Tert-Butylamine → 1-Butanesulfonic acid, 4-[(1,1-dimethylethyl)amino]-

HRID 239795Notes

Reaction equation

HRID 239795 reaction equation
[C:1]([NH2:5])([CH3:4])([CH3:3])[CH3:2].[CH2:6]1[CH2:13][O:12][S:9](=[O:11])(=[O:10])[CH2:8][CH2:7]1>O1CCCC1>[C:1]([NH:5][CH2:13][CH2:6][CH2:7][CH2:8][S:9]([OH:12])(=[O:11])=[O:10])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 6385Tert-ButylamineHCID 154111,4-Butane sultone

Product 1

HCID 112642731-Butanesulfonic acid, 4-[(1,1-dimethylethyl)amino]-

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of tert-butylamine (1.0 mL, 9.5 mmol) in tetrahydrofuran (4 mL) was added 1,4-butane sultone (1.36 g, 10.0 mmol) at room temperature. The solution was stirred at reflux for 2 hours. The reaction was cooled to room temperature. The solid was collected by filtration, washed with acetone (2×20 mL) and dried in vacuo. Yield: 690 mg (34%). 1H NMR (D2O, 500 MHz) δ ppm 2.92 (t, 2H, J=7.1 Hz), 2.82 (t, 2H, J=7.1 Hz), 1.68 (m, 4H), 1.22 (s, 9H). 13C (D2O, 125 MHz) δ ppm 57.07, 50.30, 40.95, 25.28, 24.96, 21.62. ES-MS 210 (M−1).

Workup

  1. temperatureat reflux for 2 hours
  2. filtrationThe solid was collected by filtration
  3. washwashed with acetone (2×20 mL)
  4. customdried in vacuo

Sources & evidence

ORD record
ord-64e760af991a4103ae876b81f37a9664
Source dataset
uspto-grants-2014_02
Patent number
US08642801B2

Reaction notes

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