Cesium carbonate → Thioacetic Acid S-(5-Chloro-2-methoxy-benzyl)ester

HRID 11668Notes

Reaction equation

HRID 11668 reaction equation
C(=O)([O-])[O-].[Cs+].[Cs+].[C:7]([OH:10])(=[S:9])[CH3:8].[Cl:11][C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[C:14]([CH2:20]Cl)[CH:13]=1>CN(C)C=O.C(OCC)(=O)C>[Cl:11][C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[C:14]([CH:13]=1)[CH2:20][S:9][C:7](=[O:10])[CH3:8]

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 69467534-Chloro-2-(chloromethyl)-1-methoxybenzeneHCID 178418634HCID 178418634, compound

Product 1

HCID 85826700Thioacetic Acid S-(5-Chloro-2-methoxy-benzyl)esterYield 96%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of cesium carbonate (0.55 g, 1.70 mmol) in dimethylformamide (13 mL) was added thioacetic acid (0.24 g, 3.14 mmol) followed by addition of 4-chloro-2-chloromethyl-1-methoxybenzene (0.50 g, 2.62 mmol) in one portion. The reaction was stirred in the dark at ambient temperature overnight. The reaction was diluted with ethyl acetate, washed with water, 5% aqueous sodium hydrogen carbonate, and brine. The organic layer was separated, dried over sodium sulfate, filtered and concentrated in vacuo. Chromatography on silica gel gave the title compound (0.58 g).

Workup

  1. washwashed with water, 5% aqueous sodium hydrogen carbonate, and brine
  2. customThe organic layer was separated
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9080e5381cc74e3c8ad204cd6fbe546f
Source dataset
uspto-grants-2006_08
Patent number
US07098212B2

Reaction notes

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