Iodine → 6-Iodo-4'-methylaminoflavone

HRID 215669ノート

反応式

HRID 215669 の反応式
[I:1]I.C([Sn](CCCC)(CCCC)[C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][CH:17]=1)[O:14][C:13]([C:18]1[CH:23]=[CH:22][C:21]([NH:24][CH3:25])=[CH:20][CH:19]=1)=[CH:12][C:11]2=[O:26])CCC.S(=O)(O)[O-].[Na+]>C(Cl)(Cl)Cl>[I:1][C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][CH:17]=1)[O:14][C:13]([C:18]1[CH:23]=[CH:22][C:21]([NH:24][CH3:25])=[CH:20][CH:19]=1)=[CH:12][C:11]2=[O:26]

参加物

5

反応物 3

HCID 807IodineHCID 11613563HCID 11613563、化合物HCID 23665763Sodium Bisulfite

生成物 1

HCID 116322426-Iodo-4'-methylaminoflavone

試薬・触媒・溶媒 1

HCID 6212Chloroform溶媒2 回

実験手順

A chloroform solution of iodine (1.5 ml, 1 M) was added to a chloroform solution (20 ml) that contained compound 8 (100 mg, 0.185 mmol) at room temperature. The obtained mixture was reacted at room temperature for 10 minutes, and a saturated sodium bisulfite aqueous solution (15 ml) was then added thereto, so as to terminate the reaction. The chloroform layer was separated, and it was then dried over sodium sulfate. Thereafter, the solvent was distilled away under reduced pressure, and the residue was then subjected to silica gel column chromatography using ethyl acetate/hexane (1/2) as an elution solvent, so as to obtain a product of interest, 6-iodo-4′-methylaminoflavone (compound 10). Yield: 20 mg (yield constant: 28.7%) 1H NMR (300 MHz, CDCl3) δ8.53 (s, 1H), 7.90 (d, J=9.0 Hz, 1H), 7.75 (d, J=8.4 Hz, 2H), 7.28 (d, J=10.8 Hz, 1H), 6.64-6.69 (m, 3H), 4.15 (s, 1H), 2.93 (s, 3H). MS m/z 377 (M+).

後処理

  1. customat room temperature
  2. customThe obtained mixture was reacted at room temperature for 10 minutes
  3. customso as to terminate
  4. customthe reaction
  5. customThe chloroform layer was separated
  6. dry with materialit was then dried over sodium sulfate
  7. distillationThereafter, the solvent was distilled away under reduced pressure

出典と根拠

ORDレコード
ord-7b4ea587df7d4e989b4921161f990e8e
出典データセット
uspto-grants-2012_06
特許番号
US08192717B2

反応ノート

読み込み中…