Sodium hydride → HCID 18509210, compound

HRID 1356688Notes

Reaction equation

HRID 1356688 reaction equation
[H-].[Na+].[CH3:3][O:4][NH:5][S:6]([C:9]1[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][CH:10]=1)(=[O:8])=[O:7].F[C:17]1[CH:22]=[CH:21][C:20]([S:23][CH3:24])=[CH:19][C:18]=1[N+:25]([O-:27])=[O:26].ClC1C=CC(SC)=CC=1[N+]([O-])=O>CN(C=O)C.O>[CH3:3][O:4][N:5]([S:6]([C:9]1[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][CH:10]=1)(=[O:8])=[O:7])[C:17]1[CH:22]=[CH:21][C:20]([S:23][CH3:24])=[CH:19][C:18]=1[N+:25]([O-:27])=[O:26]

Participants

7

Reactant 4

HCID 24758Sodium hydrideHCID 709811-Chloro-4-(methylthio)-2-nitrobenzeneHCID 15008723HCID 15008723, compoundHCID 18509240HCID 18509240, compound

Product 1

HCID 18509210HCID 18509210, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a suspension of sodium hydride (60%, 0.33 g (8.17 mmol)) in DMF (10.0 ml), N-methoxy-p-toluenesulfonamide (1.63 g (8.17 mmol)) was added with stirring under cooling with ice. To the resulting mixture, after 15 minutes' stirring at room temperature, a 3:2 mixture of 2-fluoro-5-(methylthio)nitrobenzene and 2-chloro-5-(methylthio)nitrobenzene (1.39 g) was added. The mixture was stirred overnight at room temperature, poured into water and extracted with diethyl ether. The extract was washed with water, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography with ethyl acetate-hexane (1:6 to 1:4) as eluent. The eluted substance was recrystallized from ethyl acetate-hexane to give 0.60 g of the title compound as yellow crystals.

Workup

  1. additionwas added
  2. temperatureunder cooling with ice
  3. stirringTo the resulting mixture, after 15 minutes' stirring at room temperature
  4. additionwas added
  5. stirringThe mixture was stirred overnight at room temperature
  6. extractionextracted with diethyl ether
  7. washThe extract was washed with water
  8. dry with materialdried over anhydrous magnesium sulfate
  9. concentrationconcentrated under reduced pressure
  10. customThe eluted substance was recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-d185b7a61bcf427889e91252791b97f8
Source dataset
uspto-grants-2003_07
Patent number
US06586617B1

Reaction notes

Loading…