HCID 21906257, compound → HCID 21906206, compound

HRID 1883056Notes

Reaction equation

HRID 1883056 reaction equation
[CH3:1][S:2][CH3:3].[Na].[Cl:5][C:6]1[CH:7]=[CH:8][C:9]([NH:12][C:13](=[O:24])[C:14]2[CH:19]=C(F)[CH:17]=[CH:16][C:15]=2[N+:21]([O-:23])=[O:22])=[N:10][CH:11]=1>CN(C)C=O>[Cl:5][C:6]1[CH:7]=[CH:8][C:9]([NH:12][C:13](=[O:24])[C:14]2[CH:19]=[C:1]([S:2][CH3:3])[CH:17]=[CH:16][C:15]=2[N+:21]([O-:23])=[O:22])=[N:10][CH:11]=1

Participants

4

Reactant 2

HCID 21906257HCID 21906257, compoundHCID 86593196Sodium methylsulfide

Product 1

HCID 21906206HCID 21906206, compoundYield 63.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a stirring solution of sodium methylsulfide (0.13 g, 2 mmol) in N,N-dimethylformamide (20 mL) was added N-(5-chloropyridin-2-yl)-5-fluoro-2-nitrobenzamide (0.48 g, 1.6 mmol) and additional N,N-dimethylformamide (5 mL). The reaction solution was stirred overnight at room temperature and concentrated in vacuo. The resulting residue was partitioned between dichloromethane and water and the layers separated. The organic phase was washed with saturated aqueous sodium bicarbonate, dried over magnesium sulfate, filtered, and concentrated in vacuo. The crude product was slurried in diethyl ether and filtered to give 0.33 g (63%) of a yellow solid.

Workup

  1. concentrationconcentrated in vacuo
  2. customThe resulting residue was partitioned between dichloromethane and water
  3. customthe layers separated
  4. washThe organic phase was washed with saturated aqueous sodium bicarbonate
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. filtrationfiltered

Sources & evidence

ORD record
ord-533714879c9848b1ad685abe71332f70
Source dataset
uspto-grants-2004_07
Patent number
US06759414B2

Reaction notes

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