Dimethyl Sulfide → 3-Oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazine-6-carbaldehyde

HRID 2233333Notes

Reaction equation

HRID 2233333 reaction equation
[CH:1](/[C:9]1[CH:10]=[CH:11][C:12]2[O:13][CH2:14][C:15](=[O:19])[NH:16][C:17]=2[N:18]=1)=C\C1C=CC=CC=1.CSC.C(Cl)Cl.C[OH:27]>>[O:19]=[C:15]1[CH2:14][O:13][C:12]2[CH:11]=[CH:10][C:9]([CH:1]=[O:27])=[N:18][C:17]=2[NH:16]1

Participants

4

Reactant 3

HCID 1068Dimethyl SulfideHCID 21226129Dichloromethane methanolHCID 21873663HCID 21873663, compound

Product 1

HCID 218737373-Oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazine-6-carbaldehydeYield 77%

Conditions

Temperature
-78 °C

Procedure

6-((E)-Styryl)-4H-pyrido[3,2-b][1,4]oxazin-3-one (6.2 g, 27 mmole) was dissolved in 5:1 CH2Cl2/MeOH (500 mL) and the solution was cooled to −78° C. Ozone was bubbled through the solution with stirring until a pale blue color appeared, then the excess ozone was removed by bubbling oxygen through the solution for 15 min. Dimethylsulfide (9.9 mL, 135 mmole) was added to the solution, and the reaction was stirred at −78° C. for 3 hr, then at RT overnight. The solvent was removed in vacuo, and the residue was triturated and stirred with Et2O (150 mL). The solid was collected, washed with additional Et2O, and dried to afford the title compound (3.4 g, 77%): MS (ES) m/e 179.0 (M+H)+.

Workup

  1. customOzone was bubbled through the solution
  2. customthe excess ozone was removed
  3. customby bubbling oxygen through the solution for 15 min
  4. stirringthe reaction was stirred at −78° C. for 3 hr
  5. customat RT
  6. customovernight
  7. customThe solvent was removed in vacuo
  8. customthe residue was triturated
  9. stirringstirred with Et2O (150 mL)
  10. customThe solid was collected
  11. washwashed with additional Et2O
  12. customdried

Sources & evidence

ORD record
ord-5d1616606ffe410ebb9d26828eb45155
Source dataset
uspto-grants-2010_05
Patent number
US07709496B2

Reaction notes

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