Methyl iodide → HCID 21041641, compound

HRID 10719Notes

Reaction equation

HRID 10719 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5](/[CH:16]=[CH:17]/[C:18]([C:20]2[CH:25]=[CH:24][C:23]([NH:26][S:27]([CH3:30])(=[O:29])=[O:28])=[CH:22][CH:21]=2)=[O:19])[CH:6]=[C:7]([C:11]2[S:12][CH:13]=[CH:14][CH:15]=2)[C:8]=1[O:9][CH3:10].[C:31](=O)([O-])[O-].[K+].[K+].CI>CN(C=O)C.O>[CH3:1][O:2][C:3]1[CH:4]=[C:5](/[CH:16]=[CH:17]/[C:18]([C:20]2[CH:25]=[CH:24][C:23]([N:26]([CH3:31])[S:27]([CH3:30])(=[O:28])=[O:29])=[CH:22][CH:21]=2)=[O:19])[CH:6]=[C:7]([C:11]2[S:12][CH:13]=[CH:14][CH:15]=2)[C:8]=1[O:9][CH3:10]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 21041640HCID 21041640, compound

Product 1

HCID 21041641HCID 21041641, compoundYield 45.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of N-{4-[3E-(3,4-dimethoxy-5-thiophen-2-yl-phenyl)-acryloyl]-phenyl}-methanesulfonamide (Ex-14, 90 mg, 0.20 mmol) in anhydrous DMF was treated with potassium carbonate (56.1 mg, 0.41). Methyl iodide (126.32 uL, 2.03 mmol) was added to the reaction mixture which was then refluxed for 1.5 hours under inert conditions. The reaction was diluted with water (25 mL) and extracted with diethyl ether (2×50 mL). The organic portion was dried over sodium sulfate, filtered, and concentrated to a yellow oil. The crude material was purified by silica gel chromatography (30–50% ethyl acetate/hexanes) to give 42 mg (45%) of the title compound as a yellow solid. 1H-NMR (CDCl3) δ 8.06 (d, 2H), 7.59 (d, 1H), 7.54 (m, 4H), 7.42 (m, 2H), 7.12 (m, 2H), 3.97 (s, 3H), 3.88 (s, 3H), 3.40 (s, 3H), 2.89 (s, 3H). MS m/z=457 ([M]+, 100%).

Workup

  1. temperaturewas then refluxed for 1.5 hours under inert conditions
  2. extractionextracted with diethyl ether (2×50 mL)
  3. dry with materialThe organic portion was dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated to a yellow oil
  6. customThe crude material was purified by silica gel chromatography (30–50% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-d20f8e28d4694cbc89f6276a2d3db565
Source dataset
uspto-grants-2006_08
Patent number
US07094801B2

Reaction notes

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