Sodium Azide → 2-Phthalimidophenyl azide

HRID 1836430

Reaktionsgleichung

Reaktionsgleichung von HRID 1836430
[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]

Komponenten

6

Edukt 3

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

Produkt 1

HCID 234995172-Phthalimidophenyl azideAusbeute 94,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittelHCID 962WaterLösungsmittel3×

Versuchsvorschrift

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).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-d314b9f4286845858dcb5334a50af38a
Quelldatensatz
uspto-grants-2004_08
Patentnummer
US06777432B1

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