Tert-Butylamine → 4-bromo-N-tert-butyl-3-methylbenzenesulfonamide

HRID 42338Notes

Reaction equation

HRID 42338 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8](Cl)(=[O:10])=[O:9])=[CH:4][C:3]=1[CH3:12].[C:13]([NH2:17])([CH3:16])([CH3:15])[CH3:14]>ClCCl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:17][C:13]([CH3:16])([CH3:15])[CH3:14])(=[O:10])=[O:9])=[CH:4][C:3]=1[CH3:12]

Participants

4

Reactant 2

HCID 6385Tert-ButylamineHCID 27375034-Bromo-3-methylbenzene-1-sulfonyl chloride

Product 1

HCID 79380454-bromo-N-tert-butyl-3-methylbenzenesulfonamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 4-bromo-3-methylbenzene-1-sulfonyl chloride (1.50 g) in dichloromethane (10 ml) at 0° C. was added tert-butylamine (1.5 ml). The reaction mixture was allowed to warm to and stirred at room temperature overnight. The reaction mixture was diluted with dichloromethane, washed with 1N HCl and with sat. aq. NaHCO3 solution. The organic layer was dried (MgSO4) and concentrated to give 1.20 g 4-bromo-N-tert-butyl-3-methylbenzenesulfonamide as a white solid.

Workup

  1. temperatureto warm to and
  2. washwashed with 1N HCl and with sat. aq. NaHCO3 solution
  3. dry with materialThe organic layer was dried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-bd9f92c3510b42e3996f2b82e0326c69
Source dataset
uspto-grants-2013_09
Patent number
US08536187B2

Reaction notes

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