Tert-Butylamine → 5-Bromo-N-tert-butylpyridine-3-sulfonamide

HRID 384743Notes

Reaction equation

HRID 384743 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([S:8](Cl)(=[O:10])=[O:9])[CH:5]=[N:6][CH:7]=1.[C:12]([NH2:16])([CH3:15])([CH3:14])[CH3:13]>N1C=CC=CC=1.Cl>[Br:1][C:2]1[CH:3]=[C:4]([S:8]([NH:16][C:12]([CH3:15])([CH3:14])[CH3:13])(=[O:10])=[O:9])[CH:5]=[N:6][CH:7]=1

Participants

5

Reactant 2

HCID 6385Tert-ButylamineHCID 203244745-Bromopyridine-3-sulfonyl chloride

Product 1

HCID 617949515-Bromo-N-tert-butylpyridine-3-sulfonamideYield 42.9%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 1049PyridineSolvent

Procedure

To a solution of 5-bromopyridine-3-sulfonyl chloride (5 g, 17 mmol) in pyridine (10 mL) at 0° C. was added tert-butylamine (3.6 mL, 2 equiv., 34 mmol). The reaction mixture was allowed to warm to room temperature and then heated to 40° C. for 14 h. After this time the crude reaction mixture was again cooled to 0° C. and diluted with dilute HCl (0.05M, 40 mL). The reaction was stirred at 0° C. for 30 min and the resulting precipitate collected by filtration. The solid was washed with water and dried to afford the title compound as a yellow solid (2.12 g, 7.3 mmol, 42%). No further purification was required.

Workup

  1. temperatureheated to 40° C. for 14 h
  2. customAfter this time the crude reaction mixture
  3. temperaturewas again cooled to 0° C.
  4. filtrationthe resulting precipitate collected by filtration
  5. washThe solid was washed with water
  6. customdried

Sources & evidence

ORD record
ord-590820fc38de4c79b6d98bc8a97bdbf3
Source dataset
uspto-grants-2013_02
Patent number
US08367830B2

Reaction notes

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