Water → HCID 18509250, compound

HRID 1356679Notes

Reaction equation

HRID 1356679 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:5]=[C:6]([S:11]([NH:14][O:15][CH3:16])(=[O:13])=[O:12])[CH:7]=[CH:8][C:9]=1[Cl:10].[Cl:17][C:18]1[CH:19]=[C:20]([N+:25]([O-:27])=[O:26])[CH:21]=[CH:22][C:23]=1F.O>CN(C=O)C>[CH3:16][O:15][N:14]([S:11]([C:6]1[CH:7]=[CH:8][C:9]([Cl:10])=[C:4]([Cl:3])[CH:5]=1)(=[O:12])=[O:13])[C:23]1[CH:22]=[CH:21][C:20]([N+:25]([O-:27])=[O:26])=[CH:19][C:18]=1[Cl:17]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 676882-Chloro-1-fluoro-4-nitrobenzeneHCID 18509241HCID 18509241, compound

Product 1

HCID 18509250HCID 18509250, compoundYield 68.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of sodium hydride (60%, 0.09 g (2.25 mmol)) in 3.0 ml of DMF, 3,4-dichloro-N-methoxybenzenesulfonamide (0.56 g (2.19 mmol)) was added with stirring under cooling with ice. To the resulting mixture, after 15 minutes' stirring under cooling with ice, 3-chloro-4-fluoronitrobenzene (0.35 ml (1.99 mmol)) was added and the mixture was stirred for one hour under cooling with ice and 3 hours at room temperature. Then, water was added to the reaction mixture and the resulting mixture was extracted with diethyl ether. The extract was washed twice with water and the ether layer was dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to give 0.56 g (68%) of the title compound as pale yellow-white crystals.

Workup

  1. additionwas added
  2. temperatureunder cooling with ice
  3. stirringTo the resulting mixture, after 15 minutes' stirring
  4. additionwas added
  5. stirringthe mixture was stirred for one hour
  6. extractionthe resulting mixture was extracted with diethyl ether
  7. washThe extract was washed twice with water
  8. dry with materialthe ether layer was dried over anhydrous magnesium sulfate
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-3bd370fca9954ead81020937c934561d
Source dataset
uspto-grants-2003_07
Patent number
US06586617B1

Reaction notes

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