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

HRID 1176691Notes

Reaction equation

HRID 1176691 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)=CC1C=CC=CC=1.[O:20]=[O+][O-].S(C)C>C(Cl)Cl>[O:19]=[C:15]1[CH2:14][O:13][C:12]2[CH:11]=[CH:10][C:9]([CH:1]=[O:20])=[N:18][C:17]=2[NH:16]1

Participants

5

Reactant 3

HCID 1068Dimethyl SulfideHCID 24823OzoneHCID 684438466-Styryl-4H-pyrido[3,2-b][1,4]oxazin-3-one

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 6-styryl-4H-pyrido[3,2-b][1,4]oxazin-3-one (757 mg, 3.00 mmol) in CH2Cl2 (128 mL) was bubbled ozone at −78° C. with stirring until a pale blue color appeared. The excess ozone was removed by bubbling oxygen through the reaction mixture for 15 min. Me2S (1.0 mL, 14 mmol) was added, and the reaction was stirred at −78° C. for 3 h and then at RT for 24 h. The solvent was concentrated and the residue was triturated with Et2O (100 mL). The solid collected from filtration of the suspension was washed with additional Et2O and dried in vacuo to provide 340 mg (63% crude) of a solid, which was used without further purification. MS (ESI): exact mass calculated for C8H6N2O3, 178.04; m/z found, 179.2 [M+H]+.

Workup

  1. customThe excess ozone was removed
  2. customby bubbling oxygen through the reaction mixture for 15 min
  3. stirringthe reaction was stirred at −78° C. for 3 h
  4. concentrationThe solvent was concentrated
  5. customthe residue was triturated with Et2O (100 mL)
  6. filtrationThe solid collected from filtration of the suspension
  7. washwas washed with additional Et2O
  8. customdried in vacuo
  9. customto provide 340 mg (63% crude) of a solid, which
  10. customwas used without further purification

Sources & evidence

ORD record
ord-47bd1e74cb2e40dbaea8fd0c3dcaa377
Source dataset
uspto-grants-2010_11
Patent number
US07842810B2

Reaction notes

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