1,4-Dioxane → HCID 58361485, compound

HRID 2076447Notes

Reaction equation

HRID 2076447 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 (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, leaving a yellow solid. Purification by silica gel with CHCl3 (100%) gave SO186 as a white solid (1.60 g, 4.08 mmol, 91% yield). 13CNMR (ppm, 500 MHz, CDCl3, 298 K) δ: 193.330, 153.804, 149.083, 146.098, 138.351, 135.815, 135.165, 129.787, 129.663, 128.990, 128.365, 125.611, 119.933, 118.514. 1HNMR (ppm, 500 MHz, CDCl3, 298 K) δ: 10.247 (s, 1H), 8.365 (d, 1H, J=7.5 Hz), 8.090 (d, 1H, J=8.5 Hz), 7.986 (d, 2H, J=7.0 Hz), 7.913 (d, 1H, J=9.0 Hz), 7.794 (d, 1H, J=9.0 Hz), 7.719 (t, 1H, J=7.5 Hz), 7.565 (t, 2H, J=8.0 Hz). MS-ESI (m/z): [M+H]+ calculated for C16H11BrNO4S, 392.0 (79Br) and 394.0 (81Br); found 391.8 (79Br) and 393.8 (81Br).

Workup

  1. temperaturethe reaction was cooled
  2. filtrationvacuum filtered
  3. customThe filtrate was collected
  4. concentrationconcentrated
  5. customleaving a yellow solid
  6. customPurification by silica gel with CHCl3 (100%)

Sources & evidence

ORD record
ord-38df3c9a5c09424f8c01971cb8286d09
Source dataset
uspto-grants-2011_04
Patent number
US07923562B2

Reaction notes

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