Water → HCID 11726718, compound

HRID 847332Notes

Reaction equation

HRID 847332 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:22]=[C:21]([C:23]([F:26])([F:25])[F:24])[CH:20]=[CH:19][C:5]=1[O:6][C:7]1[CH:18]=[CH:17][C:10]2[NH:11][C:12](=[O:16])[CH:13]([CH3:15])[O:14][C:9]=2[CH:8]=1.[CH3:27]I.O>CN(C)C=O>[Cl:3][C:4]1[CH:22]=[C:21]([C:23]([F:24])([F:25])[F:26])[CH:20]=[CH:19][C:5]=1[O:6][C:7]1[CH:18]=[CH:17][C:10]2[N:11]([CH3:27])[C:12](=[O:16])[CH:13]([CH3:15])[O:14][C:9]=2[CH:8]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 9975627HCID 9975627, compound

Product 1

HCID 11726718HCID 11726718, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

First, 60% sodium hydride (0.2 g) was suspended in dimethylformamide (5 ml), and a solution of 7-(2-chloro -4-trifluoromethylphenoxy)-2-methyl-2H-1,4-benzoxazine-3 (4H)-one (0.4 g) prepared in Example 1 in dimethylformamide (5 ml) was dropwise added thereto while cooling with ice, and the mixture was stirred for 10 min. Then methyl iodide (0.7 g) was added thereto and the mixture was stirred for additional 10 min, and thereafter, water (20 ml) was added thereto to terminate the reaction. The reaction mixture was extracted with ethyl acetate (50 ml×2), washed with water and a saturated saline solution, and then dried over anhydrous magnesium sulfate. The solvent was distilled off in vacuo, and the residue was purified by silica gel column chromatography (developing solvent: n-hexane/ethyl acetate=3/1) to prepare the title compound (0.4 g) as a colorless crystal (yield: 98%).

Workup

  1. temperaturewhile cooling with ice
  2. stirringthe mixture was stirred for additional 10 min
  3. customto terminate
  4. customthe reaction
  5. extractionThe reaction mixture was extracted with ethyl acetate (50 ml×2)
  6. washwashed with water
  7. dry with materiala saturated saline solution, and then dried over anhydrous magnesium sulfate
  8. distillationThe solvent was distilled off in vacuo
  9. customthe residue was purified by silica gel column chromatography (developing solvent: n-hexane/ethyl acetate=3/1)

Sources & evidence

ORD record
ord-1134babbb18947d5bc838464ab834d38
Source dataset
uspto-grants-1992_08
Patent number
US05141551

Reaction notes

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