Water → HCID 11644545, compound

HRID 1947109Notes

Reaction equation

HRID 1947109 reaction equation
[C:1]12[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=1)[NH:6][C:5](=[O:12])[O:4][C:2]2=[O:3].Cl.Cl[CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=1.[H-].[Na+].O>CN(C=O)C>[N:17]1[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=1[CH2:15][N:6]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:1]=2[C:2](=[O:3])[O:4][C:5]1=[O:12]

Participants

6

Reactant 4

HCID 962WaterHCID 8359Isatoic AnhydrideHCID 23392Picolyl chloride hydrochlorideHCID 24758Sodium hydride

Product 1

HCID 11644545HCID 11644545, compoundYield 34%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of isatoic anhydride (25.4 g, 0.156 mol) in DMF (300 mL) were added 2-(chloromethyl)pyridine hydrochloride (28.1 g, 0.171 mol) and sodium hydride (66% in oil, 12.5 g, 0.34 mol) under ice-cooling. The obtained mixture was stirred at room temperature for 42 hr. Water (750 mL) was added to the reaction mixture and the mixture was ice-cooled. The precipitated solid was collected by filtration, and recrystallized from acetone-diisopropyl ether to give the title compound (13.4 g, 34%).

Workup

  1. temperaturecooling
  2. temperaturecooled
  3. filtrationThe precipitated solid was collected by filtration
  4. customrecrystallized from acetone-diisopropyl ether

Sources & evidence

ORD record
ord-7b56b49d1b4f4ddea7a956785faae312
Source dataset
uspto-grants-2013_03
Patent number
US08399449B2

Reaction notes

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