Water → HCID 131720256, compound

HRID 1489775Notes

Reaction equation

HRID 1489775 reaction equation
[CH:1]1[C:11]2[CH:10]([CH2:12][OH:13])[C:9]3[CH:14]=[CH:15][CH:16]=[CH:17][C:8]=3[CH2:7][O:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.C([N:20]([CH2:23]C)[CH2:21][CH3:22])C.[OH2:25]>ClCCl>[CH:1]1[C:11]2[CH:10]([CH2:12][O:13][C:23](=[O:25])[NH:20][C:21]3[C:22]([CH:8]([CH3:17])[CH3:7])=[CH:3][CH:2]=[CH:1][C:11]=3[CH:10]([CH3:12])[CH3:9])[C:9]3[CH:14]=[CH:15][CH:16]=[CH:17][C:8]=3[CH2:7][O:6][C:5]=2[CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 962WaterHCID 8471TriethylamineHCID 22902443HCID 22902443, compound

Product 1

HCID 131720256HCID 131720256, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1.1 g of 6,11-dihydrodibenz[b,e]oxepin-11-methanol was dissolved in 30 ml of dichloromethane, and 2.7 ml of triethylamine and 2.3 ml of 2,6-diisopropyl isocyanate were added thereto with cooling on ice. The mixture was stirred for 15 hours at room temperature, and 100 ml of water was added to the reaction mixture, and then extracted with dichloromethane. The thus obtained organic layer was washed first with 1N hydrochloric acid and then with a saturated saline solution, dried and concentrated to dryness under reduced pressure. The solid residue was purified by silica gel column chromatography (using an eluting solvent of 1/9 (v/v) ethyl acetate/toluene). The crude product was recrystallized from ethyl acetate to obtain 0.97 g of Compound 6.

Workup

  1. temperaturewith cooling on ice
  2. extractionextracted with dichloromethane
  3. washThe thus obtained organic layer was washed first with 1N hydrochloric acid
  4. customwith a saturated saline solution, dried
  5. concentrationconcentrated to dryness under reduced pressure
  6. customThe solid residue was purified by silica gel column chromatography (
  7. customThe crude product was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-a2db3e68c3e04f34ab7bc095f5cfa4a5
Source dataset
uspto-grants-1997_10
Patent number
US05679703

Reaction notes

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