Water → HCID 18509236, compound

HRID 1356685Notes

Reaction equation

HRID 1356685 reaction equation
[Cl:1][C:2]1[S:6][C:5]([S:7]([NH:10][O:11][CH3:12])(=[O:9])=[O:8])=[CH:4][CH:3]=1.Cl[C:14]1[CH:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[CH:18][C:15]=1[C:16]#[N:17].[H-].[Na+].O>CN(C=O)C>[Cl:1][C:2]1[S:6][C:5]([S:7]([N:10]([C:14]2[CH:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[CH:18][C:15]=2[C:16]#[N:17])[O:11][CH3:12])(=[O:9])=[O:8])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 855042-Chloro-5-nitrobenzonitrileHCID 18509246HCID 18509246, compound

Product 1

HCID 18509236HCID 18509236, compoundYield 54.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-chloro-N-methoxy-2-thiophenesulfonamide (0.46 g (2.02 mmol)) and 2-chloro-5-nitrobenzonitrile (0.45 g (2.46 mol)) in DMF (3.0 ml), sodium hydride (60%, 0.09 g (2.25 mmol)) was added bit by bit under cooling with ice and with stirring and the mixture was stirred under cooling with ice for one hour and at room temperature for one hour. Water was added to the reaction mixture and the resulting mixture was extracted with ethyl acetate. The extract was washed with water, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue was subjected to silica gel chromatography with ethyl acetate-hexane (1:3) as eluent to give 0.41 g (54%) of the title compound as pale yellow crystals.

Workup

  1. temperatureunder cooling with ice
  2. stirringthe mixture was stirred
  3. extractionthe resulting mixture was extracted with ethyl acetate
  4. washThe extract was washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-0591e95d5e474a8baa4c24102c10ab0b
Source dataset
uspto-grants-2003_07
Patent number
US06586617B1

Reaction notes

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