Propane sultone → 1-Propanesulfonic acid, 3-[(1,1-dimethylethyl)methylamino]-

HRID 239750Notes

Reaction equation

HRID 239750 reaction equation
[CH3:1][NH:2][C:3]([CH3:6])([CH3:5])[CH3:4].[CH2:7]1[CH2:13][S:10](=[O:12])(=[O:11])[O:9][CH2:8]1>CC(C)=O>[CH3:1][N:2]([CH2:8][CH2:7][CH2:13][S:10]([OH:12])(=[O:11])=[O:9])[C:3]([CH3:6])([CH3:5])[CH3:4]

Participants

4

Reactant 2

HCID 14264Propane sultoneHCID 84552N-Methyl-tert-butylamine

Product 1

HCID 112872631-Propanesulfonic acid, 3-[(1,1-dimethylethyl)methylamino]-

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of N-methyl-tert-butylamine (2.0 g, 22.9 mmol) in acetone (25 mL) was slowly added 1,3-propane sultone (2.72 g, 21.8 mmol). The mixture was stirred at reflux for 3 h. The reaction mixture was cooled to room temperature. The solid material was collected by filtration, washed with acetone (2×25 mL). The crude product was suspended in 80% Acetone/EtOH. The suspension was stirred at reflux for 30 seconds. The solid product was collected by filtration, and dried in a vacuum oven (50° C.), to afford compound EN (2.9 g, 65%). 1H NMR (DMSO, 500 MHz) δ ppm 9.40 (s (broad), 1H), 3.45 (m, 1H), 2.85 (m, 1H), 2.59 (m, 5H), 1.99 (m, 2H), 1.28 (s, 9H). 13C NMR (DMSO, 125 MHz) δ ppm 63.23, 51.12, 49.73, 34.79, 25.50, 21.72. ES-MS 208 (M−1).

Workup

  1. temperatureat reflux for 3 h
  2. filtrationThe solid material was collected by filtration
  3. washwashed with acetone (2×25 mL)
  4. stirringThe suspension was stirred
  5. temperatureat reflux for 30 seconds
  6. filtrationThe solid product was collected by filtration
  7. customdried in a vacuum oven (50° C.)
  8. customto afford compound EN (2.9 g, 65%)

Sources & evidence

ORD record
ord-5384d2173af243eaafcb7538305a13c5
Source dataset
uspto-grants-2014_02
Patent number
US08642801B2

Reaction notes

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