Water → 2-Iodo-6-nitrobenzonitrile

HRID 471599ノート

反応式

HRID 471599 の反応式
N[C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([N+:10]([O-:12])=[O:11])[C:3]=1[C:4]#[N:5].N([O-])=O.[Na+].[I-:17].[K+].O>OS(O)(=O)=O.C(O)(=O)C>[I:17][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([N+:10]([O-:12])=[O:11])[C:3]=1[C:4]#[N:5]

参加物

7

反応物 4

HCID 962WaterHCID 4875Potassium IodideHCID 127157292-Amino-6-nitrobenzonitrileHCID 23668193Sodium Nitrite

生成物 1

HCID 249719892-Iodo-6-nitrobenzonitrile収率 53.2%

試薬・触媒・溶媒 2

HCID 176Acetic Acid溶媒HCID 1118Sulfuric Acid溶媒2 回

反応条件

温度
45 °C

実験手順

2-Amino-6-nitrobenzonitrile (Example 130e) (4.32 g, 26.5 mmol) was added in small portions to a suspension of sodium nitrite (2.19 g, 31.7 mmol) in concentrated H2SO4 (43 mL) and acetic acid (43 mL) at 45° C. The reaction was heated at 45° C. for 1 h and then added in small portions to a solution of potassium iodide (7.47 g, 45.0 mmol) in H2SO4 (1 M, 43 mL). After stirring at room temperature for 1.5 h, iced water was added to the reaction and the precipitated product was collected by filtration. The product was purified by chromatography on silica gel eluting with CH2Cl2, to give 2-iodo-6-nitrobenzonitrile (3.86 g, 53%) as a yellow solid. 1H-NMR (400 MHz, DMSO-d6) δ 8.46-8.52 (m, 1H), 8.34-8.38 (m, 1H), 7.66-7.71 (m, 1H).

後処理

  1. filtrationthe precipitated product was collected by filtration
  2. customThe product was purified by chromatography on silica gel eluting with CH2Cl2

出典と根拠

ORDレコード
ord-f6993b24176940b6961d30d7901e21a7
出典データセット
uspto-grants-2014_01
特許番号
US08633186B2

反応ノート

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