Tert-Butylamine → N-tert-Butyl 4-Nitrophenylsulfonamide

HRID 898748Notes

Reaction equation

HRID 898748 reaction equation
[C:1]([NH2:5])([CH3:4])([CH3:3])[CH3:2].[N+:6]([C:9]1[CH:14]=[CH:13][C:12]([S:15](Cl)(=[O:17])=[O:16])=[CH:11][CH:10]=1)([O-:8])=[O:7]>C1COCC1>[C:1]([NH:5][S:15]([C:12]1[CH:11]=[CH:10][C:9]([N+:6]([O-:8])=[O:7])=[CH:14][CH:13]=1)(=[O:16])=[O:17])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 6385Tert-ButylamineHCID 74044-Nitrobenzenesulfonyl chloride

Product 1

HCID 796974N-tert-Butyl 4-NitrophenylsulfonamideYield 97%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of tert-butylamine (0.47 L, 6.4 mol) in THF (0.55 L) is slowly added, at 0° C., a solution of 4-nitrobenzenesulfonyl chloride (50 g, 0.23 mol) in THF (0.55 L) and the resulting mixture is stirred for 24 h at room temperature. The solvent is removed and the residue is taken up in a CHCl3/0.5 N HCl mixture, the layers are separated and the aqueous phase is extracted with CHCl3. The combined organic extracts are washed with H2O and brine and dried over MgSO4. The solvent is removed, yielding 56.3 g of a yellowish solid which is directly used in the next reaction (yield: 97%).

Workup

  1. customThe solvent is removed
  2. customthe layers are separated
  3. extractionthe aqueous phase is extracted with CHCl3
  4. washThe combined organic extracts are washed with H2O and brine
  5. dry with materialdried over MgSO4
  6. customThe solvent is removed

Sources & evidence

ORD record
ord-8e0bf814a36c4acdbd953b764e2b515b
Source dataset
uspto-grants-2008_04
Patent number
US07351836B2

Reaction notes

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