Acetone → HCID 11195153, compound

HRID 239753Notes

Reaction equation

HRID 239753 reaction equation
[CH2:1]([NH2:6])[CH2:2][CH:3]([CH3:5])[CH3:4].[CH2:7]1[CH2:13][S:10](=[O:12])(=[O:11])[O:9][CH2:8]1.CC(C)=O>CC(=O)CC>[CH2:1]([NH:6][CH2:8][CH2:7][CH2:13][S:10]([OH:12])(=[O:11])=[O:9])[CH2:2][CH:3]([CH3:5])[CH3:4]

Participants

5

Reactant 3

HCID 180AcetoneHCID 7894IsoamylamineHCID 14264Propane sultone

Product 1

HCID 11195153HCID 11195153, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

Isoamylamine (4 mL, 34.5 mmol) was added to a solution of 1,3-propane sultone (4.7 g, 38 mmol) in 2-butanone (70 mL). The mixture was warmed to reflux. After 30 minutes, the mixture was too thick to stir. Acetone (15 mL) was added. The reflux was maintained for a total of 4 hours. The suspension was cooled at room temperature. The white solid was collected by filtration, rinsed with acetone (10 mL), then with ether (10 mL). Compound CH was obtained as a very light, fluffy white solid (4.48 g, 62% yield). m.p. 220° C.: decomposed. 1H NMR (500 MHz, D2O) δ 0.65 (d, J=6.3 Hz, 6H), 1.29 (q, J=7.7 Hz, 2H), 1.35-1.42 (m, J=6.6 Hz, 1H), 1.86 (qt, J=7.6 Hz, 2H), 2.74 (t, J=7.3 Hz, 2H), 2.81 (t, J=8.1 Hz, 2H), 2.93 (t, J=7.8 Hz, 2H). 13C NMR (125 MHz, D2O) δ 21.3, 21.4, 25.2, 34.2, 46.1, 46.2, 47.9

Workup

  1. temperatureThe mixture was warmed to reflux
  2. temperatureThe reflux was maintained for a total of 4 hours
  3. filtrationThe white solid was collected by filtration
  4. washrinsed with acetone (10 mL)

Sources & evidence

ORD record
ord-27cf489813bf4af0bee9b56348c8f2ee
Source dataset
uspto-grants-2014_02
Patent number
US08642801B2

Reaction notes

Loading…