Potassium Carbonate → HCID 11066036, compound

HRID 1870476Notes

Reaction equation

HRID 1870476 reaction equation
[O:1]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[C:5](=[O:12])[NH:4][C:3](=O)[CH2:2]1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:21][CH2:22][CH2:23][CH2:24][Cl:25].O1CCOCC1.[ClH:32]>CC(C)=O.P(Cl)(Cl)(Cl)=O>[Cl:32][C:3]1[N:4]([CH2:21][CH2:22][CH2:23][CH2:24][Cl:25])[C:5](=[O:12])[C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=2[O:1][CH:2]=1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 813641-Bromo-4-chlorobutaneHCID 7266301,4-benzoxazepine-3,5(2H,4H)-dioneHCID 204431481,4-Dioxane hydrochloride

Product 1

HCID 11066036HCID 11066036, compoundYield 45%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 24813Phosphorus oxychlorideSolvent

Conditions

Temperature
100 °C

Procedure

5.0 g of 2,3,4,5-tetrahydro-1,4-benzoxazepine-3,5-dione was dissolved in 100 ml of acetone, 7.8 g (2 equivalents) of potassium carbonate and 6.5 ml (2 equivalents) of 1-bromo-4-chlorobutane were added, and the mixture heated and refluxed for 8 hours. The resultant mixture was allowed to cool, then filtered. The filtrate was concentrated and the residue obtained was dissolved in 50 ml of phosphorus oxychloride. Further, 20 ml of 4N hydrochloride dioxane-solution was added and the mixture stirred at 100° C. for 25 hours. The phosphorus oxychloride was distilled off and a 10% aqueous sodium hydroxide 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 4.4 g of the above-identified compound (yield 45%).

Workup

  1. temperaturethe mixture heated
  2. temperaturerefluxed for 8 hours
  3. temperatureto cool
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated
  6. customthe residue obtained
  7. distillationThe phosphorus oxychloride was distilled off
  8. additiona 10% aqueous sodium hydroxide 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-7d3a748fb5ca4aafb1fe527261f4e428
Source dataset
uspto-grants-2000_08
Patent number
US06096884

Reaction notes

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