Methyl iodide → 4,4-diethyl-1-methyl-6-nitro-1,4-dihydro-2H-3,1-benzoxazin-2-one

HRID 899196Notes

Reaction equation

HRID 899196 reaction equation
[CH2:1]([C:3]1([CH2:17][CH3:18])[C:8]2[CH:9]=[C:10]([N+:13]([O-:15])=[O:14])[CH:11]=[CH:12][C:7]=2[NH:6][C:5](=[O:16])[O:4]1)[CH3:2].[H-].[Na+].[CH3:21]I>CN(C=O)C>[CH2:17]([C:3]1([CH2:1][CH3:2])[C:8]2[CH:9]=[C:10]([N+:13]([O-:15])=[O:14])[CH:11]=[CH:12][C:7]=2[N:6]([CH3:21])[C:5](=[O:16])[O:4]1)[CH3:18]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 200420994,4-diethyl-6-nitro-1,4-dihydro-2H-3,1-benzoxazin-2-one

Product 1

HCID 692165584,4-diethyl-1-methyl-6-nitro-1,4-dihydro-2H-3,1-benzoxazin-2-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 4,4-diethyl-6-nitro-1,4-dihydro-2H-3,1-benzoxazin-2-one (5.00 g, 19.98 mmol) in DMF (30 mL) at 0° C. was added sodium hydride (1.20 g-60%, 29.97 mmol). After 20 minutes, methyl iodide (3.8 mL, 61.00 mmol) was added and the reaction was warmed to room temperature. After stirring for one hour, the reaction was quenched with ammonium chloride (sat.) and extracted with ethyl acetate (3×50 mL). The combined organic layers were washed with brine repeatedly and dried over magnesium sulfate. Solvent was removed and the residue was triturated with ether to give 4,4-diethyl-1-methyl-6-nitro-1,4-dihydro-2H-3,1-benzoxazin-2-one a yellowish-white solid (3.74 g, 71%). 1H NMR (DMSO-d6): δ 8.27 (dd, J=9.0, 2.6 Hz, 1H), 8.05 (d, J=2.6 Hz, 1H), 7.34 (d, J=9.0 Hz, 1H), 3.37 (s, 3H), 2.15 (m, 4H), 0.80 (t, J=7.3 Hz, 6H); MS (ESI) m/z 265 ([M+H]+); Anal. calcd for C13H16N2O4: C, 59.08; H, 6.10; N, 10.60. Found: C, 59.62; H, 6.20; N, 10.48.

Workup

  1. customthe reaction was quenched with ammonium chloride (sat.)
  2. extractionextracted with ethyl acetate (3×50 mL)
  3. washThe combined organic layers were washed with brine repeatedly
  4. dry with materialdried over magnesium sulfate
  5. customSolvent was removed
  6. customthe residue was triturated with ether

Sources & evidence

ORD record
ord-9095ba5b55eb43d5aa48a2207fd2f9a1
Source dataset
uspto-grants-2008_04
Patent number
US07354915B2

Reaction notes

Loading…