Sodium Azide → 2-Azido-4-nitrobenzyl alcohol

HRID 650512

반응식

HRID 650512 반응식
[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]

참가 물질

7

반응물 4

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

생성물 1

HCID 867572472-Azido-4-nitrobenzyl alcohol수율 78%

시약·촉매·용매 2

HCID 962Water용매2회HCID 21885828Hydrate;hydrochloride용매

실험 절차

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) .

후처리

  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

출처 및 근거

ORD 기록
ord-880195bf9f2d4183924f5a97064d83a8
출처 데이터셋
uspto-grants-2001_08
특허 번호
US06274577B1

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