N,N-Diethylaniline → HCID 22992851, compound

HRID 1168580Notes

Reaction equation

HRID 1168580 reaction equation
[Cl:1][C:2]1[CH:14]=[CH:13][C:5]2[C:6](=[O:12])[NH:7][C:8](=O)[CH2:9][O:10][C:4]=2[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:22][CH2:23][CH2:24][CH2:25][Cl:26].C(N(CC)C1C=CC=CC=1)C.P(Cl)(Cl)([Cl:40])=O>CC(C)=O>[Cl:26][CH2:25][CH2:24][CH2:23][CH2:22][N:7]1[C:6](=[O:12])[C:5]2[CH:13]=[CH:14][C:2]([Cl:1])=[CH:3][C:4]=2[O:10][CH:9]=[C:8]1[Cl:40]

Participants

7

Reactant 5

HCID 7061N,N-DiethylanilineHCID 11430Potassium CarbonateHCID 24813Phosphorus oxychlorideHCID 813641-Bromo-4-chlorobutaneHCID 22992846HCID 22992846, compound

Product 1

HCID 22992851HCID 22992851, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
90 °C

Procedure

918 mg of 8-chloro-2,3,4,5-tetrahydro-1,4-benzoxazepine-3,5-dione was dissolved in 20 ml of acetone, 1.2 g (2 equivalents) of potassium carbonate and 819 mg (1.1 equivalents) of 1-bromo-4-chlorobutane were added, and the mixture heated and refluxed for 7 hours. The resultant mixture was allowed to cool, then filtered. The filtrate was condensed and the residue obtained was dissolved in 2 ml of phosphorus oxychloride. Further, 1.4 ml (2 equivalents) of N,N-diethylaniline was added and the mixture was stirred at 90° C. for 12 hours. The phosphorus oxychloride was distilled off and a 10% sodium hydroxide aqueous solution added under ice cooling. The mixture was extracted with methylene chloride, then was washed with a saturated aqueous solution of potassium bicarbonate and saturated saline and dried over anhydrous magnesium sulfate. The solvent was distilled off and the crude product obtained was purified by silica gel column chromatograph (hexane:ethyl acetate=6:1) to obtain 598 mg of the above-identified compound (yield 43%).

Workup

  1. temperaturethe mixture heated
  2. temperaturerefluxed for 7 hours
  3. temperatureto cool
  4. filtrationfiltered
  5. customcondensed
  6. customthe residue obtained
  7. distillationThe phosphorus oxychloride was distilled off
  8. additiona 10% sodium hydroxide aqueous solution added under ice cooling
  9. extractionThe mixture was extracted with methylene chloride
  10. washwas washed with a saturated aqueous solution of potassium bicarbonate and saturated saline
  11. dry with materialdried over anhydrous magnesium sulfate
  12. distillationThe solvent was distilled off
  13. customthe crude product obtained
  14. customwas purified by silica gel column chromatograph (hexane:ethyl acetate=6:1)

Sources & evidence

ORD record
ord-719f6b03b5f947c1b5ec904b969b9801
Source dataset
uspto-grants-2003_09
Patent number
US06624308B2

Reaction notes

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