Potassium Carbonate → HCID 23287861, compound

HRID 367253Notes

Reaction equation

HRID 367253 reaction equation
Br[C:2]1[CH:19]=[CH:18][CH:17]=[CH:16][C:3]=1[O:4][CH2:5][O:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[NH:13]C=O.C(=O)([O-])[O-].[K+].[K+]>C1C=CC(C2C=CC=CC=2)=CC=1.C1C=CC(OC2C=CC=CC=2)=CC=1.[Cu].[Cu](Br)Br>[CH:9]1[C:8]2[NH:13][C:2]3[CH:19]=[CH:18][CH:17]=[CH:16][C:3]=3[O:4][CH2:5][O:6][C:7]=2[CH:12]=[CH:11][CH:10]=1

Participants

6

Reactant 2

HCID 11430Potassium CarbonateHCID 23287862N-{2-[(2-Bromophenoxy)methoxy]phenyl}formamide

Product 1

HCID 23287861HCID 23287861, compoundYield 102.1%

Reagents, catalysts & solvents 3

HCID 23978CopperCatalystHCID 24611Copper bromide (CuBr2)CatalystHCID 246701,1'-Biphenyl, mixt. with 1,1'-oxybis(benzene)Solvent

Conditions

Temperature
180 °C

Procedure

The above formamide (6.8 g, 21 mmol) was suspended in Dowtherm (75 ml), and potassium carbonate (3.9 g, 28 mmol) was added, followed by copper (1.1 g, 17 mmol) and copper bromide (1.5 g, 11 mmol). The reaction mixture was heated at 180° C. overnight. After cooling, the mixture was filtered, and the filtercake was washed with dichloromethane. Dowtherm and solvent was distilled off, and ethanol (200 ml) was added to the residue, which was left overnight. 4 M Sodium hydroxide (14 ml) was added and the mixture was heated at reflux temperature for 1 h. After cooling, the mixture was filtered and evaporated. The residue was suspended in ethyl acetate (200 ml) and water (100 ml). The phases were separated and the organic phase was washed with water (2×75 ml). The aqueous phases were extracted with ethyl acetate (100 ml) and the combined organic extracts were evaporated. The residue was suspended in warm cyclohexane (100 ml), and left cooling under stirring. The precipitated solid was filtered off and dried, affording 12H-dibenzo[d,g][1,3,6]dioxazocine (4.57 g, 50%).

Workup

  1. temperatureAfter cooling
  2. filtrationthe mixture was filtered
  3. washthe filtercake was washed with dichloromethane
  4. distillationDowtherm and solvent was distilled off
  5. additionethanol (200 ml) was added to the residue, which
  6. addition4 M Sodium hydroxide (14 ml) was added
  7. temperaturethe mixture was heated
  8. temperatureat reflux temperature for 1 h
  9. temperatureAfter cooling
  10. filtrationthe mixture was filtered
  11. customevaporated
  12. customThe phases were separated
  13. washthe organic phase was washed with water (2×75 ml)
  14. extractionThe aqueous phases were extracted with ethyl acetate (100 ml)
  15. customthe combined organic extracts were evaporated
  16. waitleft
  17. temperaturecooling
  18. filtrationThe precipitated solid was filtered off
  19. customdried

Sources & evidence

ORD record
ord-68467815a16642faae0b9a63ac35ddc2
Source dataset
uspto-grants-2000_10
Patent number
US06133268

Reaction notes

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