Iodine → 6-Iodo-4'-methylaminoflavone

HRID 215669노트

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HRID 215669 반응식
[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]

참가 물질

5

반응물 3

HCID 807IodineHCID 11613563HCID 11613563, 화합물HCID 23665763Sodium Bisulfite

생성물 1

HCID 116322426-Iodo-4'-methylaminoflavone

시약·촉매·용매 1

HCID 6212Chloroform용매2회

실험 절차

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+).

후처리

  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

출처 및 근거

ORD 기록
ord-7b4ea587df7d4e989b4921161f990e8e
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08192717B2

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