Water → 2,4-diethyl-7-methoxycarbonyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazine

HRID 234905Notes

Reaction equation

HRID 234905 reaction equation
[CH2:1]([CH:3]1[C:8](=[O:9])[NH:7][C:6]2[CH:10]=[CH:11][C:12]([C:14]([O:16][CH3:17])=[O:15])=[CH:13][C:5]=2[O:4]1)[CH3:2].[H-].[Na+].[CH2:20](I)[CH3:21].O>CN(C)C=O.C(OCC)(=O)C>[CH2:1]([CH:3]1[C:8](=[O:9])[N:7]([CH2:20][CH3:21])[C:6]2[CH:10]=[CH:11][C:12]([C:14]([O:16][CH3:17])=[O:15])=[CH:13][C:5]=2[O:4]1)[CH3:2]

Participants

7

Reactant 4

HCID 962WaterHCID 6340IodoethaneHCID 24758Sodium hydrideHCID 233531642-ethyl-7-methoxycarbonyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazine

Product 1

HCID 233531632,4-diethyl-7-methoxycarbonyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazineYield 89.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-ethyl-7-methoxycarbonyl-3-oxo-3,4-dihydro-2-H-1,4-benzoxazine [prepared in Preparation 9(1)] (6.0 g) in dimethylformamide (60 ml) were added 60% sodium hydride (in oil) (1.02 g) and ethyl iodide (4.37 g) and the mixture was stirred at room temperature for 2 hours. Water was added to the reaction solution and extraction with ethyl acetate was conducted. The solvent was distilled off under reduced pressure and the resulting residue was subjected to purification by column chromatography using ethyl acetate/hexane [1:4 (v/v)] to give 2,4-diethyl-7-methoxycarbonyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazine (6.0 g).

Workup

  1. distillationThe solvent was distilled off under reduced pressure
  2. customthe resulting residue was subjected to purification by column chromatography

Sources & evidence

ORD record
ord-a2815266b44449a9b1ea17b59a297c5c
Source dataset
uspto-grants-1997_01
Patent number
US05597820

Reaction notes

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