Potassium Carbonate → HCID 70053080, compound

HRID 583312Notes

Reaction equation

HRID 583312 reaction equation
[CH3:1][O:2][C:3](=[O:23])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([OH:10])[C:5]=1[NH:11][S:12]([C:15]1[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=1)(=[O:14])=[O:13].Cl.[N:25]1[CH:30]=[CH:29][CH:28]=[C:27]([CH2:31]Cl)[CH:26]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.O>[CH3:1][O:2][C:3](=[O:23])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([O:10][CH2:31][C:27]2[CH:26]=[N:25][CH:30]=[CH:29][CH:28]=2)[C:5]=1[N:11]([S:12]([C:15]1[CH:16]=[CH:17][C:18]([O:21][CH3:22])=[CH:19][CH:20]=1)(=[O:13])=[O:14])[CH2:31][C:27]1[CH:26]=[N:25][CH:30]=[CH:29][CH:28]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 233943-(Chloromethyl)pyridine hydrochlorideHCID 54048961HCID 54048961, compound

Product 1

HCID 70053080HCID 70053080, compoundYield 55.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 0.40 g (1.187 mmol) of the product of Example 31 dissolved in 5.0 mL of DMF was added 0.409 g (2.492 mmol) of 3-picolyl chloride hydrochloride and 1.03 g (7.477 mmol) of potassium carbonate. The reaction mixture was then stirred at room temperature for 18 h, diluted with water and extracted with ether. The organics were then extracted with 6N HCl solution and the aqueous acid layer was then basified with 6N NaOH solution and then extrrcted with ether. The resulting ether layer was dried over sodium sulfate, filtered and concentrated in vacuo to provide 0.34 g (55%) of the desired product as a brown oil. Electrospray Mass Spec: 520.2 (M+H)+

Workup

  1. extractionextracted with ether
  2. extractionThe organics were then extracted with 6N HCl solution
  3. dry with materialThe resulting ether layer was dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-06bf2eff5817459e98970c9d8d859e48
Source dataset
uspto-grants-1999_07
Patent number
US05929097

Reaction notes

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