Sodium Azide → 2-Phthalimidophenyl azide

HRID 1836430

Reaction equation

HRID 1836430 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:16](=[O:17])[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]1=[O:18].N([O-])=O.[Na+].[N-:23]=[N+:24]=[N-].[Na+]>C(O)(=O)C.O>[N:1]([C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:9](=[O:18])[C:10]2[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:16]1=[O:17])=[N+:23]=[N-:24]

Participants

6

Reactant 3

HCID 33557Sodium AzideHCID 6736762-(2-Aminophenyl)isoindole-1,3-dioneHCID 23668193Sodium Nitrite

Product 1

HCID 234995172-Phthalimidophenyl azideYield 94.1%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent3×

Procedure

To a suspension of the 2-(2-aminophenyl)isoindole-1,3-dione (360 mg, 1.5 mmol) in acetic acid (20 mL) and water (4 mL) was added dropwise a solution of sodium nitrite (98 mg, 1.42 mmol) in water (2 mL). The mixture was allowed to stir for 10 minutes and then sodium azide (98 mg, 1.51 mmol) was added. The reaction mixture was stirred for 15 minutes before it was poured into water and was extracted with dichloromethane (3×50 mL). The extracts were washed with water and brine and dried over magnesium sulfate. Filtration and concentration in vacuo gave 373 mg (94%) of 2-(2-azidophenyl)isoindole-1,3-dione as a solid: 1H NMR (300 MHz, DMSO-d6) δ 7.94 (m, 4H), 7.58 (m, 1H), 7.48 (m, 2H), 7.32 (m, 1H).

Workup

  1. stirringThe reaction mixture was stirred for 15 minutes before it
  2. extractionwas extracted with dichloromethane (3×50 mL)
  3. washThe extracts were washed with water and brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationFiltration and concentration in vacuo

Sources & evidence

ORD record
ord-d314b9f4286845858dcb5334a50af38a
Source dataset
uspto-grants-2004_08
Patent number
US06777432B1

Linked notes

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