Water → HCID 18509278, compound

HRID 1356657Notes

Reaction equation

HRID 1356657 reaction equation
[H-].[Na+].[C:3]([C:5]1[CH:21]=[C:20]([N+:22]([O-:24])=[O:23])[CH:19]=[CH:18][C:6]=1[NH:7][S:8]([C:11]1[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][CH:12]=1)(=[O:10])=[O:9])#[N:4].S(OCC)(O[CH2:29][CH3:30])(=O)=O.O>CN(C=O)C>[C:3]([C:5]1[CH:21]=[C:20]([N+:22]([O-:24])=[O:23])[CH:19]=[CH:18][C:6]=1[N:7]([CH2:29][CH3:30])[S:8]([C:11]1[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][CH:12]=1)(=[O:10])=[O:9])#[N:4]

Participants

6

Reactant 4

HCID 962WaterHCID 6163Diethyl SulfateHCID 24758Sodium hydrideHCID 18509253HCID 18509253, compound

Product 1

HCID 18509278HCID 18509278, compoundYield 26.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of sodium hydride (60%, 0.12 g (3.00 mmol)) in 3.0 ml of DMF, 2′-cyano-4′-nitro-p-toluenesulfonanilide (0.80 g (2.52 mmol)) was added with′stirring at room temperature. To the resulting mixture, after 15 minutes' stirring at room temperature, diethyl sulfate (0.40 ml (3.05 mmol)) was added dropwise and the mixture was heated at 80° C. for 2 hours and at 100° C. for 2 hours with stirring. The reaction mixture was then cooled to room temperature, poured into water and extracted with diethyl ether. The extract was washed three times with 1% aqueous sodium hydroxide solution, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography with ethyl acetate-hexane (1:2) as eluent, to give 0.23 g (26%) of the title compound as white crystals.

Workup

  1. additionwas added with′stirring at room temperature
  2. temperaturethe mixture was heated at 80° C. for 2 hours and at 100° C. for 2 hours
  3. stirringwith stirring
  4. temperatureThe reaction mixture was then cooled to room temperature
  5. extractionextracted with diethyl ether
  6. washThe extract was washed three times with 1% aqueous sodium hydroxide solution
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d78092d5b028479cb7ba908569fad193
Source dataset
uspto-grants-2003_07
Patent number
US06586617B1

Reaction notes

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