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

HRID 1648342Notes

Reaction equation

HRID 1648342 reaction equation
[C:1]1([S:7](Cl)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:11]([NH2:15])([CH3:14])([CH3:13])[CH3:12]>C(Cl)Cl>[C:11]([NH:15][S:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)(=[O:9])=[O:8])([CH3:14])([CH3:13])[CH3:12]

Participants

4

Reactant 2

HCID 6385Tert-ButylamineHCID 7369Benzenesulfonyl chloride

Product 1

HCID 314059N-(1,1-Dimethylethyl)benzenesulfonamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of benzenesulfonyl chloride in anhydrous CH2Cl2 (0.5M solution) cooled to 0° C. under N2 was added t-butylamine (2.2 equiv) slowly through a dropping funnel. After completion of addition, the reaction was stirred at toom temperature for 12 hours. The solvent was removed under reduced pressure, and the residue was extracted into ether and washed with 2N NaOH, H2O and brine. The organic phase was dried over anhydrous MgSO4 and concentrated in vacuo to afford the titled product, which was used directly in the next step.

Workup

  1. additionAfter completion of addition
  2. customThe solvent was removed under reduced pressure
  3. extractionthe residue was extracted into ether
  4. washwashed with 2N NaOH, H2O and brine
  5. dry with materialThe organic phase was dried over anhydrous MgSO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b80ef7096ed543a8bea75956d2d5491f
Source dataset
uspto-grants-1995_07
Patent number
US05436259

Reaction notes

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