Tert-Butylamine → N-tert-butyl-4-propylbenzenesulfonamide

HRID 257587Notes

Reaction equation

HRID 257587 reaction equation
[CH2:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10](Cl)(=[O:12])=[O:11])=[CH:6][CH:5]=1)[CH2:2][CH3:3].[C:14]([NH2:18])([CH3:17])([CH3:16])[CH3:15]>C(Cl)Cl>[C:14]([NH:18][S:10]([C:7]1[CH:8]=[CH:9][C:4]([CH2:1][CH2:2][CH3:3])=[CH:5][CH:6]=1)(=[O:12])=[O:11])([CH3:17])([CH3:16])[CH3:15]

Participants

4

Reactant 2

HCID 6385Tert-ButylamineHCID 27372224-N-Propylbenzenesulphonyl chloride

Product 1

HCID 6470063N-tert-butyl-4-propylbenzenesulfonamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-n-propylbenzenesulfonyl chloride (Lancaster) in anhydrous CH2Cl2 (0.5M solution) cooled to 0° C. under N2 was added t-butylamine (2.2 equivalents) slowly through a dropping funnel. After complete addition, the reaction was stirred at room temperature for 12 hours. The CH2Cl2 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 title compound; TLC in 3:1 hexane-EtOAc (Rf =0.46) (3:1 hexane-EtOAc). 200 MHz 1H NMR (CDCl3) δ0.93 (t, 3H), 1.22 (s, 9H), 1.62 (m, 2H), 2.65 (t, 2H), 4.67 (br s, 1H), 7.27 (d, 2H), 7.79 (d, 2H).

Workup

  1. additionAfter complete addition
  2. customThe CH2Cl2 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-4e22a639b85245e49b56e6776b28ff6e
Source dataset
uspto-grants-1993_11
Patent number
US05262412

Reaction notes

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