Cesium carbonate → HCID 540203, compound

HRID 2197998Notes

Reaction equation

HRID 2197998 reaction equation
Cl[C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].[C:12]([NH:15][C:16]1[CH:21]=[CH:20][C:19]([SH:22])=[CH:18][CH:17]=1)(=[O:14])[CH3:13].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C.C(OCC)(=O)C>[Cl:8][C:6]1[CH:5]=[CH:4][C:3]([N+:9]([O-:11])=[O:10])=[C:2]([S:22][C:19]2[CH:18]=[CH:17][C:16]([NH:15][C:12](=[O:14])[CH3:13])=[CH:21][CH:20]=2)[CH:7]=1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 118992,4-DichloronitrobenzeneHCID 707774'-Mercaptoacetanilide

Product 1

HCID 540203HCID 540203, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 2,4-Dichloro nitro benzene (0.25 g, 1.3 mmol), 4-Acetamido thiophenol (0.26 g, 1.43 mmol) and cesium carbonate (0.466 g, 1.43 mmol) in DMF (3 mL) was heated 2.5 hr at 100° C. The mixture was cooled, diluted with ethyl acetate (100 mL) and the organic layer was washed with water and aqueous 10% sodium chloride solution, then, dried over anhydrous sodium sulfate. The drying agent was filtered and the solvent removed under vacuum. The residue is purified by silica gel column chromatography eluting with CH2Cl2/methanol leaving the title compound as a yellow solid (0.25 g, 63%).

Workup

  1. temperatureThe mixture was cooled
  2. washthe organic layer was washed with water and aqueous 10% sodium chloride solution
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationThe drying agent was filtered
  5. customthe solvent removed under vacuum
  6. customThe residue is purified by silica gel column chromatography
  7. washeluting with CH2Cl2/methanol leaving the title compound as a yellow solid (0.25 g, 63%)

Sources & evidence

ORD record
ord-f2d33a01339f42fd9ee399ca7abcd652
Source dataset
uspto-grants-2012_12
Patent number
US08338605B2

Reaction notes

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