Water → HCID 18509337, compound

HRID 1356633Notes

Reaction equation

HRID 1356633 reaction equation
[H-].[Na+].[CH3:3][NH:4][S:5]([C:8]1[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=1)(=[O:7])=[O:6].F[C:16]1[CH:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[CH:18][C:17]=1[CH3:25].O>CN(C=O)C>[CH3:3][N:4]([S:5]([C:8]1[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=1)(=[O:6])=[O:7])[C:16]1[CH:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[CH:18][C:17]=1[CH3:25]

Participants

6

Reactant 4

HCID 962WaterHCID 12543Benzenesulfonamide, N,4-dimethyl-HCID 24758Sodium hydrideHCID 68001Benzene, 1-fluoro-2-methyl-4-nitro-

Product 1

HCID 18509337HCID 18509337, compoundYield 36%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of sodium hydride (60%, 0.08 g (2.00 mmol)) in 2.0 ml of DMF, N-methyl-p-toluenesulfonamide (0.37 g (2.00 mmol)) was added at room temperature with stirring. To the resulting mixture, after 15 minutes' stirring at room temperature, 2-fluoro-5-nitrotoluene (0.31 g (2.00 mmol)) was added. The reaction mixture was stirred at room temperature for 2 hours, poured into water and extracted with ethyl acetate. The extract was washed with water and saturated sodium chloride solution, successively, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. Diisopropyl ether was added to the residue and crystals separated was filtered and washed to give 0.22 g (36%) of the title compound as pale yellow crystals.

Workup

  1. additionwas added at room temperature
  2. stirringTo the resulting mixture, after 15 minutes' stirring at room temperature
  3. stirringThe reaction mixture was stirred at room temperature for 2 hours
  4. extractionextracted with ethyl acetate
  5. washThe extract was washed with water and saturated sodium chloride solution
  6. dry with materialsuccessively, dried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. additionDiisopropyl ether was added to the residue and crystals
  9. customseparated
  10. filtrationwas filtered
  11. washwashed

Sources & evidence

ORD record
ord-f5cc8aaae2694afe9de949247bce8ef6
Source dataset
uspto-grants-2003_07
Patent number
US06586617B1

Reaction notes

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