Water → 5-Chloro-N-(4-cyano-2-nitrophenyl)-N-ethyl-2-thiophenesulfonamide

HRID 1356700Notes

Reaction equation

HRID 1356700 reaction equation
[H-].[Na+].[C:3]([C:5]1[CH:13]=[CH:12][C:8]([NH:9][CH2:10][CH3:11])=[C:7]([N+:14]([O-:16])=[O:15])[CH:6]=1)#[N:4].[Cl:17][C:18]1[S:22][C:21]([S:23](Cl)(=[O:25])=[O:24])=[CH:20][CH:19]=1.O>O1CCCC1>[Cl:17][C:18]1[S:22][C:21]([S:23]([N:9]([C:8]2[CH:12]=[CH:13][C:5]([C:3]#[N:4])=[CH:6][C:7]=2[N+:14]([O-:16])=[O:15])[CH2:10][CH3:11])(=[O:25])=[O:24])=[CH:20][CH:19]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 27339255-Chlorothiophene-2-sulfonyl chlorideHCID 31180704-(Ethylamino)-3-nitrobenzonitrile

Product 1

HCID 185093055-Chloro-N-(4-cyano-2-nitrophenyl)-N-ethyl-2-thiophenesulfonamideYield 30%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of sodium hydride (60%, 0.10 g (2.50 mmol)) in tetrahydrofuran (THF) (3.0 ml), 4-cyano-N-ethyl-2-nitroaniline (0.38 g (1.99 mmol)) was added with stirring at room temperature. To the mixture, upon stirring for 15 minutes at room temperature and after the solution had turned deep purple, 5-chloro-2-thiophenesulfonyl chloride (0.55 g (2.53 mmol)) was added and the resulting mixture was stirred at room temperature for 18 hours. The reaction mixture was poured into water and the resulting mixture was extracted with ethyl acetate. The extract was washed with a saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography with ethyl acetate-hexane (1:3) as eluent, to give 0.22 g (30%) of the title compound as yellow crystals.

Workup

  1. additionwas added
  2. stirringTo the mixture, upon stirring for 15 minutes at room temperature
  3. stirringthe resulting mixture was stirred at room temperature for 18 hours
  4. extractionthe resulting mixture was extracted with ethyl acetate
  5. washThe extract was washed with a saturated aqueous solution of sodium chloride
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-2c0a68e092304fa6bc5757233d90e5fb
Source dataset
uspto-grants-2003_07
Patent number
US06586617B1

Reaction notes

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