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

HRID 400301Notes

Reaction equation

HRID 400301 reaction equation
[C:1]([NH2:5])([CH3:4])([CH3:3])[CH3:2].[C:6]1([S:12](Cl)(=[O:14])=[O:13])[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1>C1COCC1>[C:1]([NH:5][S:12]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)(=[O:14])=[O:13])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 6385Tert-ButylamineHCID 7369Benzenesulfonyl chloride

Product 1

HCID 314059N-(1,1-Dimethylethyl)benzenesulfonamideYield 95.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a cooled (0° C.) solution of tert-butylamine (42.9 mL, 410.6 mmol) in THF (840 mL) was added dropwise benzenesulfonyl chloride (26.2 mL, 205 mmol) and the reaction mixture was stirred at room temperature under an argon atmosphere for 6 h. The mixture was then filtered and the collected solid washed with THF. The filtrate was concentrated, redissolved in CH2Cl2 and washed with 0.1N HCl and H2O. The organic solution was dried and concentrated to afford the desired product (41.8 g, 95%).

Workup

  1. filtrationThe mixture was then filtered
  2. washthe collected solid washed with THF
  3. concentrationThe filtrate was concentrated
  4. dissolutionredissolved in CH2Cl2
  5. washwashed with 0.1N HCl and H2O
  6. customThe organic solution was dried
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-1b6044d52b904ce0a18f29ce5dce3756
Source dataset
uspto-grants-1998_10
Patent number
US05827863

Reaction notes

Loading…