Sodium Azide → 4-Azido-5-chloropyridine-3-carbaldehyde

HRID 626705노트

반응식

HRID 626705 반응식
Cl[C:2]1[C:7]([Cl:8])=[CH:6][N:5]=[CH:4][C:3]=1[CH:9]=[O:10].[N-:11]=[N+:12]=[N-:13].[Na+]>CN(C=O)C>[N:11]([C:2]1[C:7]([Cl:8])=[CH:6][N:5]=[CH:4][C:3]=1[CH:9]=[O:10])=[N+:12]=[N-:13]

참가 물질

4

반응물 2

HCID 33557Sodium AzideHCID 595965804,5-Dichloropyridine-3-carbaldehyde

생성물 1

HCID 866970494-Azido-5-chloropyridine-3-carbaldehyde수율 96%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

A mixture of 4,5-dichloropyridine-3-carbaldehyde (6.78 g, 38.5 mmol) and sodium azide (2.62 g, 40.4 mmol) in DMF (25 mL) was stirred at room temperature for 18 hours. The reaction mixture was quenched with brine (250 mL) and extracted with ethyl acetate (3×100 mL). The combined organic extracts were dried over anhydrous sodium sulphate and concentrated under reduced pressure. The residue was purified by silica gel flash chromatography (0-40% ethyl acetate in pentane) to afford the title compound as a yellow solid (6.7 g, 96% yield). 1H NMR (400 MHz, CDCl3): δ 10.36 (s, 1H), 8.84 (s, 1H), 8.65 (s, 1H).

후처리

  1. customThe reaction mixture was quenched with brine (250 mL)
  2. extractionextracted with ethyl acetate (3×100 mL)
  3. dry with materialThe combined organic extracts were dried over anhydrous sodium sulphate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel flash chromatography (0-40% ethyl acetate in pentane)

출처 및 근거

ORD 기록
ord-6bfcfd0dc6364ef3a2a4de86f0e0f2bc
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09309240B2

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