Acetonitrile → N-(1,1-Dimethylethyl)benzenesulfonamide

HRID 504272Notes

Reaction equation

HRID 504272 reaction equation
[C:1]1([S:7](Cl)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(=O)([O-])[O-].[K+].[K+].C(#N)C.[C:20]([NH2:24])([CH3:23])([CH3:22])[CH3:21]>>[C:20]([NH:24][S:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)(=[O:9])=[O:8])([CH3:23])([CH3:22])[CH3:21]

Participants

5

Reactant 4

HCID 6342AcetonitrileHCID 6385Tert-ButylamineHCID 7369Benzenesulfonyl chlorideHCID 11430Potassium Carbonate

Product 1

HCID 314059N-(1,1-Dimethylethyl)benzenesulfonamideYield 100.2%

Procedure

To a solution of benzenesulfonyl chloride (722 μL, 0.00566 mol), potassium carbonate (0.939 g, 0.00679 mol) in acetonitrile (15 mL, 0.29 mol) was added tert-butylamine (0.652 mL, 0.00623 mol). The resulting mixture was stirred at r.t. for 30 minutes, followed by filtration and concentration. The resulting residue was diluted with ethyl acetate, and the resulting solution was washed with water then with brine, then dried with MgSO4 followed by concentration. The crude material was purified by flash chromatography on silica gel with 40% AcOEt in hexanes to give the desired compound (1.21 g, 85% yield). MS (ESI): 236.0 (M+Na+).

Workup

  1. filtrationfollowed by filtration and concentration
  2. additionThe resulting residue was diluted with ethyl acetate
  3. washthe resulting solution was washed with water
  4. dry with materialwith brine, then dried with MgSO4
  5. concentrationfollowed by concentration
  6. customThe crude material was purified by flash chromatography on silica gel with 40% AcOEt in hexanes

Sources & evidence

ORD record
ord-436000b76b36439690536a13d6611f57
Source dataset
uspto-grants-2010_08
Patent number
US07776874B2

Reaction notes

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