Water → HCID 18509324, compound

HRID 1356621Notes

Reaction equation

HRID 1356621 reaction equation
[H-].[Na+].[CH3:3][O:4][C:5]1[CH:21]=[CH:20][C:8]([NH:9][S:10]([C:13]2[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=2)(=[O:12])=[O:11])=[C:7]([N+:22]([O-:24])=[O:23])[CH:6]=1.[C:25](OC(=O)C)(=[O:27])[CH3:26].O>CN(C=O)C>[C:25]([N:9]([S:10]([C:13]1[CH:14]=[CH:15][C:16]([CH3:19])=[CH:17][CH:18]=1)(=[O:12])=[O:11])[C:8]1[CH:20]=[CH:21][C:5]([O:4][CH3:3])=[CH:6][C:7]=1[N+:22]([O-:24])=[O:23])(=[O:27])[CH3:26]

Participants

6

Reactant 4

HCID 962WaterHCID 7918Acetic AnhydrideHCID 24758Sodium hydrideHCID 225676N-(4-Methoxy-2-nitrophenyl)-4-methylbenzenesulfonamide

Product 1

HCID 18509324HCID 18509324, compoundYield 90.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of sodium hydride (60%, 0.08 g (2.00 mmol)) in DMF (3.0 ml), 4′-methoxy-2′-nitro-p-toluenesulfonanilide (0.50 g (1.55 mmol)) was added with stirring at room temperature. To the resulting mixture, after 15 minutes' stirring at room temperature, acetic anhydride (0.20 ml (2.12 mmol)) was added dropwise. After one hour's stirring at room temperature, water was poured into the reaction mixture 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. Crystals separated was added to diethyl ether, filtered and washed to give 0.51 g (90%) of the title compound as pale yellow crystals.

Workup

  1. additionwas added
  2. stirringTo the resulting mixture, after 15 minutes' stirring at room temperature
  3. stirringAfter one hour's stirring at room temperature
  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. customCrystals separated
  9. additionwas added to diethyl ether
  10. filtrationfiltered
  11. washwashed

Sources & evidence

ORD record
ord-62ebf695ebc14892a939071209b28080
Source dataset
uspto-grants-2003_07
Patent number
US06586617B1

Reaction notes

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