Cesium carbonate → HCID 54003165, compound

HRID 1369292Notes

Reaction equation

HRID 1369292 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]([S:14][CH2:15][CH2:16][CH2:17]Cl)[C:7]([OH:13])=[C:8]([CH:12]=1)[C:9]([NH2:11])=[O:10])(=[O:3])[CH3:2].C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C.C(OCC)(=O)C.Cl>[C:1]([C:4]1[CH:12]=[C:8]([C:9]([NH2:11])=[O:10])[C:7]2[O:13][CH2:17][CH2:16][CH2:15][S:14][C:6]=2[CH:5]=1)(=[O:3])[CH3:2]

Participants

6

Reactant 2

HCID 10796Cesium carbonateHCID 18519021HCID 18519021, compound

Product 1

HCID 54003165HCID 54003165, compoundYield 40%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

The 5-acetyl-3-(3-chloro-propylsulfanyl)-2-hydroxy-benzamide (2.87 g, 10 mmol) was dissolved in 8 mL dry DMF. Solid Cs2CO3 (4.93 g, 15.1 mmol) was added, followed by catalytic amounts of KI (0.1 g). The suspension was warmed to 70° C. under nitrogen and was stirred for 72 h. After cooling, it was diluted with ethyl acetate and enough 4 N HCl to make the pH about 2. The aqueous layer was extracted with more ethyl acetate. The combined organic layers were washed with water and brine. Drying over Na2SO4 and concentration yielded the product as a solid (1 g, 40%).

Workup

  1. temperatureAfter cooling
  2. extractionThe aqueous layer was extracted with more ethyl acetate
  3. washThe combined organic layers were washed with water and brine
  4. dry with materialDrying over Na2SO4 and concentration

Sources & evidence

ORD record
ord-72baf9e766874a8b9efa347ba0790263
Source dataset
uspto-grants-2003_06
Patent number
US06576766B1

Reaction notes

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