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

HRID 748925Notes

Reaction equation

HRID 748925 reaction equation
[C:1]([NH2:5])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[Br:13][C:14]1[CH:19]=[CH:18][C:17]([S:20](Cl)(=[O:22])=[O:21])=[CH:16][CH:15]=1>ClCCl.C(OCC)(=O)C>[Br:13][C:14]1[CH:19]=[CH:18][C:17]([S:20]([NH:5][C:1]([CH3:4])([CH3:3])[CH3:2])(=[O:22])=[O:21])=[CH:16][CH:15]=1

Participants

6

Reactant 3

HCID 6385Tert-ButylamineHCID 7396p-Bromobenzenesulfonyl chlorideHCID 8471Triethylamine

Product 1

HCID 796629N-t-Butyl 4-bromobenzenesulfonamideYield 86.2%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent3×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

Place t-butylamine (4.32 mL, 41.1 mmol), triethylamine (8.15 mL, 58.7 mmol) and dichloromethane (75 mL) in a 3-neck round bottom flask. Cool this stirring solution to 0° C. and add a solution of 4-bromobenzenesulfonyl chloride (10.0 g, 39.1 mmol) in dichloromethane (50 mL). Add additional dichloromethane (25 mL) and stir the reaction overnight, allowing it to warm to ambient temperature. Evaporate the reaction in vacuo. Suspend the resulting white solid in ethyl acetate and filter it. Concentrate the filtrate in vacuo and purify the resulting residue by flash chromatography (silica gel; 50%-80% gradient CH2Cl2 in hexanes) to provide 9.85 g of 4-bromo-N-tert-butyl-benzenesulfonamide (86%).

Workup

  1. customthe reaction overnight
  2. temperatureto warm to ambient temperature
  3. customEvaporate
  4. customthe reaction in vacuo
  5. filtrationfilter it
  6. concentrationConcentrate the filtrate in vacuo
  7. custompurify the resulting residue by flash chromatography (silica gel; 50%-80% gradient CH2Cl2 in hexanes)

Sources & evidence

ORD record
ord-8d902a682dc54efdb5a5ca7f8fd1df48
Source dataset
uspto-grants-2008_07
Patent number
US07399867B2

Reaction notes

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