Sodium Azide → 2-Azido-4-nitrobenzyl alcohol

HRID 650512Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 650512
[NH2:1][C:2]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[CH:7]=[CH:6][C:3]=1[CH2:4][OH:5].N([O-])=O.[Na+].C([O-])(=O)C.[Na+].[N-:22]=[N+:23]=[N-].[Na+]>Cl.O.O>[N:1]([C:2]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[CH:7]=[CH:6][C:3]=1[CH2:4][OH:5])=[N+:22]=[N-:23]

Komponenten

7

Edukt 4

HCID 33557Sodium AzideHCID 541982-Amino-4-nitrobenzyl alcoholHCID 517045Sodium AcetateHCID 23668193Sodium Nitrite

Produkt 1

HCID 867572472-Azido-4-nitrobenzyl alcoholAusbeute 78 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittel2×HCID 21885828Hydrate;hydrochlorideLösungsmittel

Versuchsvorschrift

To a suspension of 2-amino-4-nitrobenzyl alcohol [(0.5 g) Bio. Org. Med. Chem (1995) 3, 2, 129] in concentrated hydrochloric acid/H2O (15 ml of 1:1 v:v) at −50 to 0° was added a solution of sodium nitrite (0.24 g) in water (2.5 ml) dropwise so the temperature did not rise above 0°. The mixture was stirred for 10 min, and added dropwise to a cooled (0°) solution of sodium acetate (3.0 g) and sodium azide (0.2 g) in water (10 ml). The resulting solid was filtered, washed with water and dried on the sinter to give the title compound as a pale brown powder (0.45 g, 78%). δH (d6 DMSO): 4.51 (2H, s), 5.52 (1H, br), 7.72 (1H, d, J 8.4 Hz), 7.99 (1H, d, J 2.2 Hz) and 8.04 (1H, dd, J 2.2, 8.4 Hz) .

Aufarbeitung

  1. customdid not rise above 0°
  2. additionadded dropwise to
  3. filtrationThe resulting solid was filtered
  4. washwashed with water
  5. customdried on the sinter

Quellen und Nachweise

ORD-Eintrag
ord-880195bf9f2d4183924f5a97064d83a8
Quelldatensatz
uspto-grants-2001_08
Patentnummer
US06274577B1

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