Sodium Azide → 2-Phthalimidophenyl azide

HRID 859156

반응식

HRID 859156 반응식
[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]

참가 물질

6

반응물 3

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

생성물 1

HCID 234995172-Phthalimidophenyl azide수율 94.1%

시약·촉매·용매 2

HCID 176Acetic Acid용매HCID 962Water용매3회

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-98b43f9de2bb48838c56a68050b6a42c
출처 데이터셋
uspto-grants-2006_12
특허 번호
US07151112B1

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