Water → HCID 19008610, compound

HRID 1742187Notes

Reaction equation

HRID 1742187 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:26]=[C:25]([C:27]([F:30])([F:29])[F:28])[CH:24]=[CH:23][C:5]=1[O:6][C:7]1[CH:22]=[CH:21][C:10]2[NH:11][C:12](=[O:20])[CH:13]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[O:14][C:9]=2[CH:8]=1.[CH3:31]I.O>CN(C)C=O>[Cl:3][C:4]1[CH:26]=[C:25]([C:27]([F:28])([F:29])[F:30])[CH:24]=[CH:23][C:5]=1[O:6][C:7]1[CH:22]=[CH:21][C:10]2[N:11]([CH3:31])[C:12](=[O:20])[CH:13]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[O:14][C:9]=2[CH:8]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 19008596HCID 19008596, compound2×

Product 1

HCID 19008610HCID 19008610, compoundYield 48.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

60% Sodium hydride (1.0 g) was suspended in dimethylformamide (hereinafter abbreviated as DMF) (5 ml) and under ice-cooling, a DMF solution (5 ml) of ethyl 7-(2-chloro-4-trifluoromethylphenoxy)-3,4-dihydro-3-oxo-2H-1,4-benzoxazine-2-carboxylate (Compound 1) (0.8 g) was dropwise added thereto, followed by stirring for 10 minutes. Methyl iodide (0.4 g) was then added, the mixture was further stirred for 10 minutes, and to the reaction mixture was added water (20 ml) and the mixture was extracted twice with ethyl acetate (50 ml). The extract was washed with water and then saturated aqueous sodium chloride, and dried over magnesium sulfate. The solvent was then evaporated under a reduced pressure and the residue was purified by silica gel chromatography (eluant: n-hexane/ethyl acetate=3/1) to give 0.4 g of the title compound (colorless oil).

Workup

  1. temperatureunder ice-cooling
  2. stirringthe mixture was further stirred for 10 minutes
  3. extractionthe mixture was extracted twice with ethyl acetate (50 ml)
  4. washThe extract was washed with water
  5. dry with materialsaturated aqueous sodium chloride, and dried over magnesium sulfate
  6. customThe solvent was then evaporated under a reduced pressure
  7. customthe residue was purified by silica gel chromatography (eluant: n-hexane/ethyl acetate=3/1)

Sources & evidence

ORD record
ord-24fef3739ba7443ca80f63544d05c527
Source dataset
uspto-grants-1994_08
Patent number
US05338719

Reaction notes

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