Dimethylamine → 4-(Dimethylamino)butane-2-sulfonic acid

HRID 239794

Reaction equation

HRID 239794 reaction equation
[CH3:1][CH:2]1[S:6](=[O:8])(=[O:7])[O:5][CH2:4][CH2:3]1.[CH3:9][NH:10][CH3:11]>>[CH3:9][N:10]([CH3:11])[CH2:4][CH2:3][CH:2]([S:6]([OH:5])(=[O:8])=[O:7])[CH3:1]

Participants

3

Reactant 2

HCID 674DimethylamineHCID 707161,2-Oxathiolane, 3-methyl-, 2,2-dioxide

Product 1

HCID 587946244-(Dimethylamino)butane-2-sulfonic acid

Conditions

Temperature
0 °C

Procedure

2,4-butanesultone (1.27 g, 8.9 mmol) was added to an ice-chilled solution of dimethylamine (40% w/w in water). The solution was stirred at 0° C. for 4 hours. The solvent was evaporated in vacuo until complete dryness. The solid was washed with acetone (50 mL), collected by filtration and dried in vacuo. 1H NMR (D2O, 500 MHz) δ ppm 3.18 (t, 2H, J=8.1 Hz), 2.85 (m, 1H), 2.76 (s, 6H), 2.09 (m, 1H), 1.81 (m, 1H), 1.17 (d, 3H, J=7.3 Hz). 13C (D2O, 125 MHz) δ ppm 55.65, 53.05, 42.88, 26.72, 14.81. ES-MS182a (M+1).

Workup

  1. customThe solvent was evaporated in vacuo until complete dryness
  2. washThe solid was washed with acetone (50 mL)
  3. filtrationcollected by filtration
  4. customdried in vacuo

Sources & evidence

ORD record
ord-114e0e33c64c4fbda180f55083797151
Source dataset
uspto-grants-2014_02
Patent number
US08642801B2

Linked notes

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