1-Chloro-2,4-Dinitrobenzene → 2-(2,4-Dinitrophenoxy)-1H-isoindole-1,3(2H)-dione

HRID 513030Notes

Reaction equation

HRID 513030 reaction equation
[OH:1][N:2]1[C:10](=[O:11])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]1=[O:12].C(N(CC)CC)C.Cl[C:21]1[CH:26]=[CH:25][C:24]([N+:27]([O-:29])=[O:28])=[CH:23][C:22]=1[N+:30]([O-:32])=[O:31]>CC(C)=O>[N+:27]([C:24]1[CH:23]=[C:22]([N+:30]([O-:32])=[O:31])[CH:21]=[CH:26][C:25]=1[O:1][N:2]1[C:10](=[O:11])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]1=[O:12])([O-:29])=[O:28]

Participants

5

Reactant 3

HCID 61-Chloro-2,4-DinitrobenzeneHCID 8471TriethylamineHCID 10665N-Hydroxyphthalimide2×

Product 1

HCID 70363092-(2,4-Dinitrophenoxy)-1H-isoindole-1,3(2H)-dione

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A 1 L four-necked flask equipped with an overhead stirrer, thermocouple and a condenser was charged with 2-hydroxyisoindoline-1,3-dione (25 g, 153 mmol) and acetone (500 mL). To this stirred suspension was added triethylamine (15.7 g, 154 mmol). The reaction mixture turned dark red and 2-hydroxyisoindoline-1,3-dione slowly dissolved and became a homogeneous solution after 10 minutes. 1-Chloro-2,4-dinitrobenzene (31 g, 153 mmol) was added and the reaction was stirred at room temperature for 2 hours. After this time, a bright yellow suspension formed, and the reaction mixture was poured into 500 mL of ice-water. The precipitate was filtered and washed three times with cold MeOH (100 mL). The solid was compressed and washed with heptanes (3×100 mL) and dried under vacuum to give 2-(2,4-dinitrophenoxy)isoindoline-1,3-dione (I-33). 1H NMR (400 MHz, CDCl3) δ 8.99 (d, 1 H), 8.44 (dd, 1 H), 8.03-7.97 (m, 2 H), 7.95-7.90 (m, 2 H), 7.46 (d, 1 H).

Workup

  1. customA 1 L four-necked flask equipped with an overhead stirrer
  2. customafter 10 minutes
  3. customAfter this time, a bright yellow suspension formed
  4. filtrationThe precipitate was filtered
  5. washwashed three times with cold MeOH (100 mL)
  6. washwashed with heptanes (3×100 mL)
  7. customdried under vacuum

Sources & evidence

ORD record
ord-f521a5510a0f4eedb25887deff44b9c5
Source dataset
uspto-grants-2015_08
Patent number
US09102671B2

Reaction notes

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