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

HRID 252263Notes

Reaction equation

HRID 252263 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.O>[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

5

Reactant 2

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

Product 1

HCID 79380454-bromo-N-tert-butyl-3-methylbenzenesulfonamideYield 89.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirred, ice-cold solution of 4-bromo-3-methyl-benzenesulfonyl chloride (11 g, 40.8 mmol) and N′N-diisopropylethylamine (8.5 ml, 49 mmol, 1.2 equiv.) in dichloromethane was added dropwise tert. butylamine (5.2 ml, 49 mmol, 1.2 equiv.). After two hours at room temp., the reaction mixture was diluted with water and extracted with dichloromethane. The organic extracts were concentrated under reduced pressure, the residue stirred with n-heptane and filtered to obtain 11.2 g of the desired compound as a yellow solid. MS (ES): m/e 304.2 (M−H)

Workup

  1. extractionextracted with dichloromethane
  2. concentrationThe organic extracts were concentrated under reduced pressure
  3. filtrationfiltered

Sources & evidence

ORD record
ord-ae70de4a612a4384b29d889db30582eb
Source dataset
uspto-grants-2011_01
Patent number
US07868030B2

Reaction notes

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