C4C(=CC=CC=4)C=CC=3O)C2=CC=1.[CH:34]1([NH2:40])[CH2:39][CH2:38][CH2:37][CH2:36][CH2:35]1.C([O-])(=O)CCCCCCCCCCC.C([O-])(=O)CCCCCCCCCCC.C([Sn+2]CCCC)CCC>C(Cl)Cl>[CH:34]1([NH:40][C:10]([NH:9][CH2:8][CH2:7][O:6][C:1](=[O:5])[C:2]([CH3:4])=[CH2:3])=[O:11])[CH2:39][CH2:38][CH2:37][CH2:36][CH2:35]1

Participants

6

Reactant 4

HCID 7965CyclohexylamineHCID 11762BinolHCID 354092-Isocyanatoethyl methacrylateHCID 9809426Di-n-butyldilauryltin

Product 1

HCID 542409741-Cyclohexyl-3-methacryloxyethyl urea

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A 3-neck, 250-mL round bottom flask equipped with a reflux condenser was charged with isocyanatoethyl methacrylate (7.79 g), 1,1'-bi-2-naphthol (1.3 mg) and 50 mL of methylene chloride. While stirring, cyclohexylamine (5.24 g) and dibutyltin dilaurate (52.3 mg) in 50 mL of methylene chloride were added over a 15 minute period. The reaction mixture was kept stirred for an additional 30 minutes. The solution was filtered and evaporated to dryness to recover the product. The product was characterized by H-NMR, 0.72-2.10 ppm (m, 1H), 1.90 ppm (s, 3H), 3.45 ppm (t, 2H), 3.50 ppm (hidden, 1H), 4.18 ppm (t, 2H), 5.12 ppm (s, 1H), 5.26 ppm (s, 1H), 5.52 ppm (s, 1H), 6.10 ppm (s, 1H).

Workup

  1. customA 3-neck, 250-mL round bottom flask equipped with a reflux condenser
  2. stirringThe reaction mixture was kept stirred for an additional 30 minutes
  3. filtrationThe solution was filtered
  4. customevaporated to dryness
  5. customto recover the product

Sources & evidence

ORD record
ord-563a60be14ea4af281a1cf4784f126d9
Source dataset
uspto-grants-1997_06
Patent number
US05639908

Reaction notes

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