Dimethylformamide → HCID 86602521, compound

HRID 30684Notes

Reaction equation

HRID 30684 reaction equation
Br[CH2:2][C:3]1[CH:17]=[CH:16][CH:15]=[CH:14][C:4]=1[CH2:5][P:6](=[O:13])([O:10][CH2:11][CH3:12])[O:7][CH2:8][CH3:9].[C:18]1(=[O:28])[NH:22][C:21](=[O:23])[C:20]2=[CH:24][CH:25]=[CH:26][CH:27]=[C:19]12.[K].CN(C)C=O>O>[O:23]=[C:21]1[C:20]2[C:19](=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:18](=[O:28])[N:22]1[CH2:2][C:3]1[CH:17]=[CH:16][CH:15]=[CH:14][C:4]=1[CH2:5][P:6](=[O:13])([O:10][CH2:11][CH3:12])[O:7][CH2:8][CH3:9]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 151719952-(Diethylphosphonomethyl)benzyl bromideHCID 24194345Phthalimide potassium salt

Product 1

HCID 86602521HCID 86602521, compoundYield 84.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of diethyl [2-(bromomethyl)benzyl]phosphonate (11.2 g), potassium phthalimide (6.46 g) and N,N-dimethylformamide (100 ml) was stirred at room temperature for 14 hrs. The reaction mixture was poured into water, and the mixture was extracted with ethyl acetate. The organic layer was ashed with water, dried over anhydrous magnesium sulfate, and concentrated. Recrystallization of the residue from ethyl acetate-hexane gave diethyl {2-[(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)methyl]benzyl}phosphonate (11.3 g, 83%) as colorless prism crystals. melting point: 91-92° C.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationconcentrated
  4. customRecrystallization of the residue from ethyl acetate-hexane

Sources & evidence

ORD record
ord-0164f956a36a4202a26f3ae97f3d202d
Source dataset
uspto-grants-2008_09
Patent number
US07423159B2

Reaction notes

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