Dimethylformamide → Ethyl 3,4-dihydro-2,4-dimethyl-3-oxo-2H-1,4-benzoxazine-2-carboxylate

HRID 1106466Notes

Reaction equation

HRID 1106466 reaction equation
[CH2:1]([O:3][C:4]([CH:6]1[C:11](=O)N[C:9]2[CH:13]=[CH:14][CH:15]=C[C:8]=2[O:7]1)=[O:5])[CH3:2].[H-].[Na+].IC.C(OCC)(=O)C.[CH3:27][N:28]([CH3:31])[CH:29]=[O:30]>>[CH3:11][C:6]1([C:4]([O:3][CH2:1][CH3:2])=[O:5])[C:29](=[O:30])[N:28]([CH3:31])[C:27]2[CH:15]=[CH:14][CH:13]=[CH:9][C:8]=2[O:7]1

Participants

6

Reactant 5

HCID 6228Dimethylformamide2×HCID 6328Methyl iodideHCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 11790749HCID 11790749, compound

Product 1

HCID 21765025Ethyl 3,4-dihydro-2,4-dimethyl-3-oxo-2H-1,4-benzoxazine-2-carboxylate

Conditions

Temperature
0 °C

Procedure

5.5 mmol (1.2 g) of 2-ethoxycarbonyl-3,4-dihydro-2H-1,4-benzoxazin-3-one (described in C.R. Acad. Sci. Paris Series C, 1969, 269, 154) in 5 ml of dimethylformamide are added at 0° C. to a suspension of 11 mmol (0.44 g) of 60% sodium hydride in 5 ml of dimethyformamide. The reaction mixture is stirred at 0° C. for 30 minutes. 22.2 mmol (1.38 ml) of iodomethane are then added, and the reaction mixture is stirred at room temperature for 1 hour. After hydrolysis and extraction with ethyl acetate, the organic phase is dried, concentrated and purified by chromatography on silica gel using an ethyl acetate/petroleum ether mixture (3/7) as eluant to yield the expected compound.

Workup

  1. stirringthe reaction mixture is stirred at room temperature for 1 hour
  2. customthe organic phase is dried
  3. concentrationconcentrated
  4. custompurified by chromatography on silica gel using an ethyl acetate/petroleum ether mixture (3/7) as eluant

Sources & evidence

ORD record
ord-e36a2919eef143c488fd3d78559a4988
Source dataset
uspto-grants-2000_05
Patent number
US06057317

Reaction notes

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