Water → HCID 86687933, compound

HRID 2401479Notes

Reaction equation

HRID 2401479 reaction equation
[Cl:1][C:2]1[C:14]([N+:15]([O-:17])=[O:16])=[CH:13][C:5]2[O:6][C:7]([CH3:12])([CH3:11])[C:8](=[O:10])[NH:9][C:4]=2[CH:3]=1.[H-].[Na+].I[CH3:21].O>CN(C=O)C>[Cl:1][C:2]1[C:14]([N+:15]([O-:17])=[O:16])=[CH:13][C:5]2[O:6][C:7]([CH3:12])([CH3:11])[C:8](=[O:10])[N:9]([CH3:21])[C:4]=2[CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 10848710HCID 10848710, compound

Product 1

HCID 86687933HCID 86687933, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

6-Chloro-2,2-dimethyl-7-nitro-2H-benzo[b][1,4]oxazin-3(4H)-one (2.29 g, 8.9 mmol) was stirred in DMF at 0° C. under an atmosphere of nitrogen then sodium hydride (60% dispersion in oil) (392 mg, 9.79 mmol) was added. The reaction was allowed to stir at room temperature for 30 min then iodomethane (1.89 g, 13.4 mmol) was added and the reaction was stirred at room temperature for 18 h. Analysis by LCMS indicated that the reaction was complete. Water (10 mL) was added carefully then the DMF was removed under reduced pressure. The residue was partitioned between ethyl acetate and water. The layers were separated and the aqueous phase was extracted with ethyl acetate. The organic portions were combined then passed through a phase separation cartridge. The solvents were evaporated to afford an orange solid (2.4 g, quant.) which was taken through to the next step with no further purification.

Workup

  1. stirringthe reaction was stirred at room temperature for 18 h
  2. customthe DMF was removed under reduced pressure
  3. customThe residue was partitioned between ethyl acetate and water
  4. customThe layers were separated
  5. extractionthe aqueous phase was extracted with ethyl acetate
  6. customThe organic portions were combined then passed through a phase separation cartridge
  7. customThe solvents were evaporated
  8. customto afford an orange solid (2.4 g, quant.) which
  9. customwas taken through to the next step with no further purification

Sources & evidence

ORD record
ord-3788f775c15f4ec492c67f8030db7ee8
Source dataset
uspto-grants-2014_08
Patent number
US08796296B2

Reaction notes

Loading…