Tert-Butylamine → 3-(tert-Butylamino)propylsulfonic acid

HRID 446628Notes

Reaction equation

HRID 446628 reaction equation
[CH2:1]1[CH2:7][S:4](=[O:6])(=[O:5])[O:3][CH2:2]1.[C:8]([NH2:12])([CH3:11])([CH3:10])[CH3:9]>C1(C)C=CC=CC=1>[C:8]([NH:12][CH2:2][CH2:1][CH2:7][S:4]([OH:3])(=[O:6])=[O:5])([CH3:11])([CH3:10])[CH3:9]

Participants

4

Reactant 2

HCID 6385Tert-ButylamineHCID 14264Propane sultone

Product 1

HCID 111715633-(tert-Butylamino)propylsulfonic acid

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 1,3-propanesultone (20 g, 0.164 g) in toluene (100 mL) was added tert-butylamine (90 mL, 62.1 g, 0.85 mol). The mixture was stirred under gentle reflux for 1 hour. The precipitate was filtered, washed with diethyl ether and dried at 20-25° C. Yield 3-(tert-butylamino)propylsulfonic acid 32 g (approximately 100%), as white microcrystals, mp above 280° C., 1H NMR (D2O) δ 1.33 (s, 9H), 2.07 (p, J=7.6 Hz, 2H), 2.99 (t, J=7.6 Hz, 2H), 3.15 (t, J=7.7 Hz, 2H); 13C NMR δ 21.3, 24.3, 39.4, 47.4, 56.5.

Workup

  1. temperatureunder gentle reflux for 1 hour
  2. filtrationThe precipitate was filtered
  3. washwashed with diethyl ether
  4. customdried at 20-25° C

Sources & evidence

ORD record
ord-8a9eefd479d54572a3bfbdd4137f659c
Source dataset
uspto-grants-2013_07
Patent number
US08480795B2

Reaction notes

Loading…