1,4-Butane sultone → HCID 87095439, compound

HRID 239801Notes

Reaction equation

HRID 239801 reaction equation
[CH2:1]([NH2:12])[C:2]1[CH:11]=[CH:10][C:7]([O:8][CH3:9])=[C:4]([O:5][CH3:6])[CH:3]=1.[CH2:13]1[CH2:20][O:19][S:16](=[O:18])(=[O:17])[CH2:15][CH2:14]1>O1CCOCC1>[CH3:6][O:5][C:4]1[CH:3]=[C:2]([CH:11]=[CH:10][C:7]=1[O:8][CH3:9])[CH2:1][NH:12][CH:13]([CH3:20])[CH2:14][CH2:15][S:16]([OH:19])(=[O:18])=[O:17]

Participants

4

Reactant 2

HCID 154111,4-Butane sultoneHCID 79832Veratrylamine

Product 1

HCID 87095439HCID 87095439, compoundYield 18%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of veratrylamine (1.50 g, 9.0 mmol) in 1,4-dioxane (8 mL) was added 1,4-butane sultone (1.21 g, 8.5 mmol) at room temperature. The mixture was then heated at reflux for 2 hours. The reaction was cooled to room temperature. The solid was collected by filtration, washed with acetone (2×25 mL) and dried on pump. Yield: 18%. 1H NMR (D2O, 500 MHz) δ 6.96 (m, 3H), 4.04 (s, 2H), 3.74 (m, 6H), 2.95 (t, 2H, J=6.8 Hz), 2.80 (t, 2H, J=7.3 Hz), 1.68, (m, 4H). 13C (D2O, 125 MHz) δ ppm 149.19, 148.50, 123.82, 123.36, 113.25, 112.17, 55.91, 50.88, 50.24, 46.41, 24.55, 21.50. ES-MS 302 (M−1).

Workup

  1. temperatureThe mixture was then heated
  2. temperatureat reflux for 2 hours
  3. filtrationThe solid was collected by filtration
  4. washwashed with acetone (2×25 mL)
  5. customdried on pump

Sources & evidence

ORD record
ord-c3a17b9a16fd4aca9f79ab94b954d4b0
Source dataset
uspto-grants-2014_02
Patent number
US08642801B2

Reaction notes

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