Tert-Butylamine → N-tert-butyl-2-fluoro-4-methylbenzenesulfonamide

HRID 42335Notes

Reaction equation

HRID 42335 reaction equation
[C:1]([NH2:5])([CH3:4])([CH3:3])[CH3:2].[F:6][C:7]1[CH:12]=[C:11]([CH3:13])[CH:10]=[CH:9][C:8]=1[S:14](Cl)(=[O:16])=[O:15]>C1COCC1>[C:1]([NH:5][S:14]([C:8]1[CH:9]=[CH:10][C:11]([CH3:13])=[CH:12][C:7]=1[F:6])(=[O:15])=[O:16])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 6385Tert-ButylamineHCID 27784822-Fluoro-4-methylbenzenesulphonyl chloride

Product 1

HCID 11107608N-tert-butyl-2-fluoro-4-methylbenzenesulfonamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To an ice cooled solution of tert-butylamine (12.55 ml) in THF (60 ml) was added a solution of 2-fluoro-4-methylbenzene-1-sulfonyl chloride (5 g) in THF (25 ml), dropwise. After stirring for 15 min at 0° C., the reaction mixture was allowed to warm and stirred at room temperature for 2 hours. The HCl salt was removed by filtration and the filtrate was concentrated to give a yellow residue, which was triturated with Et2O and Hexanes to give 5.10 g N-tert-butyl-2-fluoro-4-methylbenzenesulfonamide as an off-white granular solid.

Workup

  1. temperatureto warm
  2. stirringstirred at room temperature for 2 hours
  3. customThe HCl salt was removed by filtration
  4. concentrationthe filtrate was concentrated
  5. customto give a yellow residue, which
  6. customwas triturated with Et2O and Hexanes

Sources & evidence

ORD record
ord-a7424409105145a4ae3d3ec5c4cf105f
Source dataset
uspto-grants-2013_09
Patent number
US08536187B2

Reaction notes

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