Methyl iodide → 2,2,4-trimethyl-6-nitro-2H-1,4-benzoxazin-3(4H)-one

HRID 238475Notes

Reaction equation

HRID 238475 reaction equation
[CH3:1][C:2]1([CH3:16])[C:7](=[O:8])[NH:6][C:5]2[CH:9]=[C:10]([N+:13]([O-:15])=[O:14])[CH:11]=[CH:12][C:4]=2[O:3]1.CI.[C:19]([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH3:1][C:2]1([CH3:16])[C:7](=[O:8])[N:6]([CH3:19])[C:5]2[CH:9]=[C:10]([N+:13]([O-:15])=[O:14])[CH:11]=[CH:12][C:4]=2[O:3]1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 106566312,2-Dimethyl-6-nitro-2H-benzo[B][1,4]oxazin-3(4H)-one

Product 1

HCID 136655432,2,4-trimethyl-6-nitro-2H-1,4-benzoxazin-3(4H)-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2,2-Dimethyl-6-nitro-4H-benzo[1,4]oxazin-3-one (1.1 g) was mixed with MeI (850 mg, Aldrich), K2CO3 (1.38 g, Aldrich) and DMF (30 ml, Aldrich) at 40° C. for 48 h. The DMF was removed in vacuo and the residue was diluted with EtOAc (80 ml). The organic phase was washed with H2O (50 ml), aqueous Na2SO3 (50 ml) and brine (50 ml). The resulting solution was dried (MgSO4) and concentrated to provide the compound which was used as is.

Workup

  1. customThe DMF was removed in vacuo
  2. additionthe residue was diluted with EtOAc (80 ml)
  3. washThe organic phase was washed with H2O (50 ml), aqueous Na2SO3 (50 ml) and brine (50 ml)
  4. dry with materialThe resulting solution was dried (MgSO4)
  5. concentrationconcentrated
  6. customto provide the compound which

Sources & evidence

ORD record
ord-084d1642d0904ad5a1a2113cf8258135
Source dataset
uspto-grants-2014_02
Patent number
US08642624B2

Reaction notes

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