Tert-Butylamine → N-(1,1-Dimethylethyl)benzenesulfonamide

HRID 1530492Notes

Reaction equation

HRID 1530492 reaction equation
[CH3:1][C:2]([NH2:5])([CH3:4])[CH3:3].C([O-])([O-])=O.[K+].[K+].[C:12]1([S:18](Cl)(=[O:20])=[O:19])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>C1COCC1.O>[C:2]([NH:5][S:18]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)(=[O:20])=[O:19])([CH3:4])([CH3:3])[CH3:1]

Participants

6

Reactant 3

HCID 6385Tert-ButylamineHCID 7369Benzenesulfonyl chlorideHCID 11430Potassium Carbonate

Product 1

HCID 314059N-(1,1-Dimethylethyl)benzenesulfonamideYield 90%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

2-Methylpropan-2-amine (5.8 g, 80 mmol) and K2CO3 (11 g, 80 mmol) were dissolved in a mixed solvents of THF and H2O (V:V=1:5, 30 ml). Benzenesulfonyl chloride (7.06 g, 40.0 mmol) was added drop wise at 0° C. to the above solution. After being stirred overnight, the resulting mixture was extracted with ethyl acetate (3×100 mL), washed with 1 N HCl (50 mL), sat. NaHCO3 (50 mL), sat. NaCl (50 mL), and dried over Na2SO4. After concentration, the residue was purified by silica gel chromatography eluting with a 0-10% gradient of EtOAc in petroleum ether to afford N-tert-butylbenzenesulfonamide (6.0 g, 90% yield) as white solid. 1H NMR (500 MHz, CDCl3): δ 7.93-7.91 (m, 2H), 7.54-7.47 (m, 3H), 5.06 (br, 1H), 1.22 (s, 9H)

Workup

  1. extractionthe resulting mixture was extracted with ethyl acetate (3×100 mL)
  2. washwashed with 1 N HCl (50 mL), sat. NaHCO3 (50 mL), sat. NaCl (50 mL)
  3. dry with materialdried over Na2SO4
  4. concentrationAfter concentration
  5. customthe residue was purified by silica gel chromatography
  6. washeluting with a 0-10% gradient of EtOAc in petroleum ether

Sources & evidence

ORD record
ord-43f3ef1fa9d64a13952bf97fddde050f
Source dataset
uspto-grants-2015_07
Patent number
US09090628B2

Reaction notes

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