Pyridine, 2,6-dichloro-3-(chloromethyl)- → Phthalimide

HRID 2187193Notes

Reaction equation

HRID 2187193 reaction equation
[C:1]1(=[O:11])[NH:5][C:4](=[O:6])[C:3]2=[CH:7][CH:8]=[CH:9][CH:10]=[C:2]12.[K].ClC1C(CCl)=CC=C(Cl)N=1>CN(C=O)C>[C:1]1(=[O:11])[NH:5][C:4](=[O:6])[C:3]2=[CH:7][CH:8]=[CH:9][CH:10]=[C:2]12

Participants

4

Reactant 2

HCID 6451791Pyridine, 2,6-dichloro-3-(chloromethyl)-HCID 24194345Phthalimide potassium salt

Product 1

HCID 6809Phthalimide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
65 °C

Procedure

In 40 ml of DMF was suspended 3.9 g (0.021 mole) of potassium phthalimide followed by addition of 3.9 g (0.02 mole) of 2,6-dichloro-3-pyridylmethyl chloride and the mixture was stirred at 60-70° C. for 2 hours. The DMF was distilled off under reduced pressure and the residue was diluted with 50 ml of water and extracted with CHCl3 (50 ml×3). The extract was dried over MgSO4 and concentrated and the resulting precipitate was collected by filtration, washed with ether and dried to give 3.8 g of N-2,6-dichloro-3-pyridylmethyl)phthalimide as white prisms.

Workup

  1. distillationThe DMF was distilled off under reduced pressure
  2. additionthe residue was diluted with 50 ml of water
  3. extractionextracted with CHCl3 (50 ml×3)
  4. dry with materialThe extract was dried over MgSO4
  5. concentrationconcentrated
  6. filtrationthe resulting precipitate was collected by filtration
  7. washwashed with ether
  8. customdried

Sources & evidence

ORD record
ord-f96a20cdfc734714856e135f20e88ff3
Source dataset
uspto-grants-2002_06
Patent number
US06407248B1

Reaction notes

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