Iodine → 2-[4-(Dimethylamino)phenyl]-6-iodo-4H-1-benzopyran-4-one

HRID 215670Notes

Reaction equation

HRID 215670 reaction equation
[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]([N:24]([CH3:26])[CH3:25])=[CH:20][CH:19]=1)=[CH:12][C:11]2=[O:27])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]([N:24]([CH3:26])[CH3:25])=[CH:20][CH:19]=1)=[CH:12][C:11]2=[O:27]

Participants

5

Reactant 3

HCID 807IodineHCID 11570311HCID 11570311, compoundHCID 23665763Sodium Bisulfite

Product 1

HCID 115746592-[4-(Dimethylamino)phenyl]-6-iodo-4H-1-benzopyran-4-one

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

A chloroform solution of iodine (1 ml, 1 M) was added to a chloroform solution (5 ml) that contained compound 9 (30 mg, 0.054 mmol) at room temperature. The obtained mixture was reacted at room temperature for 30 minutes, and a saturated sodium bisulfite aqueous solution (5 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 (1/9) as an elution solvent, so as to obtain a product of interest, 6-iodo-4′-dimethylaminoflavone (compound 11). Yield: 10 mg (yield constant: 47.3%) 1H NMR (300 MHz, CDCl3) δ8.54 (s, 1H), 7.92 (d, J=9.0 Hz, 1H), 7.81 (d, J=9.0 Hz, 2H), 7.29 (d, J=9.0 Hz, 1H), 6.71-6.80 (m, 3H), 3.09 (s, 6H). MS m/z 392 (MH+).

Workup

  1. customat room temperature
  2. customThe obtained mixture was reacted at room temperature for 30 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

Sources & evidence

ORD record
ord-4cc3a8d306b54112b67df2218e15704c
Source dataset
uspto-grants-2012_06
Patent number
US08192717B2

Reaction notes

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