Water → 2,2-Difluoro-2-(2-pyridyl)ethylazide

HRID 1281899ノート

反応式

HRID 1281899 の反応式
FC(F)(F)S(O[CH2:7][C:8]([F:16])([F:15])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=1)(=O)=O.[N-:19]=[N+:20]=[N-:21].[Na+].O>CN(C=O)C>[F:15][C:8]([F:16])([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=1)[CH2:7][N:19]=[N+:20]=[N-:21]

参加物

5

反応物 3

HCID 962WaterHCID 33557Sodium AzideHCID 110662242,2-Difluoro-2-(2-pyridyl)ethyl trifluoromethanesulfonate

生成物 1

HCID 118054052,2-Difluoro-2-(2-pyridyl)ethylazide

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
60 °C

実験手順

To a stirred solution of 5.5 g of 2,2-difluoro-2-(2-pyridyl)ethyl trifluoromethanesulfonate 1-4 in 70 mL of DMF was added 6.74 g (104 mmol) of sodium azide under Ar. The mixture was heated to 60° C. overnight. A second batch was run in the same manner, and after cooling to rt, both reactions were poured into 600 mL of water, and extracted with 3×500 mL of ether. The combined extracts were washed with brine, dried over Na2SO4 and concentrated at reduced pressure to give an oil that was purified by SiO2 (10×6 cm) using hexane 1:3 EtOAc-hexane and 1:1 EtOAc-hexane. The product-containing fractions were concentrated at reduced pressure to give 1-5 as a yellow oil: 1H NMR (CDCl3) δ 4.05 (t, 2H), 7.4-7.45 (m, 1H), 7.73 (d, 1H), 7.83-7.89 (m, 1H), 8.67 (d, 1H).

後処理

  1. temperatureafter cooling to rt
  2. extractionextracted with 3×500 mL of ether
  3. washThe combined extracts were washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated at reduced pressure
  6. customto give an oil that
  7. customwas purified by SiO2 (10×6 cm)
  8. concentrationThe product-containing fractions were concentrated at reduced pressure

出典と根拠

ORDレコード
ord-54061f5dce3b46ceb9f9191378d928d0
出典データセット
uspto-grants-2002_09
特許番号
US06455532B1

反応ノート

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