Potassium Iodide → HCID 19092084, compound

HRID 483334Notes

Reaction equation

HRID 483334 reaction equation
[CH3:1][N:2]1[C:7]2[CH:8]=[C:9](CCCCBr)[CH:10]=[CH:11][C:6]=2[O:5][CH2:4][C:3]1=[O:17].[I-].[K+]>CO.C(Cl)(Cl)Cl>[CH3:1][N:2]1[C:7]2[CH:8]=[CH:9][C:10]([CH2:10][CH2:11][CH2:6][CH2:7][NH2:2])=[CH:11][C:6]=2[O:5][CH2:4][C:3]1=[O:17]

Participants

5

Reactant 2

HCID 4875Potassium IodideHCID 19752234HCID 19752234, compound

Product 1

HCID 19092084HCID 19092084, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6212ChloroformSolvent

Procedure

In a 250 cm3 ground-necked flask, 8.1 g (0.03 mol) of 4-methyl-6-(4-bromobutyl)2,3-dihydro-3-oxo-1,4-benzoxazine and 0.9 g of potassium iodide are dissolved in 120 cm3 of methanol and 30 cm3 of chloroform. A stream of gaseous ammonia is bubbled into the solution to the point of saturation, equivalent to approximately 2.6 g of ammonia, and a reflux condenser is then fitted. The temperature is stabilized at 50° C. with an oil bath and the mixture is left stirring magnetically for 72 hours. After cooling, the reaction mixture is evaporated on a water bath under vacuum. The residue is ground with distilled water acidified with 5% HCl solution, and then drained. The filtrate is recovered, washed with ethyl acetate and then alkalinized with 10% sodium hydroxide solution. It is extracted with chloroform, leaving the 2 phases agitating for 1/2 hour, and the organic phase is washed with distilled water and then dried over calcium chloride. The organic phase is evaporated on a water bath under vacuum, the residue is then taken up in absolute ethanol, a stream of gaseous HCl is bubbled through and the mixture is then evaporated to dryness on a water bath under vacuum. The product is dried and then recrystallized in absolute ethanol.

Workup

  1. customA stream of gaseous ammonia is bubbled into the solution to the point of saturation, equivalent to approximately 2.6 g of ammonia, and a reflux condenser
  2. customis then fitted
  3. customThe temperature is stabilized at 50° C. with an oil bath
  4. waitthe mixture is left
  5. temperatureAfter cooling
  6. customthe reaction mixture is evaporated on a water bath under vacuum
  7. customThe filtrate is recovered
  8. washwashed with ethyl acetate
  9. extractionIt is extracted with chloroform
  10. customleaving the 2 phases
  11. stirringagitating for 1/2 hour
  12. washthe organic phase is washed with distilled water
  13. dry with materialdried over calcium chloride
  14. customThe organic phase is evaporated on a water bath under vacuum
  15. customa stream of gaseous HCl is bubbled through and the mixture
  16. customis then evaporated to dryness on a water bath under vacuum
  17. customThe product is dried
  18. customrecrystallized in absolute ethanol

Sources & evidence

ORD record
ord-79f7b9d76bcb42e386334a70a1a188ae
Source dataset
uspto-grants-1993_07
Patent number
US05225409

Reaction notes

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