Sodium Azide → 2-Phthalimidophenyl azide

HRID 1836430

反応式

HRID 1836430 の反応式
[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]

参加物

6

反応物 3

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

生成物 1

HCID 234995172-Phthalimidophenyl azide収率 94.1%

試薬・触媒・溶媒 2

HCID 176Acetic Acid溶媒HCID 962Water溶媒3 回

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-d314b9f4286845858dcb5334a50af38a
出典データセット
uspto-grants-2004_08
特許番号
US06777432B1

関連ノート

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