Water → HCID 18509254, compound

HRID 1356627Notes

Reaction equation

HRID 1356627 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:13]=[CH:12][C:7]([NH:8][CH:9]2[CH2:11][CH2:10]2)=[C:6]([N+:14]([O-:16])=[O:15])[CH:5]=1.[C:17]1([CH3:27])[CH:22]=[CH:21][C:20]([S:23](Cl)(=[O:25])=[O:24])=[CH:19][CH:18]=1.O>CN(C=O)C>[Cl:3][C:4]1[CH:13]=[CH:12][C:7]([N:8]([CH:9]2[CH2:10][CH2:11]2)[S:23]([C:20]2[CH:21]=[CH:22][C:17]([CH3:27])=[CH:18][CH:19]=2)(=[O:25])=[O:24])=[C:6]([N+:14]([O-:16])=[O:15])[CH:5]=1

Participants

6

Reactant 4

HCID 962WaterHCID 73974-Toluenesulfonyl chlorideHCID 24758Sodium hydrideHCID 18509329HCID 18509329, compound

Product 1

HCID 18509254HCID 18509254, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of sodium hydride (60%, 0.10 g (2.50 mmol)) in DMF (3.0 ml), 4-chloro-N-cyclopropyl-2-nitroaniline (0.40 g (1.88 mmol)) was added with stirring at room temperature. To the resulting mixture, after 15 minutes' stirring at room temperature, p-toluenesulfonyl chloride (0.38 g (1.99 mmol)) was added. After one hour's stirring at room temperature, the reaction mixture was 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. The residue was subjected to silica gel chromatography with ethyl acetate-hexane (1:3) as eluent, to give 0.42 g (61%) of the title compound as 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

Sources & evidence

ORD record
ord-20e4a27c6b374ef88d866f8303b581e6
Source dataset
uspto-grants-2003_07
Patent number
US06586617B1

Reaction notes

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