Water → 2-Iodo-6-nitrobenzonitrile

HRID 711736노트

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HRID 711736 반응식
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]

참가 물질

7

반응물 4

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

생성물 1

HCID 249719892-Iodo-6-nitrobenzonitrile수율 53.2%

시약·촉매·용매 2

HCID 176Acetic Acid용매HCID 1118Sulfuric Acid용매2회

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온도
45 °C

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-bcb1027035014acbbfc8d9bfac44d08f
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09181276B2

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