Hydrochloric Acid → HCID 54002352, compound

HRID 1742198Notes

Reaction equation

HRID 1742198 reaction equation
[Cl:1][C:2]1[CH:25]=[C:24]([C:26]([F:29])([F:28])[F:27])[CH:23]=[C:22]([F:30])[C:3]=1[O:4][C:5]1[CH:21]=[CH:20][C:8]2[N:9]([CH3:19])[C:10](=[O:18])[C:11]([CH3:17])([C:13](=[N:15][OH:16])[CH3:14])[O:12][C:7]=2[CH:6]=1.[H-].[Na+].Br[CH2:34][CH3:35].Cl>CN(C=O)C>[Cl:1][C:2]1[CH:25]=[C:24]([C:26]([F:27])([F:28])[F:29])[CH:23]=[C:22]([F:30])[C:3]=1[O:4][C:5]1[CH:21]=[CH:20][C:8]2[N:9]([CH3:19])[C:10](=[O:18])[C:11]([CH3:17])([C:13](=[N:15][O:16][CH2:34][CH3:35])[CH3:14])[O:12][C:7]=2[CH:6]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6332Ethyl BromideHCID 24758Sodium hydrideHCID 86748071HCID 86748071, compound2×

Product 1

HCID 54002352HCID 54002352, compoundYield 94.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a DMF (10 ml) solution of 7-(2-chloro-6-fluoro-4-trifluoromethylphenoxy)-2,4-dimethyl-2-[1(hydroxyimino)ethyl]-3,4-dihydro-3-oxo-2H-1,4-benzoxazine (Compound 101) (0.3 g) obtained in Example 16 was added, under ice-cooling, 60% sodium hydride (0.03 g), and after stirring for 20 minutes, bromoethane (0.1 g) was dropwise added thereto. After stirring for 2 hours, 1N hydrochloric acid was added and the mixture extracted twice with ethyl acetate (20 ml). The extract was then washed with water and with saturated aqueous sodium chloride, and dried over magnesium sulfate. The solvent was evaporated under a reduced pressure, and the residue purified by silica gel chromatography (eluant: n-hexane/ethyl acetate=4/1) to give 0.3 g of the title compound (colorless oil).

Workup

  1. additionwas added, under ice-
  2. temperaturecooling
  3. extractionthe mixture extracted twice with ethyl acetate (20 ml)
  4. washThe extract was then washed with water and with saturated aqueous sodium chloride
  5. dry with materialdried over magnesium sulfate
  6. customThe solvent was evaporated under a reduced pressure
  7. customthe residue purified by silica gel chromatography (eluant: n-hexane/ethyl acetate=4/1)

Sources & evidence

ORD record
ord-cf87f0f7e4f543a5bc3fbaba4e5d8c1d
Source dataset
uspto-grants-1994_08
Patent number
US05338719

Reaction notes

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