Water → HCID 18509239, compound

HRID 1356682Notes

Reaction equation

HRID 1356682 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][O:12][CH3:13])(=[O:10])=[O:9])=[CH:4][C:3]=1[C:14]([F:17])([F:16])[F:15].[F:18][C:19]1[CH:20]=[C:21]([N+:26]([O-:28])=[O:27])[CH:22]=[CH:23][C:24]=1F.[H-].[Na+].O>CN(C=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]([O:12][CH3:13])[C:24]2[CH:23]=[CH:22][C:21]([N+:26]([O-:28])=[O:27])=[CH:20][C:19]=2[F:18])(=[O:10])=[O:9])=[CH:4][C:3]=1[C:14]([F:17])([F:15])[F:16]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 1230531,2-Difluoro-4-nitrobenzeneHCID 18509307HCID 18509307, compound

Product 1

HCID 18509239HCID 18509239, compoundYield 37.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-chloro-N-methoxy-3-(trifluoromethyl)benzenesulfonamide(0.58 g (2.00 mmol)) and 3,4-difluoronitrobenzene (0.66 ml (5.96 mmol)) in 5.0 ml of DMF, sodium hydride (60%, 0.09 g (2.25 mmol)) was added bit by bit with stirring under cooling with ice. The resulting mixture was stirred under cooling with ice for one hour and allowed to warm-up to room temperature. Water was added to the reaction mixture and the resulting mixture was extracted with diethyl ether. The extract was washed with water, and dried over anhydrous magnesium sulfate and concentrated under reduced pressure to give 0.32 g (37%) of the title compound as pale yellow crystals.

Workup

  1. temperatureunder cooling with ice
  2. stirringThe resulting mixture was stirred
  3. temperatureunder cooling with ice for one hour
  4. extractionthe resulting mixture was extracted with diethyl ether
  5. washThe extract was washed with water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-153912b4963e4c85bafd9a37a8d9e197
Source dataset
uspto-grants-2003_07
Patent number
US06586617B1

Reaction notes

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