1,4-Dioxane → HCID 58361485, compound

HRID 2076451Notes

Reaction equation

HRID 2076451 reaction equation
[C:1]1([S:7]([O:10][C:11]2[C:20]([Br:21])=[C:19]3[C:14]([CH:15]=[CH:16][C:17]([CH3:22])=[N:18]3)=[CH:13][CH:12]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[O:23]1CCOCC1>>[C:1]1([S:7]([O:10][C:11]2[C:20]([Br:21])=[C:19]3[C:14]([CH:15]=[CH:16][C:17]([CH:22]=[O:23])=[N:18]3)=[CH:13][CH:12]=2)(=[O:9])=[O:8])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

3

Reactant 2

HCID 312751,4-Dioxane2×HCID 58361490HCID 58361490, compound

Product 1

HCID 58361485HCID 58361485, compoundYield 91%

Conditions

Temperature
80 °C

Procedure

A mixture of SeO2 (500 mg, 4.51 mmol) and 1,4-dioxane (10 mL) was heated to over 80° C. 8-Bromo-2-methylquinolin-7-yl benzenesulfonate (15, 1.70 g, 4.49 mmol) in 1,4-dioxane (5 mL) was added. After stirring at 80° C. for 24 h, the reaction was cooled and vacuum filtered. The filtrate was collected and concentrated to yield a yellow solid. Purification by SiO2 column chromatography (CHCl3) gave 16 as a white solid (1.60 g, 4.08 mmol, 91% yield). 1H NMR (500 MHz, CDCl3) δ 10.25 (s, 1H), 8.37 (d, 1H, J=7.5 Hz), 8.09 (d, 1H, J=8.5 Hz), 7.99 (d, 2H, J=7.0 Hz), 7.91 (d, 1H, J=9.0 Hz), 7.79 (d, 1H, J=9.0 Hz), 7.72 (t, 1H, J=7.5 Hz), 7.57 (t, 2H, J=8.0 Hz). 13C NMR (500 MHz, CDCl3) δ 193.33, 153.80, 149.08, 146.10, 138.35, 135.82, 135.17, 129.79, 129.66, 128.99, 128.37, 125.61, 119.93, 118.51.

Workup

  1. temperaturethe reaction was cooled
  2. filtrationvacuum filtered
  3. customThe filtrate was collected
  4. concentrationconcentrated
  5. customto yield a yellow solid
  6. customPurification by SiO2 column chromatography (CHCl3)

Sources & evidence

ORD record
ord-1fe583138f424f09823af60208862d57
Source dataset
uspto-grants-2011_04
Patent number
US07923562B2

Reaction notes

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