Potassium Carbonate → HCID 18998887, compound

HRID 2260711Notes

Reaction equation

HRID 2260711 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:14][CH3:15])=[C:6]([CH:13]=1)[C:7]([NH:9][CH2:10][CH2:11][OH:12])=[O:8].C(=O)([O-])[O-].[K+].[K+].F[C:23]1[CH:30]=[CH:29][C:26]([CH:27]=[O:28])=[CH:25][CH:24]=1>CS(C)=O.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:14][CH3:15])=[C:6]([CH:13]=1)[C:7]([NH:9][CH2:10][CH2:11][O:12][C:23]1[CH:30]=[CH:29][C:26]([CH:27]=[O:28])=[CH:25][CH:24]=1)=[O:8]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 680234-FluorobenzaldehydeHCID 9497550HCID 9497550, compound

Product 1

HCID 18998887HCID 18998887, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

A mixture of 2-(N-(5-chloro-2-methoxybenzoyl)amino)ethanol (4.5 g), potassium carbonate (5 g) and 4-fluorobenzaldehyde (2.5 g, 2.16 ml) were heated at 100° C. in dry dimethylsulphoxide (50 ml) for 18 hours. The mixture was cooled, diluted with water and extracted with diethyl ether containing a little methanol. The organic layers were combined, dried (MgSO4) and evaporated. The residual oil was chromatographed on silica gel with 2% methanol in dichloromethane as solvent to afford the title compound as an oil.

Workup

  1. temperatureThe mixture was cooled
  2. extractionextracted with diethyl ether containing a little methanol
  3. dry with materialdried (MgSO4)
  4. customevaporated
  5. customThe residual oil was chromatographed on silica gel with 2% methanol in dichloromethane as solvent

Sources & evidence

ORD record
ord-f05ce85363c245d59f84176d5121f775
Source dataset
uspto-grants-1995_12
Patent number
US05478851

Reaction notes

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