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Iodine → HCID 86704621、化合物

HRID 1508571
ノート
印刷プレビュー

反応式

HRID 1508571 の反応式
N[C:2]1[CH:3]=[C:4]([C:9]2[C:10]([CH2:17][N:18]3[C@@H:22]([CH3:23])[C@@H:21]([C:24]4[CH:29]=[C:28]([C:30]([F:33])([F:32])[F:31])[CH:27]=[C:26]([C:34]([F:37])([F:36])[F:35])[CH:25]=4)[O:20][C:19]3=[O:38])=[N:11][C:12]([S:15][CH3:16])=[N:13][CH:14]=2)[CH:5]=[CH:6][C:7]=1[F:8].N(OCCCCC)=O.[I:47]I>C(Cl)(Cl)Cl.C(Cl)Cl>[F:35][C:34]([F:37])([F:36])[C:26]1[CH:25]=[C:24]([C@H:21]2[O:20][C:19](=[O:38])[N:18]([CH2:17][C:10]3[C:9]([C:4]4[CH:5]=[CH:6][C:7]([F:8])=[C:2]([I:47])[CH:3]=4)=[CH:14][N:13]=[C:12]([S:15][CH3:16])[N:11]=3)[C@H:22]2[CH3:23])[CH:29]=[C:28]([C:30]([F:33])([F:32])[F:31])[CH:27]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 807IodineHCID 10026Pentyl nitriteHCID 86704619HCID 86704619、化合物

生成物 1

HCID 86704621HCID 86704621、化合物

試薬・触媒・溶媒 2

HCID 6212Chloroform溶媒HCID 6344Dichloromethane溶媒

反応条件

温度
80 °C

実験手順

A mixture of the title compound from Step A (2.1 g, 3.75 mmol), n-pentyl nitrite (0.66 g, 5.62 mmol) and I2 (1.24 g, 4.87 mmol) in chloroform (20 mL) was stirred at 80° C. for 1 h. The mixture was cooled, and the solvent was diluted with CH2Cl2. The mixture was washed with Na2S2O3 (5 mL), and with brine (5 mL), dried (Na2SO4), filtered and the solvent was evaporated under reduced pressure. The residue was purified by column chromatography on silica gel Biotage 40M, eluting with EtOAc/hexane (10/90) to give the title compound as a yellow gum. 1H NMR (CDCl3, 500 MHz) δ 8.41 (s, 1H), 7.92 (s, 1H), 7.78 (s, 2H), 7.77 (m, 1H), 7.35 (m, 1H), 7.22 (m, 1H), 5.76 (d, J=8.5 Hz, 1H), 4.91 (d, J=17 Hz, 1H), 4.45 (m, 1H), 4.06 (d, J=17.5 Hz, 1H), 2.64 (s, 3H), 0.76 (d, J=7 Hz, 3H). LCMS=672.1 (M+H)+.

後処理

  1. temperatureThe mixture was cooled
  2. washThe mixture was washed with Na2S2O3 (5 mL)
  3. dry with materialwith brine (5 mL), dried (Na2SO4)
  4. filtrationfiltered
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue was purified by column chromatography on silica gel Biotage 40M
  7. washeluting with EtOAc/hexane (10/90)

出典と根拠

ORDレコード
ord-4124e88bc6ed4498a17fa3e80beefa65
出典データセット
uspto-grants-2015_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09221834B2

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート