Iodine → HCID 21465560, compound

HRID 1939998Notes

Reaction equation

HRID 1939998 reaction equation
CN(C)[CH:3]=[CH:4][C:5]([C:7]1[C:12]([O:13][CH3:14])=[CH:11][C:10]([O:15][CH3:16])=[CH:9][C:8]=1[OH:17])=[O:6].CO.[I:21]I.S([O-])([O-])(=O)=S.[Na+].[Na+]>C(Cl)Cl>[CH3:14][O:13][C:12]1[CH:11]=[C:10]([O:15][CH3:16])[CH:9]=[C:8]2[C:7]=1[C:5](=[O:6])[C:4]([I:21])=[CH:3][O:17]2

Participants

6

Reactant 4

HCID 807Iodine2×HCID 887MethanolHCID 24477Sodium ThiosulfateHCID 53853428HCID 53853428, compound

Product 1

HCID 21465560HCID 21465560, compoundYield 51.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
80 °C

Procedure

To an eggplant type flask (500 ml), 3-dimethylamino-4',6'-dimethoxy-2'-hydroxyacrylophenone (5.026 g) prepared in Example 15 and methyl alcohol (200 ml) were added. The mixture was dissolvedby heating at 80° C. for 10 minutes with stirring. After the solution was cooled, iodine (10.152 g) was slowly added. After 15 minutes, the disappearance of the starting material was confirmed by thin layer chromatography. To the reaction mixture, methylene chloride (700 ml) and then 5% aqueous solution of sodium thiosulfate (200 ml) were added to reduce iodine. The organic layer was separated, and washed with distilled water (100 ml). The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The crude product was separated and purified by silica gel column chromatography (n-hexane/ethyl acetate=2/1 to 1/2), and recrystallized from ether to give the titled compound (3.43 g; yield=34.5%) as colorless crystals. Melting point: 158°-160° C. 1H-NMR(CDCl3, δ ppm): 3.88 (s, 3H, OMe), 3.93 (s, 3H, OMe), 6.38 (s, 1H, ArH), 6.42 (s, 1H, ArH), 8.06 (s, 1H, H2).

Workup

  1. dissolutionThe mixture was dissolvedby
  2. temperatureAfter the solution was cooled
  3. customThe organic layer was separated
  4. washwashed with distilled water (100 ml)
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe crude product was separated
  8. custompurified by silica gel column chromatography (n-hexane/ethyl acetate=2/1 to 1/2)
  9. customrecrystallized from ether

Sources & evidence

ORD record
ord-640ee52c75b24100890ad9d05723db7b
Source dataset
uspto-grants-1997_12
Patent number
US05698575

Reaction notes

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