Water → HCID 18455224, compound

HRID 547887Notes

Reaction equation

HRID 547887 reaction equation
[O:1]=[CH:2][C:3]1[CH:11]=[CH:10][C:8](O)=[C:5]([O:6][CH3:7])[CH:4]=1.C([O-])([O-])=O.[K+].[K+].CS([CH2:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][N:25]=1)(=O)=O.O>CN(C=O)C>[CH3:7][O:6][C:5]1[CH:4]=[C:3]([CH:11]=[CH:10][C:8]=1[CH2:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][N:25]=1)[CH:2]=[O:1]

Participants

6

Reactant 4

HCID 962WaterHCID 1183VanillinHCID 11430Potassium CarbonateHCID 22708771HCID 22708771, compound

Product 1

HCID 18455224HCID 18455224, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
75 °C

Procedure

Vanillin (2.5 mmol) is added to mixture of K2CO3 (12.5 mmol) and 2-(2-Methanesulfonyl-ethyl)-pyridine (1) (2.5 mmol) in DMF (0.2 M), and the resulting reaction mixture is heated to 75° C. for 16 h. After cooling to approximately room temperature, water is added and the aqueous mixture is extracted 5 times with methylene chloride. The methylene chloride layers are combined and concentrated to afford a residue, which is recrystallized in diethyl ether.

Workup

  1. customthe resulting reaction mixture
  2. temperatureAfter cooling to approximately room temperature
  3. extractionthe aqueous mixture is extracted 5 times with methylene chloride
  4. concentrationconcentrated
  5. customto afford a residue, which
  6. customis recrystallized in diethyl ether

Sources & evidence

ORD record
ord-f7123585ba5049978269d9374182cc24
Source dataset
uspto-grants-2011_05
Patent number
US07939657B2

Reaction notes

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