Benzene, 1-(chloromethyl)-3,5-dinitro- → (1H)Isoindole-1,3(2H)-dione, 2-[(3,5-dinitrophenyl)methyl]-

HRID 431377Notes

Reaction equation

HRID 431377 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:9]=[C:10]([N+:12]([O-:14])=[O:13])[CH:11]=1)[CH2:7]Cl)([O-:3])=[O:2].[C:15]1(=[O:25])[NH:19][C:18](=[O:20])[C:17]2=[CH:21][CH:22]=[CH:23][CH:24]=[C:16]12.[K]>CC(N(C)C)=O>[N+:1]([C:4]1[CH:5]=[C:6]([CH2:7][N:19]2[C:15](=[O:25])[C:16]3[C:17](=[CH:21][CH:22]=[CH:23][CH:24]=3)[C:18]2=[O:20])[CH:9]=[C:10]([N+:12]([O-:14])=[O:13])[CH:11]=1)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 94673Benzene, 1-(chloromethyl)-3,5-dinitro-HCID 24194345Phthalimide potassium salt

Product 1

HCID 628240(1H)Isoindole-1,3(2H)-dione, 2-[(3,5-dinitrophenyl)methyl]-

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

A solution of 3,5-dinitrobenzyl chloride (2.2 g, 10 mmol) in DMA (40 mL) was treated with potassium phthalimide (1.9 g, 10 mmol) and the mixture stirred 12 h. The mixture was then concentrated and the solid residue washed with ethyl acetate, dried, washed with water and dried to give 2.5 g (76%) of essentially pure adduct as a white solid: 1H NMR 400 MHz (DMSO) δ5.06 (s, 2H); 7.82-7.97 (m, 4H); 8.62 (s, 2H); 8.74 (s, 1H).

Workup

  1. concentrationThe mixture was then concentrated
  2. washthe solid residue washed with ethyl acetate
  3. customdried
  4. washwashed with water
  5. customdried
  6. customto give 2.5 g (76%) of essentially pure adduct as a white solid

Sources & evidence

ORD record
ord-3974f20f254948c09871d7bf131e0640
Source dataset
uspto-grants-2003_12
Patent number
US06656971B2

Reaction notes

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