Tert-Butylamine → N-t-Butyl 4-bromobenzenesulfonamide

HRID 1003598Notes

Reaction equation

HRID 1003598 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8](Cl)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[C:12]([NH2:16])([CH3:15])([CH3:14])[CH3:13]>C1COCC1>[C:12]([NH:16][S:8]([C:5]1[CH:6]=[CH:7][C:2]([Br:1])=[CH:3][CH:4]=1)(=[O:10])=[O:9])([CH3:15])([CH3:14])[CH3:13]

Participants

4

Reactant 2

HCID 6385Tert-ButylamineHCID 7396p-Bromobenzenesulfonyl chloride

Product 1

HCID 796629N-t-Butyl 4-bromobenzenesulfonamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-bromobenzenesulfonyl chloride (100.2 g) in THF (400 mL) was added t-butylamine (125 mL). An exothermic reaction results with gentle refluxing of the solvent. After 30 min, the bath was removed and the mixture was allowed to warm to r.t. Isopropyl acetate (400 mL) was added and the mixture was washed twice with water. The aqueous phase was back-extracted with ethyl acetate and the combined organics were dried (sodium sulfate) and concentrated to provide the title compound as a solid (112.9 g).

Workup

  1. customAn exothermic reaction
  2. customresults
  3. temperaturewith gentle refluxing of the solvent
  4. customthe bath was removed
  5. additionIsopropyl acetate (400 mL) was added
  6. washthe mixture was washed twice with water
  7. extractionThe aqueous phase was back-extracted with ethyl acetate
  8. dry with materialthe combined organics were dried (sodium sulfate)
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-c91bfd4549a54c0992b4742fd4e1a0ae
Source dataset
uspto-grants-2000_04
Patent number
US06046217

Reaction notes

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